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Students get through the TN Board 12th Chemistry Important Questions Chapter 15 Chemistry in Everyday Life which is useful for their exam preparation.

TN State Board 12th Chemistry Important Questions Chapter 15 Chemistry in Everyday Life

Answer the following questions.

Question 1.
Define the term chemotherapy.
Answer:
The specific treatment of a disease by using medicine is known as chemotherapy.

Question 2.
Define therapeutic index? What is its use?
Answer:
It is defined as the ratio between the maximum tolerated dose of a drug (above which it becomes toxic) and the minimum curative dose (below which it becomes ineffective). Higher the values of therapeutic index safer is the drug.

Question 3.
Explain the term, target molecules or drug targets as used in medicinal chemistry.
Answer:
Drugs interact with macromolecules like proteins, carbohydrates, lipids, nucleic acids. Hence they are called target drugs. Proteins perform several roles in the body. Enzymes are crucial in communication systems and are called receptors.

Question 4.
Give examples of drugs that are grouped based on the biological effect that they produce on the recipient.
Answer:

1. Antibiotic drugs: Amoxycillin, ampicillin, cefixime, cefpodoxime, erythromycin, tetracycline, etc.
2. Antihypertensive drugs: propranolol, atenolol, metoprolol succinate, amlodipine, etc.

Question 5.
Streptomycin and erythromycin are classified in the same group. Justify the statement.
Answer:
Both inhibit the protein synthesis (target process) in bacteria and are classified in the same group. However, the mode of action is different. Streptomycin inhibits the initiation of protein synthesis while erythromycin prevents the incorporation of new amino acids to the protein. These drugs are grouped based on the biological system/process that targets the recipient.

Question 6.
Write a short note on enzymes as drug targets.
Answer:
In all living systems, the biochemical reactions are catalysed by enzymes. Hence, these enzyme actions are highly essential for the normal functioning of the system. If their normal enzyme activity is inhibited, then the system will be affected. This principle is usually applied to kill many pathogens.
In enzyme catalysed reactions, the substrate molecule binds to the active site of the enzyme by means of the weak interaction such as hydrogen bonding, Van der waals force etc., between the amino acids present in the active site and the substrate.
When a drug molecule that has a similar geometry (shape)as the substrate is administered, it can also bind to the enzyme and inhibit its activity. In other words, the drug acts as an inhibitor to the enzyme catalyst. These types of inhibitors are often called competitive inhibitors.
In certain enzymes, the inhibitor molecule binds to a different binding site, which is commonly referred to as an allosteric site and causes a change in its active site geometry (shape). As a result, the substrate cannot bind to the enzyme. These types of inhibitors are called allosteric inhibitors.

Question 7.
How do drugs interact with targets? (or) Give a brief account of drug-target interaction.
Answer:
Drugs interact with macromolecules like carbohydrates, proteins, nucleic acids lipids present in the cell. The macromolecules perform various functions in the body, eg: Proteins perform several roles in the body.

1. Proteins that act as biological catalysts are called enzymes.
2. Proteins that are crucial to a communication system in the body are called receptors.
3. Proteins that carry polar molecules across the membranes are called carrier proteins.

In their catalytic activity enzymes perform two major functions.

1. The first function of an enzyme is to hold the substrate molecule for a chemical reaction.
2. The second function of the enzyme is to provide functional groups which will attack the substrate to carry out the chemical reaction.

Question 8.
How do drugs interact with enzymes? (or) Give a brief account of drug-enzyme interaction.
Answer:
Drugs that inhibit any two of the activities mentioned in Q7 are called enzyme inhibitors. Enzyme inhibitors can block the binding site thereby preventing the binding of the substrate to the active site and hence inhibit the catalytic activity of enzymes.
Drugs inhibit the attachment of natural substrate on active site in two ways:

1. Drugs that compete with the natural substrate for their attachment on the active sites of enzymes are called competitive inhibitors.
2. Same drugs, however, do not bind on the active site but bind to different sites of the enzyme which is called the allosteric site.

This binding of the drug (inhibitor) at the allosteric site changes the shape of the active site of the enzyme in such a way that the natural substrate cannot recognize it. Such enzymes are called noncompetitive inhibitors.
If the bond between an enzyme and the drug (inhibitor) is a strong covalent bond that cannot be broken easily then the enzyme is blocked permanently. The body then degrades the enzyme-drug (inhibitor) complex and synthesis the new enzyme.

Question 9.
Explain the terms (i) Competitive inhibitors, (ii) Allosteric inhibitors.
Answer:
(i) Competitive inhibitors:
In enzyme-catalyzed reactions, the substrate molecule binds to the active site of the enzyme by means of the weak interaction such as hydrogen bonding, Van der Waals force etc., between the amino acids present in the active site and the substrate. When a drug molecule that has a similar geometry (shape)as the substrate is administered, it can also bind to the enzyme and inhibit its activity. In other words, the drug acts as an inhibitor to the enzyme catalyst. These types of inhibitors are often called competitive inhibitors.
(ii) Allosteric inhibitors:
In certain enzymes, the inhibitor molecule binds to a different binding site, which is commonly referred to as an allosteric site and causes a change in its active site geometry (shape). As a result, the substrate cannot bind to the enzyme. These types of inhibitors are called allosteric inhibitors.

Question 10.
Explain the term (i) Chemical messengers, (ii) Receptor, (iii) Antagonists, (iv) Agonists.
Answer:
(i) Chemical messengers: In the body, messages between two neurons (nerve cells) or that between neurons and muscles are communicated through a certain chemicals in substances called chemical messengers.
(ii) Receptors: Receptors are proteins that are crucial to the communication system in the body.
(iii) Antagonists: Drugs that bind to the receptor site and inhibit its natural function are called antagonists. These are useful when blocking of the message is required.
(iv) Agonists: Drugs that mimic (imitate) the natural chemical messengers by switching on the receptor are called agonists. These are useful when there is a lack of natural chemical messengers.

Question 11.
Mention the various types of chemical messengers and explain how they act?
Answer:
There are two types of chemical messengers.
(i) Hormones (ii) Neurotransmitters.

1. Hormones are a group of biomolecules
   which are produced in the ductless (endocrine) glands. These enter into the bloodstream and travel to different parts of the body activating all the receptors. which recognize them for message
   transfer. They are not deactivated quickly. Adrenaline is an example of a hormone.
2. Neurotransmitters: Nerves transfer messages through neurotransmitters. These bind to the receptor (target) for a very short time to transfer the message to it and depart quickly unchanged after transferring the message. The receptor then forwards the message inside the cell. After leaving the active site, neurotransmitters undergo degradation and lose their capacity to transfer messages.

Question 12.
With reference to which classification has the statement “ranitidine, is an antacid” been given?
Answer:
This statement refers to the classification of drugs according to pharmacological effect because drugs that will be used to counteract the excess acid in the stomach will be called antacids.

Question 13.
List two major classes of antibiotics with an example of each class.
Answer:

Question 14.
What are tranquilizers? How do they act? Give two examples.
Answer:
Tranquilizers are neurologically active drugs. They are used in the treatment of stress anxiety, sleep disorders, and mental diseases. They act on the central nervous system by blocking the neurotransmitter dopamine in the main Dizephan, alprazolam is the examples.

Question 15.
Give two examples for each (i) Anti-inflammatory drugs (ii) Antipyretics (iii) nonsteroidal Anti-inflammatory drugs.
Answer:
(i) AntiinflammatorydrugsAcetaminophen or paracetamol, ibuprofen, aspirin.
(ii) Antipyretics: Acetylsalicylic acid (aspirin), Acetaminophen or Paracetamol.
(iii) Nonsteroidal anti-inflammatory drugs: Ibuprofen.

Question 16.
Mention an important difference between non-narcotic analgesics and narcotic analgesics.
Answer:
Non-narcotic analgesics are non-addictive drugs while narcotic analgesics are addictive drugs.

Question 17.
Give two examples of narcotic analgesics.
Answer:
Morphine and codeine are examples of narcotic analgesics.

Question 18.
Give two examples for local anesthetics.
Answer:
Procaine and Lidocaine.

Question 19.
Name the anesthetics used for major surgical procedures.
Answer:
Propofol and Isoflurane.

Question 20.
Give examples of antacids. How do antacids function in case of acidity?
Answer:
Milk of magnesia, sodium bicarbonate, aluminum hydroxide, ranitidine, cimetidine, omeprazole, rabeprazole are examples of antacid. They neutralize the acid in the stomach that causes acidity.

Question 21.
What are antihistamines? Give two examples.
Answer:
Antihistamines are drugs that provide relief to allergic effects, eg: cetirizine, levocetirizine.

Question 22.
What are antimicrobials? Give two examples.
Answer:
Drugs that are used to cure diseases caused by microbes or microorganisms such as bacteria, viruses, fungi, etc are called antimicrobials. These include antibacterials, antifungal, and viral agents.
eg: penicillin, erythromycin.

Question 123
How does (i) β lactams and (ii) macrolides function as antimicrobials?
Answer:
(i) β – lactam inhibits cell wall biosynthesis.
(ii) Macrolides target bacterial ribosomes and prevent protein production.

Question 24.
Give examples for β – lactam and macrolides antimicrobials.
Answer:
β – lactams: Penicillin, ampicillin, cephalosporins, carbapenems, and monobactams.
Macrolides: Erythromycin, azithromycin.

Question 25.
What are the uses of β-lactam and macrolide antimicrobials?
Answer:
Beta lactams: They are used to treat skin infections, dental infections ear infections, respiratory tract infections.
Macrolides: They are used to treat respiratory tract infectious, genital, gastrointestinal tract and skin infectious.

Question 26.
Give examples for ‘Fluoroquinolones’ and mention their uses.
Answer:
Clinafloxacin, ciprofloxacin, levofloxacin are examples of fluoroquinolones. They are used to treat urinary tract infections, skin infections, and respiratory infections.

Question 27.
How do tetracyclines class of antibiotics function? Mention their uses.
Answer:
Doxycycline, minocycline, oxytetracycline are examples of the tetracyclines group of antibiotics. They inhibit the bacterial protein synthesis via interaction with the 30S subunit of the bacterial ribosome.
They are used in the treatment of peptic ulcers, infection of the respiratory tract, etc.

Question 28.
What are aminoglycosides? Give examples.
Answer:
Aminoglycosides are a type of antibiotics that bind to the 30S subunit of the bacterial ribosome, thus stopping bacteria from making proteins.
eg: kanamycin, gentamycin neomycin.

Question 29.
What are food additives? Give examples.
Answer:
The substances which are not naturally a part of the food and are added to improve the quality of food are called food additives. The substances enhance the nutritive, sensory, and practical value of the food. They also increase the shelf life of food.
Important categories of food additives:

1. Aroma compounds
2. Food colors
3. Preservatives
4. Stabilizers
5. Artificial Sweeteners
6. Antioxidants
7. Buffering substances
8. Vitamins and minerals

Question 30.
What are food preservatives?
Answer:
Chemical substances which are used to protect food against bacteria, yeasts and molds are called preservatives, eg: sodium metabisulphite (sodium meta sulfite), sodium benzoate etc.

Question 31.
Name the preservative used in the preparation of pickles and vegetables.
Answer:

1. Acetic acid for pickles
2. Sodium meta-sulphate for fresh vegetables and fruits.

Question 32.
Name the chemicals which are used as emulsifiers.
Answer:
Sucrose esters with palmitic and steric esters are used as emulsifiers.

Question 33.
Name the physical methods used in the preservative of food.
Answer:

1. Heat treatment (pasteurization and sterilizations)
2. Cold treatment (chilling and freezing)
3. Drying (dehydration)
4. Irradiation is used to preserve food.

Question 34.
What are antioxidants? Give examples.
Answer:
Antioxidants are substances that retard the oxidative deteriorations of food. Food containing fats and oils is easily oxidized and turns rancid. To prevent the oxidation of the fats and oils, chemical BHT(butylhydroxytoluene), BHA(Butylated hydroxyanisole) are added as food additives. They are generally called antioxidants.

Question 35.
How do antioxidants prevent the oxidation of food?
Answer:
They readily undergo oxidation by reacting with free radicals generated by the oxidation of oils, thereby stop the chain reaction of oxidation of food. Sulphur dioxide and sulphites are also used as food additives. They act as anti-microbial agents, antioxidants, and enzyme inhibitors.

Question 36.
Define “Total Fatty Matter (TFM). What is its use?
Answer:
It is defined as the total amount of fatty matter that can be separated from a sample after splitting with mineral acids. The higher the TFM quantity in the soap better is its quality.

Question 37.
What is an anionic detergent?
Answer:
Anionic detergent: They are so named because a large part of their molecules are anions and it is the anionic part of the molecule is involved in the cleansing actions. These are sodium salts of sulphonated long-chain alcohols or hydrocarbon. For example, sodium lauryl sulphate, sodium dodecyl benzene sulphonate, etc. Anionic detergents are used is household work and in toothpastes.

Question 38.
What is cationic detergents?
Answer:
Cationic detergent: They are so-called because a large part of their molecule are cations and it is the cationic part of the molecule is involved in the cleansing action cationic detergents are quaternary ammonium salts of amines, with acetates, chlorides, or bromides as anions. Cetyl trimethyl ammonium bromide is a cationic detergent and is used in hair conditioners. Cationic detergents have germicidal properties and are expensive, therefore they are of limited use.

Question 39.
What is Non-ionic detergent?
Answer:
Non- ionic detergents: These detergents do not contain any ion. These are esters of high molecular weight alcohols. One such detergent is formed when stearic acid reacts with polyethylene glycol. Liquid dishwashing detergent are nonionic type.

Question 40.
Explain the terms monomer and polymer and polymerization.
Answer:
Monomer: Simple and reactive molecules from which polymers are prepared either by addition or condensation are called monomers, eg: Vinyl chloride, ethene, formaldehyde, acrylonitrile, phenol, etc.
Polymers: These are compounds of high molecular mass formed by the combination of a large number of simple molecules called monomers. The process by which monomers are converted to polymers is called polymerization.

Question 41.
What are synthetic and natural polymers? Give two examples for each type.
Answer:
Synthetic polymers are man-made polymers prepared in the laboratory, eg: polyethylene, Teflon, nylon, etc.
Natural polymers are naturally occurring polymers, mostly in plants, animals, etc. eg: Protein natural rubber, etc.

Question 42.
In which classes, the polymers are classified on the basis of molecular forces.
Answer:
On the basis of intermolecular forces of attraction operating between different polymers chains, polymers are classified as

1. Elastomers
2. Fibres
3. Thermoplastic polymers
4. Thermo setting polymers

Question 43.
Write names of monomers of the following polymers and classify them as addition or condensation polymers.
(a) Teflon, (b) Bakelite, (c) Natural rubber
Answer:

Question 44.
What is the role of benzoyl peroxide in the polymerization of ethene?
Answer:
Benzoyl peroxide is an initiator. It forms a free radical.

Question 45.
What are LDPE and HDPE? How are they prepared?
Answer:
LDPE is low-density polyethylene. It is obtained by the polymerization of ethene under high pressure of 1000 – 2000 atm at 350 – 570 K in the presence of an initiator. HDPE is called high-density polyethylene. It is obtained by the polymerization of ethene in the presence of Ziegler – Natta catalyst at 333 – 343 K under 6-7 atm.

Question 46.
Write the structure of the monomers of the following polymers, (i) PVC, (ii) Polypropene, (iii) PAN, (iv) Nylon – 6.
Answer:

Question 47.
Give examples each of (i) addition polymers (ii) condensation polymer, (iii) copolymer.
Answer:
(i) Polythene, PVC
(ii) Buna – S, Buna – N
(iii) Nylon 6, Nylon 6, 6

Question 48.
Write the names of the structure of monomers of the following polymers, (i) Buna – S, (ii) Neoprene.
Answer:

Question 49.
What is the repeating unit in the condensation polymer by combining HOOC—CH₂—CFE —COOH (succinic acid) and H₂NCH₂CH₂NH₂ (ethylenediamine).
Answer:

Question 50.
Differentiate between molecular structure and behavior of thermoplastic and thermosetting plastic. Give one example of each type.
Answer:

Question 51.
What are the monomeric repeating units of Nylon 6, Nylon 6, 6?
Answer:
The monomeric repeating unit of nylon 6 is  which is derived from caprolactam.
The monomer repeating unit of nylon 6, 6 is derived from two monomers hexamethylenetetramine and adipic acid.

Question 52.
Name a synthetic polymer that is an amide.
Answer:
Nylon 6, 6.

Question 53.
Mention which of the following are addition polymers, (i) Terelene, (ii) Nylon 6, 6 (iii) Neoprene, (iv) Teflon.
Answer:
Neoprene and teflon are addition polymers.

Question 54.
What are biodegradable polymers?
Answer:
Polymers that disintegrate by themselves in biological systems during & certain period of time by oxidation are called biodegradable polymers, eg: PHBV. i.e., poly-β- hydroxybutyrate – co-β hydroxy valerate.

Question 55.
How are polymer classification based on forces operating between their molecule?
Answer:
Classification based as sources:

1. Natural polymer: Polymers are found in nature, mostly in plants, and animals are called natural polymers, eg: proteins and natural rubber, cellulose, silk.
2. Synthetic polymers: These are man-made polymers prepared in the laboratory, eg: polythene, PVC, teflon, nylon etc.
3. Semi-synthetic polymers: Polymers which are obtained by making some modifications in natural polymer by artificial means, eg: Nitrocellulose, cellulose diacetate, viscose rayon etc.

Question 56.
Give the preparation of bakelite and its uses.
Answer:
Preparation of bakelite:
Monomer: Phenol and formaldehyde
Type of polymerization: Condensation polymerization.

Uses: Navolac is used in paints. Soft bakelites are used for making glue for binding laminated wooden planks and in vanishes, Hard bakelites are used to prepare combs, pens etc…

Question 57.
Give the preparation and use of melamine.
Answer:
Preparation of melamine:
Monomer: Melamine and formaldehyde
Type of polymerisation: Condensation polymerisation


Uses: It is used for making unbreakable crockery.

Question 58.
Give examples for biodegradable polymer.
Answer:

1. Polyhydroxy butyrate (PHB)
2. Polyhydroxy butyrate-co-A-hydroxyl valerate (PHBV)
3. Polyglycolic acid (PGA), Polylactic acid (PLA)
4. Poly (∈ caprolactone) (PCL)

Question 59.
How is decron obtained from ethylene glycol and terephthalic acid?
Answer:
Decron is obtained by condensation polymerisation of ethylene glycol and terephthalic acid. The reaction is carried out at 420 – 460 K in the presence of a catalyst consisting of a mixture of zinc acetate and antimony trioxide.

Question 60.
How is urea-formaldehyde prepared?
Answer:
It is formed by the condensation polymerization of the monomers urea and formaldehyde.

Question 61.
How is PHBV prepared? Give equation mention its uses.
Answer:
It is the co-polymer of the monomers 3-hydroxybutyric acid and 3-hydroxypentanoic acid. In PHBV, the monomer units are joined by ester linkages.

Question 62.
Identify the type of polymer where A and B are monomers.
—A—B—B—A—A—A— B—A.
Answer:
Co-polymer.

Question 63.
Why is bakelite a thermosetting polymer?
Answer:
Due to high degree of cross linking, bakelite cannot be reshaped on heating and hence, bakelite is a thermosetting polymer.

Question 64.
Give a brief account of vulcanization of rubber.
Answer:
Vulcanization is heating natural rubber with sulphur and an appropriate additive to improve its physical properties. On vulcanization sulfur forms cross-links at the reactive sites of the double bond and thus rubber gets stiffened.

In this process, cross-linking of cis 1,4 polyisoprene chains through disulfide (—S—S) bond occurs.

Question 65.
Describe the preparation of neoprene and mention its uses.
Answer:
Neoprene is formed by the free radical polymerization of the monomer, 2-chloro buta-1,3 diene(chloroprene).

It is used is the manufacture of chemical containers and conveyor belts.

Question 66.
What is the name of the polymer formed from the monomers acrylonitrile and butal, 3-diene? How it is prepared?
Answer:
Buna – N is a copolymer formed by the polymerization of acrylonitrile and butal, 3-diene.

Question 67.
What type of polymer Buna-S is? Give its method of preparation.
Answer:
Preparation of Buna-S:
It is a copolymer. It is obtained by the polymerization of buta-1,3-diene and styrene in the ratio 3:1 in the presence of sodium.

Question 68.
Name the polymer formed by the copolymerization of glycine and aminocaproic acid. How it is prepared?
Answer:
Nylon 2 – Nylon 6.
Preparation: By condensation polymerization of the monomers glycine and aminocaproic acid.

Choose the correct answer:

1. Which one of the following antacids is an antihistamine?
(a) Ranitidine
(b) Lansoprazole
(c) Terfen adine
(d) Luminal
Answer:
(a)

2. Which of the following is / are nurologically active drug?
(a) Aspirin
(b) Phenelzine
(c) Heroin
(d) all the above
Answer:
(d)

3. Antiseptic chloroxylenol is:
(a) 4 – chloro, 3, 5 dimethyl phenol
(b) 3 – chloro, 4, 5 dimethyl phenol
(c) 4 – chloro, 2, 5 dimethyl phenol
(d) 5 – chloro, 3, 4 dimethyl phenol
Answer:
(a)

4. Structurally a biodegradable detergent should contain a:
(a) normal alkyl chain
(b) branched alkyl chain
(c) phenyl side chain
(d) cyclohexyl side chain
Answer:
(a)

5. Which of the following statements is not correct?
(a) Some antiseptics can be added to soap.
(b) Dilute solutions of disinfectants can be used as antiseptic.
(c) Disinfectants are antimicrobial drugs.
(d) Antiseptic medicine can be infected.
Answer:
(d)

6. The most useful classification of drugs for medicinal chemists is:
(a) on the basis of chemical structure
(b) on the basis of drug action
(c) on the basis of molecular targets
(d) on the basis of active drug.
Answer:
(c)

7. A compound that causes general anti¬depressant action on the central nervous system belongs to the class of:
(a) analgesics
(b) tranquilizers
(c) narcotic analgesics
(d) antihistamines
Answer:
(b)

8. Compound which is added to soap to inpart antiseptic properties is:
(a) sodium lauryl sulphate
(b) sodium do decyl benzene sulphonate
(c) resin
(d) bithional
Answer:
(d)

9. Glycerol is added to soap. Its function is:
(a) as a filler
(b) to increase lathering
(c) to prevent rapid drying
(d) to make soap granules
Answer:
(c)

10. Polyethylene glycols are used in the preparation of which type of detergents?
(a) Cationic detergents
(b) Anionic detergents
(c) Non-ionic detergents
(d) Soaps
Answer:
(c)

11. Which of the following is employed as anti-histamine?
(a) Omeprazole
(b) Chloroampinicol
(c) Diphenylhydramine
(d) Norethindrone
Answer:
(c)

12. Tincture of iodine is:
(a) aqueous solution of I₂
(b) solution of I₂ in KI
(c) alcoholic solution of I₂
(d) aqueous solution of KI
Answer:
(c)

13. Which among the following is not an antibiotic?
(a) Penicillin
(b) Oxytocin
(c) Erythromycin
(d) Tetracyclin
Answer:
(b)

14. Match entries in column I with appropriate entries in column II.


Answer:
(c)

15. Which of the following is not an antimicrobial?
(a) Salvarsan
(b) Sulphanilamide
(c) Prontsil
(d) Paracetamol
Answer:
(d)

16. Which of the following is not a semi synthetic polymer?
(a) Cis poly isoprene
(b) Cellulose nitrate
(c) Cellulose acetate
(d) Vulcanised rubber
Answer:
(a)

17. Which of the following polymers is prepared by condensation polymerisation?
(a) Styrene
(b) Nylon 6,6
(c) Teflon
(d) Rubber
Answer:
(b)

18. Which of the following is a chain growth polymer?
(a) Starch
(b) Nucleic acid
(c) Polystyrene
(d) Proteins
Answer:
(c)

19. Terelene is a condensation polymer of ethylene glycol and :
(a) benzoic acid
(b) pthalic acid
(c) salicylic acid
(d) terepthalic acid
Answer:
(d)

20. Which one of the following is a copolymer formed by condensation polymerisation?
(a) Terelene
(b) Buna – S
(c) Buna – N
(d) Neoprene
Answer:
(a)

21. Bakelite is obtained from phenol by the reaction with:
(a) HCHO
(b) (CH₂OH)₂
(c) CH₃CHO
(d) CH₃COCH₃
Answer:
(a)

22. Which of the following statements is not true?
(a) B una – S is a copolymer of butadiene and styrene.
(b) Natural rubber is a 1,4-polymer of isoprene.
(c) In vulcanisation the formation of sulphur bridges between different chains makes rubber harder and stronger.
(d) Natural rubber has trans configuration at every double bond.
Answer:
(d)

23. Teflon, styron and neoprene are all:
(a) copolymers
(b) condensation polymers
(c) homo polymers
(d) monomers
Answer:
(c)

24. Which of the following sets contain only thermoplastics?
(a) Polythene, bakelite, nylon-6
(b) Glyptal, melane, PAN
(c) PVC, PMMA, Polystyrene
(d) Polypropylene urea formaldehyde, teflon
Answer:
(c)

25. Which of the following sets contain only co-polymers?
(a) SBR, Glyptal, Nylon 6,6
(b) Nylon 6, Butyl rubber, Neoprene
(c) Poly ethylene, polyester, PVC
(d) Melmac, Bakelite, Teflon.
Answer:
(a)

26. Which of the following are not thermosetting polymers?
(1) Bakelite
(2) Polystyrene
(3) PVC
(4) Melmac
(a) 1, 2
(b) 2,3
(c) 2, 4
(d) 3, 4
Answer:
(b)

Students get through the TN Board 12th Chemistry Important Questions Chapter 14 Biomolecules which is useful for their exam preparation.

TN State Board 12th Chemistry Important Questions Chapter 14 Biomolecules

Question 1.
What are monosaccharides?
Answer:
Monosaccharides are carbohydrates which cannot be hydrolysed to simple molecules. Their general molecular formula is C_n(H₂O)_n where n = 3 to 7. There are two types. Those which contain an aldehyde group are called aldoses and those which contain a ketonic group are called ketoses. They are further classified as trioses, tetroses, pentose, hexoses etc according to as they contain 3, 4, 5, 6 carbon atom respectively.

Question 2.
Classify the following as monosaccharides and disaccharides:
Ribose: 2 – deoxy ribose; maltose, galactose, fructose, and lactose.
Answer:
Monosaccharides: Ribose, 2-Deoxyribose, galactose and fructose.
Disaccharides: Maltose and lactose.

Question 3.
What are the products of hydrolysis of (i) sucrose (ii) lactose.
Answer:
Both sucrose and lactoses are disaccharides. Sucrose on hydrolysis gives one molecule of each of glucose and fructose.

Lactose on hydrolysis gives one molecule of glucose and galactose.

Question 4.
How do you explain the presence of all six carbon atoms in glucose in a straight chain?
Answer:

Since, n – hexane has six carbon atoms connected in a straight chain, therefore glucose also has six carbon atoms connected in a straight chain.

Question 5.
The letter ‘D’ or ‘L’ before the name of a stereo isomer indicates the correlation of configuration of that particular stereo isomers. This refers to their relationship with one of the isomers of glyceraldehyde. Predict whether the compound is has D or L configuration.
Answer:

Since the configuration of the ‘OH’ group at the penultimate chiral carbon (last but one or C₅) is towards left, therefore the given compound has ‘L’ configuration.

Question 6.
How do you explain the presence of five – OH groups in a glucose molecule?
Answer:
On acetylation with acetic anhydride in presence of pyridine, or a few drops of cone. H₂SO₄, it is converted into glucose penta acetate.

This confirms the presence of five OH groups.

Question 7.
Why does compound (A) given below does not form an oxime?

Answer:
Glucose penta acetate does not have a free OH group at carbon atom 1(C₁) and hence cannot be converted into the open chain form having a free CHO group therefore, glucose penta acetate does not form an oxime.

Question 8.
How do you explain the presence of an aldehyde group in glucose molecule?
Answer:
Glucose reacts with hydroxyl amine, (NH₂OH) to form an oxime, and adds one molecule of hydrogen cyanide (HCN) to give a cyano hydrin. Therefore, glucose contains a carbonyl group which can be either an aldehyde or ketone. On mild oxidation with bromine water, it gives a carboxylic acid i.e., gluconic acid containing same six carbon atoms present in glucose. This indicates that the carbonyl group present in glucose is an aldehyde group.

Question 9.
How do you distinguish 1° and 2° alcoholic groups present in glucose? Explains with reactions.
Answer:
Consider the structure of glucose

The ‘OH’ group present on the terminal carbon (C₆) is called the primary alcoholic group while all other four ‘OH’ groups present in C₂, C₃, C₄ and C₅ are called secondary alcoholic groups. 1° alcoholic groups are readily oxidised to carboxylic acids but 2° alcoholic groups undergo oxidation under drastic conditions. For example glucose on oxidation cone. HNO₃ gives a dicarboxylic acid, saccharic acid, having the same number of carbon atoms as in glucose. This indicates that glucose contains one 1° alcoholic group while the remaining four are 2° alcoholic groups.

Question 10.
Write the reactions of D glucose which can’t be explained by its open chain structure. Reactions of D- glucose which can’t be explained by its open chain structure.
Answer:
(i) Glucose does not form NaHSO₃ additions product, aldehyde-ammonia, 2-4 DNP derivative and does not respond to schiff reagent test. These are the characteristic reactions of aldehyde.
(ii) Glucose reacts with NH₂OH to form an oxime but glucose penta acetate does not. This shows that the aldehyde group is absent in glucose penta acetate.
(iii) D(+) glucose exists in two isomeric forms i.e., α glucose and β glucose. Both these undergo mutarotation.
(iv) D(+) glucose forms two isomeric methyl glycosides. (Aldehydes normally react with two moles of methanol per mole of aldehyde where as one mole of glucose reacts with one mole of methanol to form a mixture of two methyl D – glucosides)

The two methyl glucosides behave as acetates.

Question 11.
Write the cyclic structure of glucose.
Answer:
The cyclic structures of a -D glucose and β -D glucose are as follows:

Question 12.
What is the structure feature characterising reducing sugars?
Answer:
The main structural feature of reducing sugars is the presence of an aldehyde group (— CHO) such as in glucose, mannose, galactose or a ketol group (—CO—CH₂OH) as present in fructose.

Question 13.
Fructose contains a keto group but it still reduces Tollen’s reagent. Explain.
Answer:
Under basic conditions of Tollen’s reagent fructose undergoes a rearrangement as shown below:

The same equilibrium is obtained even of one strands with D(+) mannose or D(-) fructose, i.e., Fructose gives an equilibrium mixture of fructose, glucose and mannose. Since both glucose and mannose contain —CHO group, they reduce Tollen’s reagent.

Question 14.
Explain the term glycosidic linkage with an example.
Answer:
The ethereal or oxygen linkage through two monosaccharides are joined together by the loss of a molecule of water to form a molecule of a disaccharide is called a glycosidic linkage. The glycosidic linkage of two α – D glucose in maltose is given below:

Question 15.
What happens when D – glucose is treated with the following reagents (i) HI (ii) Bromine water (iii) HNO₃.
Answer:

Question 16.
Glucose and fructose give the same osazone. Give reason.
Answer:

During osazone formation the reaction occurs only at C₁ and C₂. As glucose and fructose differ from each other only in the arrangement of atoms C₁ and C₂ they give the same osazones.

Question 17.
Name two components of starch. How do they differ from each other structurally?
Answer:
Starch is a polymer of a – glucose and consists of two components amylose and amylopectin. Amylose is a long unbranched chain with 200 – 1000 a D(+) glucose units held by C₁ – C₄ glycosidic linkage.
Amylopectin is a branched chain polymer of a D glucose units in which chain is formed by C₁ – C₄ glycosidic linkage branching occurs by C₁ – C₆ glycosidic linkage.

Question 18.
Name the reaction which proves the presence of carbonyl group in fructose.
Answer:
Fructose reacts with hydroxylamine (NH₂OH) and hydrogen cyanide (HCN). These reactions . prove the presence of carbonyl group in fructose.

Question 19.
Explain the reaction which indicates the presence of a carbonyl group in fructose.
Answer:
Partial reduction of fructose with sodium amalgam and water produces mixtures of sorbitol and mannitol which are epimers at second carbon. New asymmetric carbon is formed at C₂. This confirms the presence of keto group.

Question 20.
Oxidation of fructose with nitric acid gives glycolic acid and tartaric acid. What information that this reaction gives to establish the structure of fructose.
Answer:
On oxidation with nitric acid, it gives glycolic acid and tartaric acids which contain smaller number of carbon atoms than in fructose.

This shows that a keto group is present in C₂. It also shows the presence of 1° alcoholic groups at C₁ and C₆.

Question 21.
Explain why sucrose is called ‘invert’ sugar.
Answer:
Sucrose (+ 66.6°) and glucose (+ 52.5°) are dextrorotatory compounds while fructose is levo rotatory (- 92.4°). During hydrolysis of sucrose the optical rotation of the reaction,mixture changes from dextro to levo. Hence, sucrose is also called as invert sugar.

Question 22.
Write the open chain structure of D(+) fructose and indicate the asymmetric carbon atoms present in it.
Answer:

Question 23.
Briefly discuss the cyclic structure of fructose.
Answer:

Like glucose, fructose also forms cyclic form. Unlike glucose it forms a five membered ring similar to furan. Hence it is called furanose form. When fructose is a component of a saccharide as in sucrose, it usually occurs in furanose form.

Question 24.
Explain why sucrose is called a non reducing sugar.
Answer:
In sucrose, C₁ of α-D-glucose is joined to C₂ of -D-fructose. The glycosidic bond thus formed is called α-1,2 glycosidic bond. Since, the both the carbonyl carbons (reducing groups) are involved in the glycosidic bonding, sucrose is a non-reducing sugar.

Question 25.
Based on its cyclic structure, explain why lactose is a reducing sugar.
Answer:
On hydrolysis, it yields galactose and glucose. Here, the β-D-galactose and β-D-glucose are linked by β -1,4 glycosidic bond as shown in the figure. The aldehyde carbon is not involved in the glycosidic bondbence; it retains its reducing property and is called a reducing sugar.

Question 26.
Maltose is a reducing sugar. Explain.
Answer:
Maltose consists two molecules of α-D-glucose units linked by an α -1,4 glycosidic bond between anomeric carbon of one unit and C-4 of the other unit. Since one of the glucose has the carbonyl group intact it is also acts as a reducing sugar.

Question 27.
Mention the uses of cellulose.
Answer:
Cellulose is used extensively in manufacturing paper, cellulose fibres, rayon, explosive, (Gun cotton – Nitrated ester of cellulose) and so on. Humans cannot use cellulose as food because our digestive systems do not contain the necessary enzymes (glycosidases or cellulases) that can hydrolyse the cellulose.

Question 28.
Briefly explain the structure of cellulose.
Answer:
Cellulose is a straight chain polysaccharide.
The glucose molecules are linked by β(1, 4) glycosidic bond.

Question 29.
Following two amino acids lysine and glutamine dipeptide linkage. What are the two possible dipeptides?
Answer:

Question 30.
Give the. important uses of carbohydrates.
Answer:

1. Carbohydrates, widely distributed in plants and animals, acts mainly as energy sources and structural polymers.
2. Carbohydrate is stored in the body as glycogen and in plant as starch.
3. Carbohydrates such as cellulose which is the primary component of the plant cell wall is used to make paper, furniture (wood) and cloths (cotton).
4. Simple sugar glucose serves as an instant source of energy.
5. Ribose sugars are one of the components of nucleic acids.
6. Modified carbohydrates such as hyaluronate (glycosaminoglycans) act as shock absorber and lubricant.

Question 31.
What is glycogen? How is it different from starch?
Answer:
Glycogen is a carbohydrates stored in animal body. Starch is a mixture of two components a water soluble compounds called amylose (15 – 20%) and water insoluble amylopectin
(80 – 85%) chemically, amylose is a long unbranched chain with 200 – 1000 a – D (+) glucose units held by C₁ – C₄ glycosidic linkage. But both glycogen and amylopectin are branched polymers of α – D glucose rather glucogen is more highly branched than amylopectin. Whereas amylopectin chain consist of 20 – 25 glucose units glucose chain consists of 10 – 14 glucose units.

Question 32.
What is the basic structural difference between starch and cellulose?
Answer:
Starch contains amylose and amylopectin. Amylose is a linear polymer of α D glucose whereas cellulose is a linear polymer of β – D – glucose. In amylose, C-1 of one glucose unit is connected to C-4 of the other through glycosidic linkage.
Cellulose is a straight chain polysaccharides composed of only β -D glucose units which are joined by glycosidic linkages between C-1 of one glucose unit and C-4 of the next glucose unit.

Question 33.
What are essential and non essential amino acids? Give two examples of each type.
Answer:
α – amino acids which are required for health and growth of human beings but are not synthesised by the human body are known as essential amino acids, eg: valine, leucine, phenylalanine etc.,
On the other hand, α amino acids which are needed for health and growth of human being and are synthesised by the body are called non essential amino acids, eg: glycine, alanine, aspartic acid etc.

Question 34.
Give examples for fibrous and globular proteins.
Answer:
Fibrous protein: Keratin in skin, hair, nails, and wood, collagen in tendous. Fibroin in silk, myosin in muscles.
Globular protein: All enzymes, hormones like insulin, from pancreas, thyroglobulin from thyroid gland antibodies, haemoglobin.

Question 35.
What is isoelectic point? Explain with a suitable examples.
Answer:
The pH at which there is no net migration of the amino acid under the influence of an applied electrified is called isoelectric point.

Question 36.
What is peptide bond?
Answer:
The covalent bond —NH—CO— formed between —NH₂ group of one amino acid and —COOH group of the other with the elimination of a molecule of water is called a peptide bond.

Question 37.
How are epimers differ from anomers?
Answer:
Carbohydrates which differ in configuration at the glycosidic carbon (i.e., C₁ in aldoses and C₂ in ketoses) are called anomers while those differ in configuration at any carbon other than glycosidic carbon are called epimers.
For example α – D glucose and β-D glucose are anomers since they differ in configuration at C₁ while glucose and mannose are called epimers since they differ in configuration at C₂ (other than glycosidic carbon C₁). In other words glucose and mannose are C₂ epimers. Similarly glucose and galactose are C₄ epimers.

Question 38.
Differentiate between globular and fibrous proteins.
Answer:

Question 39.
Describe (i) primary structure (ii) secondary structure (iii) tertiary structure (iv) quaternary structure of proteins.
Answer:
(i) Primary structure: Proteins may contain one or more polypeptide chains. Each polypeptide chain has a large number of α – amino acids which are linked to one another in a specific sequence. The specific sequence in which the various α – amino acids present in a protein are linked to one another is called its primary structure. Any change in the sequence of α – amino acids creates a different protein.
(ii) Secondary structure: It refers to shape in which a long polypeptide chain exists. A protein may assume a – helix structure or β – pleated structure. The α – helix structure results due to regular coiling of polypeptide chain which is stabilized by intramolecular hydrogen bonding. In β pleated sheet structure, all peptide chains are stretched to a nearly maximum extention and then arranged side by side and held together by intramolecular hydrogen bonding.
(iii) Tertiary structure: The tertiary structure of proteins represent overall folding of the polypeptide chains, i.e., further folding of the secondary structure. The main force which stabilises 2° and 3° of proteins are hydrogen bonds, disulphide linkages, Vanderwaals forces of attraction and electrostatic force of attraction.
(iv) Quaternary structure: Same of the proteins are composed of two or more polypeptide chains referred to as sub-units. The spatial arrangement of these sub units with respect to each other is called quaternary structure.

Question 40.
What are the common types of secondary structure of protein?
Answer:
The conformations which the polypepetide chains assume as a result of hydrogen bonding is called the secondary structure of protein. The two types are

1. α helix and
2. β pleated structure

Question 41.
What types of bonding helps in stabilising α – helix structure of proteins?
Answer:
The α helix structure of proteins is stabilised by intramolecular hydrogen bonding between
C = O of one amino acid residue and —N—H of the fourth amino acid residue in the chain.

Question 42.
What is the effect of denaturation on the structure of proteins?
Answer:
During denaturation, 2° and 3° structures of proteins are destroyed but 1° structure remains intact. As a result of denaturation, the globular protein (soluble in H₂O) are converted to fibrous proteins (insoluble in H₂O) and their biological activity is lost.

Question 43.
Mention the causes for the denaturation of proteins.
Answer:
The denaturation of proteins occurs when the protein is exposed to the higher temperature the presence of certain such as urea, alteration of pH, ionic strength etc.

Question 44.
Mention the importance of protein.
Answer:

1. All biochemical reactions that occur in the living systems are catalysed by the catalytic proteins called enzymes.
2. Proteins such as keratin, collagen acts as structural backbones.
3. Proteins are used for transporting molecules (Haemoglobin), organelles (Kinesins) in the cell and control the movement of molecules in and out of the cells (Transporters).
4. Antibodies help the body to fight various diseases.
5. Proteins are used as messengers to coordinate many functions. Insulin and glucagon control the glucose level in the blood.
6. Proteins act as receptors that detect the presence of certain signal molecules and activate the proper response.
7. Proteins are also used to store metals such as iron (Ferritin) etc.

Question 45.
What are enzymes? What is the most important reason for their specific action?
Answer:
Enzymes are biomolecules & which catalyst biological reactions. Chemically they are globular proteins (water-soluble) that have very high molecular near ranging from 15,000 to 1,000,000 mol^-1.
Enzymes are highly specific in their actions. The specificity is due to the presence of active sites of definite size and shape on their surfaces so that only specific substrates can fit into them. This specific binding leads to the formation of enzyme substrates complex which accounts for high specificity.

Question 46.
Name the enzyme that converts (i) carbonic acid to CO₂ and H₂O (ii) hydrolysis of sucrose to fructose and glucose. (iii) hydrolysis of lactose to glucose and galactose.
Answer:
(i) Carbonic anhydrase enzyme catalyses the interconversion of carbonic acid to water and carbon dioxide.
(ii) Sucrose enzyme catalyses the hydrolysis of sucrose to fructose and glucose.
(iii) Lactase enzyme hydrolysis the lactose to glucose and galactose.

Question 47.
Explain the mechanism of enzyme action.
Answer:
Mechanism of Enzymatic action: The general scheme is represented as
Step 1: Binding of the enzyme (E) to the substrate (S) to form a complex (ES) is Enzyme – substrate complex.

Step 2: Product formation in the complex

Step 3: Release of enzyme product complex and leaving the enzyme as unchanged.

Question 48.
What are lipids? How are they classified?
Answer:
Lipids are the principal components of cell membranes including cell walls. They act as an energy source for living systems. Classification of lipids: Based on their structures Lipids can be classified as simple lipids, compounds lipids and derived lipids. Simple lipids can be further classified into fats, which are esters of long-chain fatty acids with glycerol (triglycerides) and waxes which are the esters of fatty acids with long-chain monohydric alcohols (Beeswax). Compounds lipids are the esters of simple fatty acid with glycerol which contain additional groups. Based on the groups attached, they are further classified into phospholipids, glycolipids and lipoproteins. Phospholipids contain a phospho-ester linkage while the glycolipids contain a sugar molecule attached. The lipoproteins are complexes of lipid with proteins.

Question 49.
How are vitamins classified?
Answer:
Vitamins are classified depending on their solubility in water.

1. Water-soluble Vitamins: These include Vitamin B – complex (B₁, B₂, B₅, i.e., nicotinic acid, B₅, B₁₂ and vitamin C)
2. Water-insoluble Vitamins (or fat-soluble Vitamins): These include Vitamins D, A, E and K. They are stored in the liver and in fat-storing tissues.

Question 50.
What are coenzymes and prosthetic groups?
Answer:
coenzymes are loosely held to the protein and can be easily separated by dialysis.
Prothetic group: These are tightly held to the protein molecule by covalent bonds. They can be separated only by hydrolysis.

Question 51.
What are nucleic acids? Mention their two important functions?
Answer:
Nucleic acids are polynucleotides i.e., they are formed by the condensation of thousand molecules of nucleotides with the elimination of water molecules.
Nucleic acids are of two types: deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). The two main functions of nucleic acids are:

1. DNA is responsible for the transmission of heredity effects from one generation to another. This is due to the unique property of replication during cell division as a result of which two identical DNA strands are transmitted to daughter cells.
2. DNA and RNA are responsible for protein synthesis needed for the growth and maintenance of our body. Actually, proteins are synthesised by various RNA molecules (rRNA, mRNA and tRNA) in the cell but the message for the synthesis of a particular protein is given by DNA molecules.

Question 52.
Write the structure of nucleic acids.
Answer:
Primary structure: The primary structure of nucleic acid refers to the sequence in which the four nitrogen bases (A, G, C and T in DNA or A, G, C and U in RNA) are attached to the sugar-phosphate backbone of a nucleotide chain.
Secondary structure: DNA consists of two strands of polynucleotides coiled around each other in form of a double helix. The backbone of each strand consists of sugar-phosphate units and the base unit of each strand are pointed into the interior of the helix and are linked together through hydrogen bonds. Whereas G and C are held by three H – bonds, A and T are held by H – bonds.

Question 53.
Write down the structure of sugar present in DNA.
Answer:
DNA contains β D – 2 deoxyribose as sugar. In structure in the furanose form is

Question 54.
What purine and pyrimidine bases are present in DNA and RNA?
Answer:
Purines: adenine and guanine Pyrimidine: Cytosine and thymine are present in DNA.
Cytosine and uracil is present in RNA.

Question 55.
What is a nucleoside?
Answer:
A nucleoside consists of two components, i.e., a nitrogenous base (purine or pyramidine)’ and a five-carbon sugar (ribose or deoxyribose). It is obtained when the nitrogenous base is attached, to C₁ of sugar by a β – linkage. Thus, in general, a nucleoside may be represented as a base – super. Examples of nucleosides are adenosine, cytidine etc.,

Question 56.
What is a nucleotide?
Answer:
A nucleotide consists of all the three basic components of nucleic acids, i.e., a nitrogenous purine or a pyrimidine base, a five-carbon ribose or deoxyribose and phosphoric acid. A nucleotide is obtained when a nitrogenous base is attached to C₁ of the sugar by a β linkage and a nucleotide is thus obtained when C₅—OH of the sugar is esterified with phosphoric acid. Thus, in general, nucleotides may be represented as a base – sugar-phosphate.

Question 57.
What type of linkage holds together the monomers of DNA?
Answer:
The monomers of DNA are polydeoxy ribo nucleotides. These are held together by H bonds. There are three H bonds between guanine and cytosine (G ≡ C) and two between adenine and thymine (A = T).

Question 58.
The two strands in DNA are not identical but complimentary explain.
Answer:
The two strands in the DNA molecule are held together through H — bonds between the purine base of one strand and pyrimidine base of the other and vice versa. Because of different sizes and geometries of the base, the only
possible pairing in DNA is G(guanine) and C(cytosine) through two hydrogen bonds i.e., bases (C ≡ G) and between A(adenine) and thymine (T) through two hydrogen bonds (i.e., A = T) due to this base – pairing principle the sequences of bases in one strand automatically fixes the sequence of bases in the other strand. Thus the two strands are not identical but complementary.

Question 59.
Mention the functional difference DNA and RNA.
Answer:

Question 60.
What is DNA fingerprinting? Explain.
Answer:
The DNA fingerprint is unique for every person. By using this method, individual-specific variation in human DNA can be detected.

Question 61.
When RNA is hydrolysed, there is no relationship among the quantities of different bases obtained. What does it suggest about the structure of RNA?
Answer:
A DNA molecule has two strands in which four complementary bases pair each other i.e., cytosine (C) always pairs with guanine (G) while Thymine (T) always pair with adenine(A). Therefore when a DNA molecule is hydrolysed, the molar amount of cytosine is equal to that of guanine and that of adenine is always equal to that of thymine. Since RNA has no such relationship between the quantities of the four bases (C, G, A and U) obtained, therefore, based on the base-pairing principle, i.e., A pairs with U and C pairs with G is not followed. Therefore, unlike DNA, RNA has a single strand.

Choose the correct answer:

1. Glucose does not react with:
(a) Br₂ / H₂O
(b) NH₂ OH
(c) (CH₃ CO)₂O
(d) NaHSO₃
Answer:
(d)

2. The letter ‘D’ in D – glucose signifies:
(a) Configuration at all chiral carbons
(b) Dextro rotatory
(c) That it is a monosaccharide
(d) Configuration at the penultimate chiral carbon.
Answer:
(d)

3. The term anomer of glucose refers to:
(a) isomers of glucose that differ in configuration at carbon one and four (C-1 and C-4).
(b) a mixture of D – glucose and L – glucose
(c) enantiomers of glucose
(d) isomers of glucose that differ in configuration at C-1.
Answer:
(d)

4. The helical structure of proteins is stabilised by:
(a) dipeptide bonds
(b) hydrogen bonds
(c) ether bonds
(d) peptide bonds
Answer:
(b)

5. The vitamins absorbed from intestine along with fats are:
(a) A, D
(b) A, B
(c) A, C
(d) D, B
Answer:
(a)

6. The human body does not produce:
(a) enzymes
(b) DNA
(c) vitamins
(d) hormones
Answer:
(c)

7. Adenosine is an example of:
(a) nucleotide
(b) nucleoside
(c) purine base
(d) pyramidine base
Answer:
(b)

8. Which of the following statements is not true about glucose?
(a) It is aldohexose.
(b) On heating with HI it forms n-hexane
(c) It is present in furanose form
(d) It does not give 2-4 DNP test.
Answer:
(c)

9. Which of the following reactions of glucose can be explained only by its cyclic structure?
(a) Glucose forms Penta acetate
(b) Glucose reacts with hydroxylamine to form an oxime.
(c) Pentaacetate of glucose does not react with hydroxylamine.
(d) Glucose is oxidised by nitric acid to gluconic acid.
Answer:
(c)
Hint: Due to the absence of free ‘OH’ group at C₁ cyclic structure of glucose Penta acetate cannot revert to open-chain aldehyde form and hence cannot form Penta acetate.

10. Three cyclic structures of monosaccharides are given below, which are anomers?

(a) I and II
(b) II and III
(c) I and III
(d) III is anomer of I and II
Answer:
(a)
Hint: Structure (I and II) differ only in the position of OH at C₁ and hence anomers.

11. Each polypeptide in a protein has amino acids linked with each other in a specific sequence. This sequence of amino acids is said to be :
(a) primary structure of proteins
(b) secondary structure of proteins
(c) tertiary structure of proteins
(d) quaternary structure of proteins
Answer:
(a)

12. RNA and DNA contains four bases each which of the following bases is not present in RNA.
(a) Adenine
(b) Uracil
(c) Thymine
(d) Cytosine
Answer:
(c)

13. In fibrous proteins, polypeptide chains are held together by:
(I) Vander waals forces
(II) disulphide linkages
(III) electrostatic forces of attraction
(IV) hydrogen bonds
(a) I and II
(b) II and IV
(c) III and IV
(d) IV only
Answer:
(b)

14. Which of the following does not exhibit the phenomenon of muta rotation?
(a) (-) Fructose
(b) (+) sucrose
(c) (+) Lactose
(d) (+) Maltose
Answer:
(b)
Hint: Only monosaccharides i.e., (-) fructose and reducing disaccharides i.e., (+) lactose and (+) maltose show mutarotation. Since (+) sucrose is a non reducing sugar, it does not show mutarotation.

15. Which of the following statements is not true regarding (+) lactose?
(a) (+) lactose, C₁₂H₂₂O₁₁ contains 8 (—OH) groups.
(b) On hydrolysis, (+) lactose gives equal amounts of D(+) glucose and D(+) galactose.
(c) (+) Lactose is a β – glycoside formed by the union of a molecule of D(+) glucose and a molecule of D(+) galactose.
(d) (+) Lactose is a reducing sugar and does not exhibit mutarotation.
Answer:
(d)

16. The vitamin which is neither soluble in water nor in fat is:
(a) biotin
(b) phylloquinone
(c) thiamine
(d) ergocalciferol
Answer:
(a)

17. Which of the following is not a fat soluble vitamins?
(a) Vitamin B complex
(b) Vitamin D
(c) Vitamin E
(d) Vitamin A
Answer:
(a)

18. Which of the following structure represent the peptide chain?

Answer:
(c)

19. The tripeptide is written as glycine – alanine – glycine. The correct structure of the tripeptide is:

Answer:
(c)

20. The hormone which controls the processes of the burning of fats, proteins and carbohydrates and liberates energy in the body is:
(a) thyroxine
(b) adrenaline
(c) insulin
(d) cortisone
Answer:
(c)

21. The secondary structure of a protein refers to:
(a) fixed configuration of polypeptide backbone.
(b) a- helical backbone
(c) hydrophobic interactions
(d) sequence of amino acids
Answer:
(b)

22. Which of the following statements about “denaturation” given below are correct?
(i) denaturation of proteins causes loss of secondary and tertiary structure of proteins.
(ii) denaturation leads to the conversion of double strand DNA to a single strand.
(iii) denaturation affects the primary structure which gets distorted.
(a) (i) and (iii)
(b) (ii) and (iii)
(c) (i) and (ii)
(d) (i), (ii) and (iii)
Answer:
(c)

23. The pyramidine bases present in DNA are :
(a) Cytosine and adenine
(b) Cytosine and guanine
(c) Cytosine and thymine
(d) Cytosine and uracil
Answer:
(c)

24. Nitrogen base that is found in RNA but not in DNA is:
(a) uracil
(b) thymine
(cl cytosine
(d) adenine
Answer:
(a)

25. RNA and DNA are chiral molecules, then chirality is due to:
(a) D – sugar component
(b) L – sugar component
(c) Chiral bases
(d) Chiral phosphate ester unit
Answer:
(a)

26. In DNA, the complimentary bases are:
(a) Adenine and guanine; thymine and cytosine
(b) Uracil and adenine; cytosine and guanine
(c) Adenine and thymine; guanine and cytosine
(d) adenine and thymine; guanine and uracil
Answer:
(c)

27. Assertion: Fructose does not contain an aldehyde group but still reduces Tollen’s reagent.
Reason: In presence of base, fructose undergoes rearrangement to form glucose and mannose.
(a) Both assertion and reason are correct and the reason is a correct explanation of assertion.
(b) Both assertion and reason are correct but reason is not a correct explanation of assertion.
(c) Assertion is true but reason is false.
(d) Both assertion and reason are false.
Answer:
(a)

28. Assertion: Glycosides are hydrolysed in acidic conditions.
Reason: Glycosides are acetals.
(a) Both assertion and reason are correct and the reason is a correct explanation of assertion.
(b) Both assertion and reason are correct but reason is not a correct explanation of assertion.
(c) Assertion is true but reason is false.
(d) Both assertion and reason are false.
Answer:
(a)

29. Match the entries in column I with appropriate entries in column II and choose the correct option.

Answer:
(b)

30. The two forms of D – glucopyranose are called:
(a) Enantiomers
(b) Anomers
(c) Epimers
(d) Diastereomers
Answer:
(b)

Students get through the TN Board 12th Chemistry Important Questions Chapter 13 Organic Nitrogen Compounds which is useful for their exam preparation.

TN State Board 12th Chemistry Important Questions Chapter 13 Organic Nitrogen Compounds

Answer the following questions.

Question 1.
Classify the following aliphatic or aromatic nitro compounds.
(i) 1, 2, dimethyl-1-nitropropane
(ii) 2-nitro-1 -methyl benzene
(iii) 1, 3, 5 trinitro benzene
(iv) 2-phenyl-1-nitro ethane
(v) 2-methyl-2-nitro propane
Answer:

Question 2.
What are nitro compounds? How are they classified? Give one example for each type.
Answer:
(i) Nitro compounds are considered as the derivaties of hydrocarbons. If one of the hydrogen atom of hydrocarbon is replaced by the —NO₂ group, the resultant organic compound is called a nitrocompound.
(ii) Examples for primary nitro compound.

(iii) Example for secondary nitro compound.

(iv) Example for a tertiary nitro compound.

Question 3.
Write the structural formula of the isomers of the following compound and indicate the type of isomerism involved, (i) 1-nitrobutane,
(ii) nitroethane.
Answer:
(i) (a) 1-nitrobutane and 2-methyl-1-nitropropane are- chain isomers. These two isomers differ in the length of carbon chain and hence exhibit chain isomerism.

(b) 1-nitrobutane, 2-nitrobutane and 2-methyl 2-nitropropane are position isomers. They differ in the position of the functional group and hence exhibit positfon isomerism.

(c) 1-nitrobutane and butyl nitrite are functional isomers. They differ in the nature of the functional group and hence functional isomerism.

(ii) Nitromethane and methyl nitrite exhibit tautomerism.

Question 4.
Methyl nitrite and nitro methane exhibits tautomerism. How will you distinguish between these form?
Answer:

Question 5.
Between 2-nitrobenzene, and 2-methyl – 2- nitro propane which does not exhibit tautomerism? Why?
Answer:
Tautomerism is exhibited by nitro alkanes which contain one or more ‘α’ hydrogen atoms. Then 1° and 2° nitro alkanes exhibit tautomerism while 3° nitro alkanes which do not have a ‘α’ hydrogen atom does not exhibit tautomerism.
2-nitrobutane has a hydrogen atom and hence exhibit tautomerism. While 2-methyl -2- nitropropane does not contain an a hydrogen atom and hence does not exhibit tautomerism.

Question 6.
Explain the acidic nature of nitroalkanes.
Answer:
Primary and secondary nitro alkanes show acidic nature because of the presence of a hydrogen atom.
Because of the presence of electron withdrawing nitro group, the ‘α’ hydrogen atom is abstracted by a base.

Hence, they are acidic. When the number of alkyl groups attached to α- carbon acidity decreases because of +1 effect of alkyl groups.

Question 7.
How will you prepare nitro benzene from (i) ethyl bromide (ii) methane, (iii) α – chloroacetic acid (iv) tert-butyl amine, (v) acetaldoxine.
Answer:
(i) Alkyl bromides (or) iodides on heating with ethanolic solution of potassium nitrite gives nitroethane.

(ii) Gaseous mixture of methane and nitric acid passed through a red hot metal tube to give nitromethane.

(iii) α – chloroacetic acid when boiled with aqueous solution of sodium nitrite gives nitromethane.

(iv) tert-butyl amine is oxidised with aqueous KMnO₄ to give tert – nitro alkanes.

(v) Oxidation of acetaldoxime and acetoneoxime with trifluoroperoxy acetic acid gives nitroethane (1°) and 2- nitropropane (2°) respectively.

Question 8.
Give the equation for the reduction of nitromethane in (a) acid medium and (b) neutral medium.
Answer:
(a) Nitromethane on reduction in acid medium gives methylamine.

(b) Reduction under neutral condition using Zn / NH₄OH or Zn /CaCl₂, hydroxylamine is formed.

Question 9.
Complete the following equation. Identify A, B, and C.


Answer:

Question 10.
How does ethyl nitrite react with (i) Sn / HCl and (ii) HCl / H₂O.
Answer:

Question 11.
What is Nef carbonyl synthesis? Give equation.
Answer:
The formation of an aldehyde by the alkaline hydrolysis of a nitro alkane is known as Nef carbonyl synthesis.

Question 12.
How are the following conversion made?
(i) Benzene to mcta dinitro benzene, (ii) Nitro benzene to nitroso benzene, (iii) Nitro benzene to azo benzene, (iv) Nitro benzene to hydrazo benzene.
Answer:

Question 13.
Identify the reagents used in the following conversions. Write complete equations.
(i) nitrobenzene to aniline
(ii) metadinitrobenzene to metanitroaniline
(iii) nitrobenzene to 3-nitrobenzene sulphonic acid.
Answer:
(i) Any reducing agent: Ni (or) Pt or LiAlH₄

(ii) Ammonium poly sulphide

(iii) Conc. H₂SO₄

Question 14.
Explain why nitro group in nitro benzene is meta directing.
Answer:
The structure of nitro benzene is a resonance hybrid of the following cannonical structures.

As a result of electron withdrawing nature of the NO₂ group, the electron density at ortho and para position deefeases compafed to meta position i.e., the meta position is relatively electron rich compound to ortho and para positions. Hence the electrophile attacks the meta position.

Question 15.
How will you effect the following conversions?
(i) Benzene to m-chloro nitro benzene,
(ii) Benzene to 1, 2, 3 tri nitro benzene
(iii) m-chloro nitro benzenetto m-chloro aniline,
(iv) 1, 3, di nitrobenzene to 3- nitro aniline.
Answer:

Question 16.
Give the IUPAC names of the following:

Answer:
(i) N -phenyl benzenamine
(ii) N, N -diphenyl benzenamine
(iii) N -methyl-N-phenylethanamine
(iv) prop -2- en-1-amine
(v) hexane-1, 6-diamine
(vi) N -methyl-propan-1-amine
(vii) N, N -diethyl-butan-1-amine
(viii) N -ethyl- N-methyl propan-2-amine
(ix) N, N -dimethyl-benzenamine
(x) phenyl-methanamine

Question 17.
Write the structures of the chain isomers of Butan-1-amine.
Answer:

Question 18.
Explain ‘metamerism’ with a suitable example of amines.
Answer:
Aliphatic amines having the same molecular formula but different alkyl groups on either side of the nitrogen atoms show metamerism,
eg: CH₃CH₂NHCH₂CH₃ (diethyl amine) and CH₃NHCH₂CH₂CH₃ (methyl-n-propyl amine)
CH₃NHCH(CH₃₂)₂ (Isopropyl methylamine) are metamers.

Question 19.
What are all the possible isomers of an amine having the molecular formula C₃H₉N and C₄H₁₁N.
Answer:

These amines exhibit functional isomerism.
Amine (C₄H₁₁N): CH₃CH₂CH₂CH₂NH₂ (Butan-1-amine) exhibit chain as well as position isomerism.

Question 20.
Write the structure of the following:
(i) 4N-dimethyl pentan-2-amine
(ii) 2 (N, N-dimethyl) butanamine
(iii) 2-aminoethanol
(iv) 4-aminobutanoicacid
(v) N-methyl-2-nitro pentanamine
(vi) prop-2-en-l -amine.
(vii) N-ethyl-N-methylbenzenamine
(viii) 3-methylbenzenamine
(ix) 2-methoxybenzenamine
(x) N-phenylbenzenamine
Answer:

Question 21.
How is ethanamine prepared from (i) nitroethane, (ii) ethanenitrile, (iii) acetamide, (iv) ethyl bromide?
Answer:
(i) Reduction of nitroethane using H₂ in the presence of Ni or Sn/HCl or Pd/H₂.

(ii) Reduction of ethanenitrile using sodium amalgam in ethanol.

(iii) Reduction of acetamide using LiAlH₄.

(iv) By Gabriel’s phthalimide synthesis.

Question 22.
Identify the products:

Answer:
(i) C₆H₅NH₂ (aniline)
(ii) CH₃NHCH₃ (N-methyl methanamine)
(iii) C₆H₅NH₂ (aniline)
(iv) C₆H₅CH₂NH₂ (benzyl amine)

Question 23.
Using sodium azide (NaN₃) convert methyl bromide to methylamine.
Answer:

Question 24.
How will you prepare aniline from (i) chlorobenzene and (ii) phenol?
Answer:

Question 25.
What happens when
(i) Vapours of ethanol and ammonia are passed over alumina.
(ii) Ethanamide is treated with LiAlH₄. Give equation.
Answer:

Question 26.
Explain Why?
(i) Amines have higher boiling points than hydrocarbons of comparable molecular mass.
(ii) Among isomeric amines 3° amines have the lowest melting point.
(iii) The boiling point of amines are lower than those of alcohols and acids of comparable molecular mass.
(iv) Aliphatic amines with maximum six carbon atoms are soluble in water to some extent, while aromatic amines are insoluble in water.
Answer:
(i) This is due to the reason that amines being polar form inter molecular hydrogen bonding (except tertiary amines which do not have a H atom linked to N atom) and exist as associated molecules.

(ii) The degree of association depends on the extent of hydrogen bonding. Since 1° amines have two, 2° amines have one while 3° amines have no hydrogen linked to nitrogen. Therefore, among isomeric amine 1° amines have highest while 3° amine have the lowest boiling points.
(iii) The electronegativity of nitrogen is lower than oxygen, amines form weaker H—bonding compared to alcohol and carboxylic acids.i.e., The extent of association is less compared to that of alcohols or carboxylic acids. Hence amines will have lower boiling point compared to alcohol or carboxylic acid of comparable molecular mass.
(iv) All the three classes of amines (1°, 2° and 3°) form H bonds with water as a result lower aliphatic amines are soluble in water. As the size of the alkyl group increases (with increase in molecular mass), the solubility decreases due to a corresponding increase in hydrocarbon part of the molecule. The borderline solubility is reached with amines of about six carbon atoms in the molecule. Aromatic amines, on the other hand are insoluble in water. This is due to larger hydrocarbon part which tend to retard the formation of H-bonds.

Question 27.
Account for the fact that among ethyl amines, the decreasing order of basicity in aqueous solution is (CH₃CH₂)₂NH > (CH₃CH₂)₃N > CH₃CH₂NH₂.
Answer:
The basicity of an amine in aqueous solution primarily depends upon the stability of the ammonium cation or the conjugate acid formed by accepting a proton from water. The stability of the ammonium cation in turn depends on the combination of the following factors.
(i) +1 effect of alkyl groups.
(ii) Extent of hydrogen bonding with water molecules.
(iii) Steric effects of the alkyl groups.
In the case of alkyl groups bigger than ‘CH₃’ group i.e., ethyl, propyl, etc there will be steric hindrance to hydrogen bonding. As a result, stability due to +1 effect predominates over the stability due to H—bonding and hence 3° amines because more basic than 1° amines. In all overall decreasing basic strength of ethyl amine follows the sequence (CH₃CH₂)₂NH > (CH₃CH₂)₃N > CH₃CH₂NH₂ > NH₃.

Question 28.
How does nitrous acid (a mixture of sodium nitrite and dil. HCl) react with (i) CH₃NH₂ (ii) (CH₃)₂NH and (iii) (CH₃)₃N? Give equations.
Answer:
Aliphatic primary amines react with nitrous acid give an alcohol and nitrogen gas is produced. Methyl amine is an exception.

Secondary amines will form nitroso alkyl amine.

Tertiary amines react with nitrous acid and form nitrites.

Question 29.
How does nitrous acid react with the following? Give equations.
(i) ethylamine, (ii) di-ethylamine, (iii) triethyl amine, (iv) aniline, (v) N-methyl aniline, (vi) N, N- dimethylaniline.
Answer:
(i) Ethylamine reacts with nitrous acid to give ethyl diazonium chloride, which is unstable and it is converted to ethanol by liberating N₂.

(ii) A yellow dye of N-nitrosodiethylamine is formed.

(iii) Triethylammoniumnitrate which is soluble in water formed.

(iv) Aniline reacts with nitrous acid at low temperature (273 – 278 K) to give benzene diazonium chloride which is stable for a short time and slowly decomposes even at low temperatures.

This reaction is known as diazotisation.
(v)

This reaction is known as Libermann’s nitroso test.
(vi) Aromatic tertiary amine reacts with nitrous acid at 273K to give p-nitroso compound.

Question 30.
Explain why amino group is ortho para directing in electrophilic substitution reactions.
Answer:
The NH₂ group is a strong activating group. In aniline the NH₂ is directly attached to the benzene ring, the lone pair of electrons on the nitrogen is in conjugation with benzene ring which increases the electron density at ortho and para position, thereby facilitating the electrophilic attack at ortho and para.

Question 31.
Aniline gives 2, 4, 6 tribromo aniline when treated with bromine water, but not a mono bromo aniline. Explain why?
Answer:
Aniline is a more powerful activating group. The lone pair of electrons enters into conjugation with the benzene ring, as a result both ortho and para position become rich in electron density. At the same time Br⁺ is also a strong electrophile. Hence, all the three positions are attacked by the electrophile.

Question 32.
Why is it necessary to acetylate aniline to get a mono bromo aniline?
Answer:
Acetylation of aniline reduces the activity of the amino group. The activity of the acetylated amine is reduced because the lone pair of electron on nitrogen is delocalised by the neighbouring carbonyl group by resonance. Hence, it is not easily available for conjugation.

The acetyl amino group is less activating than amino group.

Question 33.
Explain why direct nitration of aniline gives a mixture of ortho, meta and para isomers.
Answer:

Nitration of aniline involves acidic medium. So protonation of aniline takes place forming mainly m-nitro aniline. Hence, direct nitration of aniline forms the following products.

Question 34.
How will you convert aniline?
(i) to p-bromo aniline
(ii) to 2,4,6 tribromo aniline
(iii) to para nitro aniline
(iv) to benzene diazonium chloride
(v) to sulphanilic acid
Answer:

Question 35.
What is zwitter ion? Explain with an example.
Answer:
Zwitter ion is a compound in which both acidic and basic groups are present in the same molecule, eg: sulphanilic acid. It has an acidic (SO₂OH) and a basic group (NH₂). Thus a proton from the acid leaves and protonates the basic group. As a result it exists as a dipolar ion.

Question 36.
How will you distinguish between primary, secondary and tertiary amine?
Answer:

Heisenberg reagent: Benzene sulphoanyl chloride in the presence of excess aqueous KOH solution.

Question 37.
Complete the following reactions:

Answer:

Question 38.
Give examples for (i) Sandmeyer’s reaction (ii) Gattermann reaction.
Answer:
(i) Sandmeyer’s reaction: Benzene diazonium chloride solution on reaction with cuprous chloride in hydrochloric acid (CuCl / HCl) or cuprous bromide in hydrochloric acid (CuBr / HCl) gives corresponding chloro benzene or bromo benzene. This reaction is known as Sandmeyer’s reaction. Aryl cyanides can also be prepared by this method.

(ii) Gattermann reaction: This reaction involves the treatment of benzene diazonium chloride with Cu / HCl or Cu / HBr respectively instead of cuprous halide and hydrogen halide.

Question 39.
How does the following reagents react with benzene diazonium chloride? Give equations.
(i) HBF₄ and the product formed is heated.
(ii) HBF₄ and die product formed is heated with an aqueous solution of sodium nitrite in the presence of copper.
(iii) HBF₄ and the product is heated with CH₃COOH.
(iv) Cuprous cyanide in the presence of KCN.
Answer:

Question 40.
Accomplish die following conversions.
(i) Nitrobenzene to benzene,
(ii) 4-Nitro aniline to 1, 2, 3 -tribromo benzene,
(iii) p-toludine to 2-bromo-4-methyl aniline,
(iv) m-nitro aniline to m-chloroaniline,
(v) p-nitroaniline to p-iodomtro benzene,
(vi) benzyl chloride to 2-phenyl ethanamine.
Answer:
(i) Nitrobenzene to benzene:

(ii) 4 -nitro aniline to 1, 2, 3 – tribromo benzene.

(iii) p-toludine to 2-bromo 4-methyl aniline.


(vi) Benzyl chloride to 2- phenyl ethylamine.

Question 41.
Give equations for the following reactions.
(i) Ethyl bromide is treated with KCN
(ii) Heating acetamide with P₂O₅
(iii) Heating acetaldoxime with P₂O₅
(iv) Treating methyl magnesium bromide with cyanogen chloride.
Answer:

Question 42.
Write the IUPAC names of the following:


Answer:

Question 43.
What is the reducing agent used in the following reduction reactions? Give equations.
(i) Ethanenitrile to ethanamine
(ii) Benzonitrile to benzylamine
(iii) Ethane nitrile to Acetaldimine hydrochloride which on hydrolysis gives acetaldehyde.
Answer:
(a) Complete reduction or strong reduction when reduced with H₂ in the presence of Pt or Ni as catalyst or by using LiAlH₄, or sodium and alcohol alkyl or aryl cyanides yield primary amines.

This specific type of reduction of alkyl or aryl cyanides using LiAlH₄ or Na/ alcohol is named as mendices reduction.
(b) Partial reduction or mild reduction: When SnCl₂ / HCl is used as a reducing agent at room temperature alkyl or aryl cyanides are reduced to amine hydrochloride which on subsequent hydrolysis gives aldehyde. This type of reduction is named as Stephen’s reduction.
SnCl₂ + 2HCl → SnCl₄ + 2 [H]

Question 44.
Give examples for (i) Thrope nitrile condensation and (ii) Levine and Hauser acetylation.
Answer:
(i) Thrope nitrile condensation: Self condensation of two molecules of alkyl nitrile (containing α—H atom) in the presence of sodium to form iminonitrile.

(ii) Levine and Hauser acetylation: The nitriles containing α-hydrogen also undergo condensation with esters in the presence of sodamide in ether to form ketonitriles. This reaction is known as “Levine and Hauser” acetylation. This reaction involves replacement of ethoxy (OC₂H₅) group by methylnitrile (-CH₂CN) group and is called as cyanomethylation reaction.

Question 45.
Write the electronic structure of alkyl cyanides and isocyanides.
Answer:
The electronic structure of alkyl cyanides is

The carbon atom of CN group is sp hybridised. CN group contain one σ and two pi bonds.
The electronic structure of isocyanides is

Structurally isocyanides are represented as a resonance hybrid of the following two forms.

The dipolar form (I) makes higher contribution.

Question 46.
Name the reagents used in the following reactions.

Answer:

Question 47.
What happens when methyl isocyanide is:
(a) treated with dilute HCl.
(b) treated with sodium and alcohol
(c) heated at 250°C
(d) treated with sulphur in the presence of ozone.
Answer:

Question 48.
Mention the uses of (a) Nitro alkanes,
(b) Nitrobenzene,
(c) Cyanides and isocyanides
Answer:
(a) Nitroalkanes:

1. Nitromethane is used as a fuel for cars.
2. Chloropicrin (CCl₃NO₂) is used as an insecticide.
3. Nitroethane is used as a fuel additive and precursor to explosive and they are good solvents for polymers, cellulose ester, synthetic rubber and dyes etc.,
4. 4% solution of ethylnitrite in alcohol is known as sweet spirit of nitre and in used as diuretic.

(b) Nitrobenzene:

1. Nitrobenzene is used to produce lubricating oils in motors and machinery.
2. It is used in the manufacture of dyes, drugs, pesticides, synthetic rubber, aniline and explosives like TNT, TNB.

(c) Cyanides and isocyanides;

1. Alkyl cyanides are important intermediates in the organic synthesis of larger number of compounds like acids, amides, esters, amines etc.
2. Nitriles are used in textile industry in the manufacture of nitrile rubber and also as a solvent particularly in perfume industry.

Question 49.
An organic compound (A) having the molecular formula C₂H₇N is treated with nitrous acid to give (B) of molecular formula C₂H₆O which answers the iodoform test. Identify A and B and explain the reactions.
Answer:

Since, ‘B’ is an alcohol formed from A by the action of nitrous acid, A should be a primary amine which contains ‘NH₂’ group.
C₂H₅N—NH₂=C₂H₅ i.e. The alkyl group is C₂H₅ and hence A is C₂H₅NH₂ ethyl amine. B is ethyl alcohol and it is confirmed by the fact that it answer iodo form test.

Question 50.
An organic compound (A) with molecular formula C₆H₇N gives (B) with HNO₂ / HCl at 273K. The aqueous solution of (B) on heating gives compound (C) which gives violet colour with neutral FeCl₃. Identify the compounds A, B and C. Write the equations.
Answer:
A = C₆H₅NH₂ (aniline);
B = C₆H₂N₂Cl (benzene diazonium chloride)
C = C₆H₅OH (phenol)

(i) Since ‘C’ gives a violet colouration with neutral FeCl₃ it should be phenol.
(ii) Since phenol is obtained by boiling aqueous solution of (B), it should be benzene diazonium chloride.
(iii) Hence, A should be aniline.
Equation:

Choose the correct answer:

1.1, 2 dimethyl- 1-nitropropane. Choose the
incorrect statement about this compound.
(a) It is a primary nitro compound.
(b) It is also called nitroneopentane.
(c) The ‘NO₂’ group is attached to a secondary carbon atom.
(d) It is an aliphatic compound.
Answer:
(c)

2. 1-nitrobutane and 2-methyl-1-nitro propane:
(a) chain isomers
(b) position isomers
(c) functional isomers
(d) metamers
Answer:
(a)
Hint:

3. Which of the following nitro compounds does not exhibit tautomerism?

Answer:
(d)
Hint: Tertiary nitro alkanes do not exhibit tautomerism due to absence of a-H atoms.

4. The incorrect statement between nitroform and acidform of nitromethane is:
(a) nitroform is less acidic whereas aciform is more acidic.
(b) nitroform dissolves in NaOH slowly while aciform dissolves in NaOH instantly.
(c) Both decolorise FeCl₃ solution
(d) They are tautomers
Answer:
(c)
Hint: Nitroform decolorises FeCl₃ solution while aciform gives a reddish brown colour with FeCl₃ solution.

5.

Identify A and B.
(a) A = CH₃CH₂NO₂ ; B = CH₃CH₂NH₂
(b) A- CH₃NO₂ ; B = CH₃NH₂
(c) A = CH₃CHO ; B = CH₃CH₂OH
(d) A = CH₃CH₂NH₂ ; B = CH₃CH₂OH
Answer:
(a)

6.

Identify A and B.


Answer:
(b)

7. The products obtained by the reduction of nitromethane in acid medium and neutral medium are:
(a) methylamine and N-methylhydroxylamine
(b) methylamine and ethanol
(c) N-methylhydroxylamine and methylamine
(d) N-methylhydroxylamine in both cases.
Answer:
(a)
Hint:

8. An amine is boiled with HCl and H₂O. Which of the following will give acetone:
(a) CH₃NH₂
(b) (CH₃)₂CHNO₂
(c) (CH₃)₃CNO₂
(d) both (b) and (c)
Answer:
(b)
Hint: CH₃NH₂ gives CH₃COOH (CH₃)₂
CHNO₂ gives (CH₃)₂CO
(CH₃)₃ CNO₂ no reaction

9. The correct IUPAC name for CH₂=CH—CH₂NH—CH₃ is:
(a) Allylmethyl amine
(b) 2-amino-4-pentane
(c) 4 amino pent-l-ene
(d) N-methyl prop-2 en-1 amine
Answer:
(d)

10. Amongst the following the strongest base in aqueous medium is:
(a) CH₃NH₂
(b) NC—CH₂NH₂
(c) (CH₃)₂NH
(d) C₆H₅NH—CH₃
Answer:
(c)
Hint: 2° amines are more basic than 1° amines, i. e., (CH₃)₂NH is more basic than CH₃NH₂. Due to -I effect of CN group NC—CH₂NH₂ is less basic than even CH₃NH₂. C₆H₅NHCH₃ is less basic than both C₆H₅NH₂ and (CH₃)₂NH due to delocalisation of lone pair of electrons on the N atom into the benzene ring.

11. In order to prepare a 1 ° amine from an alkyl halide with simultaneous addition of one CH₂ group in the carbon chain, the reagent used a source of nitrogen is:
(a) Sodium amide, NaNH₂
(b) Sodium azide, NaN₃
(c) Potassium cyanide, KCN
(d) Potassium phthalimide C₆H₄(CO₂) N^–K^–
Answer:
(c)
Hint: Cyanides on reduction gives 1: amines with a CH₂ group

12. The correct increasing order of basic strength for the following compounds is:

(a) II < III < I
(b) III < I < II
(c) III < II < I
(d) II < I < III
Answer:
(b)

13. Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms in the chain is:
(a) Hoffmann bromamide reaction
(b) Gabriel’s phthalimide synthesis
(c) Sandmeyer’s reaction
(d) Reaction with NH₃
Answer:
(b)

14. Which of the following compounds is the weakest Bronsted base?

Answer:
(c)
Hint: Amines (a) and (b) have a stronger tendency to accept a proton and hence stronger Bronsted bases than phenol (c) and alcohol (d) since phenol is more acidic than alcohol, phenol (c) has the least tendency to accept a proton and hence the weakest Bronsted base.

15. Which of the following compounds cannot be prepared by Sandmeyer’s reaction?
(I) Chlorobenzene
(II) Bromobenzene
(III) Iodo benzene
(IV) Fluoro benzene
(a) (IV)
(b) (III)
(c) (I) and (II)
(d) (III) and (IV)
Answer:
(a)

16. The products of the following reaction are:


Answer:
(c)
Hint: —NHCOCH₃ is an o/p directing group.

17. An organic compound ‘A’ on treatment with NH₃ gives ‘B’ which on heating gives ‘C’. ‘C’ when treated with Br₂ in the presence of KOH produces ethylamine. The compound ‘A’ is:

Answer:
(d)
Hint:

18. In a set of reactions, meta mono benzoic acid gave a product ‘D’. Identify D.



Answer:
(d)
Hint:

19.

Answer:
(b)
Hint: Diazonium salts of benzylamine is not stable. It decomposes insitu, to form benzyl alcohol.

20. Predict the product:


Answer:
(d)

21. Aniline in a set of following reactions yielded a coloured product Y. The structure of Y would be:

Answer:
(b)
Hint:

22. Butylamine (I), diethyl amine (II) and N, N diethyl amine, (III) have the same molar mass. The increasing order of their boiling points is:
(a) III < II < I
(b) I < II < III
(c) II < III < I
(d) III < I < II
Answer:
(a)
Hint: Extent of H-bonding increases as the number of H-atoms increases and hence boiling point increases in the order 3°<2°< 1°.

23. Assertion: Ammonolysis of alkyl halides is not a suitable method for the preparation of primary amines.
Reason: Ammonolysis of alkyl halides mainly produces 2° amines.
(a) Both assertion and reason are true and reason is the correct explanation of assertion.
(b) Both assertion and reason are true and reason is not the correct explanation of assertion.
(c) Assertion is true but reason is false.
(d) Both assertion and reason are false.
Answer:
(c)

24. Assertion: Gabriel phthalimide reaction can be used to prepare aryl and arylalkyl amines.
Reason: Aryl halides are as reactive as alkyl halides towards nucleophilic substitution reactions.
(a) Both assertion and reason are true and reason is the correct explanation of assertion.
(b) Both assertion and reason are true and reason is not the correct explanation of assertion.
(c) Assertion is true but reason is false.
(d) Both assertion and reason are false.
Answer:
(d)
Hint: Correct assertion: Gabriel phthalimide reaction can be used to prepare alkyl and aryl alkyl primary amines.
Correct reason: Alkyl and aralkyl halides undergo nucleophilic substitution reaction but aryl halides do not.

25. Assertion: Aniline does not undergo Friedel Craft’s reaction.
Reason: Friedel crafts reaction is an electrophilic substitution reaction.
(a) Both assertion and reason are true and reason is the correct explanation of assertion.
(b) Both assertion and reason are true and reason is not the correct explanation of assertion.
(c) Assertion is true but reason is false.
(d) Both assertion and reason are false.
Answer:
(b)
Hint: Correct explanation: AlCl₃ forms a salt with aniline (C₆H₅NH₂⁺ AlCl₃^–) which deactivates the benzene ring thereby preventing Friedel craft’s reaction.

Students get through the TN Board 12th Chemistry Important Questions Chapter 12 Carbonyl Compounds and Carboxylic Acids which is useful for their exam preparation.

TN State Board 12th Chemistry Important Questions Chapter 12 Carbonyl Compounds and Carboxylic Acids

Answer the following questions.

Question 1.
Write the IUPAC names of the following:

Answer:
(i) 3-phenyl prop-2-en-l-al
(ii) cyclohexanecarbaldehyde
(iii) 3-oxopentan-l-al
(iv) But-2-en-l-al

Question 2.
Give the structure of the following compounds.
(i) 4 – Nitropropiophenone
(ii) 2 – Hydroxycyclopentane carbaldehyde
(iii) phenyl acetaldehyde
Answer:

Question 3.
Write the IUPAC names of
(i) Diacetone alcohol
(ii) Crotonaldehyde
Answer:
(i) 4-Hydroxy-4-methylpentan-2-ol
(ii) But-2-en-l-al

Question 4.
Write the structure of
(i) 3 – oxopentanal
(ii) 1 – phenylpentan – 1 – one
Answer:

Question 5.
Name the following compounds according to IUPAC system of nomenclature.
(i) CH₃CH(CH₃)CH₂CH₂CHO
(ii) CH₃CH₂CO(C₂H₅)CH₂CH₂Cl
(iii) CH₃CH=CHCHO
(iv) CH₃COCH₂COCH₃
(v) CH₃CH(CH₃)CH₂(CH₃)₂COCH₃
(vi) (CH₃)₃CCH₂COOH
(vii) OHCC₆H₄CHO(P)
Answer:
(i) 4-methyl pentanal
(ii) 6-chloro-4-ethylhexan-3 -one
(iii) But-2-en-l-al
(iv) Pentane 2,4, dione
(v) 3, 3, 5 Trimethylhexan – 2 – one
(vi) 3, 3, Dimethyl butanoic acid
(vii) Benzene 1,4, dicarbaldehyde

Question 6.
Draw the structures of the following compounds.
(i) 3-methyl butanal
(ii) 4-nitro propiophenone
(iii) p-methyl benzaldehyde
(iv) 4-methylpent-3-en-2-one
(v) 4-chloropentan-2-one
(vi) 3-Bromo-4-phenyl pentanoic acid
(vii) p, p’ dihydroxy benzo phenone
(viii) Hex-2-en-4 yonic acid
Answer:

Question 7.
Write IUPAC names of the following aldehydes and ketones. Wherever possible give also common names.
(i) CH₃CO(CH₂)₄CH₃
(ii) CH₃CH₂CH(Br)CH₂CH(CH₃)CHO
(iii) CH₃(CH₂)₄CHO
(iv) Ph—CH=CH.CHO
(v)

(vi) PhCOPh
Answer:

Question 8.
Give the product of ozonolysis of the following alkenes.

Answer:
To identify the product of ozonolysis, draw a line in between C=C bond and ‘O’ on either side of the double bond

Question 9.
Identify the products of hydration of the following:
(i) ethyne
(ii) prop-1-yne
(iii) Hex-1-yne
(iv) Diphenyl acetylene
Answer:
Hydration means addition of water. The reagent used is mercuric sulphate and dilute sulphuric acid at 333K. Ketones are formed on hydration of alkynes. MarkovnikofFs mle is followed in water addition.

Question 10.
How are the following compounds formed by distillation of calcium salts of their carboxylic acids?
(i) Formaldehyde,
(ii) Acetaldehyde,
(iii) Acetone,
(iv) Butan-2-one,
(v) Cyclopentanone,
(vi) Benzaldehyde
Answer:
(i) Calcium formate alone is heated.

(ii) By dry distillation of calcium acetate and calcium formate.

(iii) Dry distillation of calcium acetate alone.

(iv) Calcium acetate and calcium propionate are distilled together.

(v) Cyclic ketones are formed when calcium salts of dibasic acids are heated.

(vi) By dry distillation of a mixture of calcium benzoate and calcium formate.

Question 11.
Complete the following equations:

Answer:

Question 12.

(i) Identify the product.
(ii) Name the reaction.
(iii) What is the intermediate formed in the reaction.
Answer:
(i) CH₃CHO (acetaldehyde)
(ii) Stephen’s reaction
(iii) CH₃—CH=NH (an imine)
Complete reaction:

Question 13.

(i) Name the reagent i.e., X used for the above reduction.
(ii) Why other reducing agents like H₂, in the presence of a catalyst are not used.
(iii) Write the IUPAC name of the product formed.
Answer:
(i) Diisobutyl aluminium hydride (DIBAL – H) is used as a reducing agent.
X = H₂O
(ii) It selectively reduces alkyl cyanides to imines, which on hydrolysis gives aldehydes. The double bond in the nitrile is not reduced. The other reducing agents reduce the double bond also.
(iii) hex-4-enal is the IUPAC name of the product.

Question 14.
How is benzaldehyde prepared from (i) methyl benzene, (ii) benzene, (iii) benzyl alcohol. Give equations.
Answer:
(i) Oxidation of methyl benzene, using chromyl chloride as oxidising agent gives benzaldehyde. Acetic anhydride and CrO₃ can also be used for reaction.

(ii) Benzene is treated with CO and HCl Benzaldehyde is formed.

This reaction is known as Gattermann- koch reaction.
(iii) Oxidation of benzyl alcohol using PCC (pyridinium chromo chromate) gives benzaldehyde.

Question 15.
Identify the product of the following reactions. Write the complete equation.

Answer:

Question 16.
Give examples for Friedel-crafts acetylation reaction.
Answer:
Refer Question 15 (ii) and (iii). These reaction are called Friedel-crafts reaction. When acetyl chloride is used it is known as acetylation reaction. When benzoyl chloride is used, it is called benzoylation reaction.

Question 17.
The boiling points of aldehydes and ketones are high compared to hydrocarbons and ethers of comparable molecular mass. Explain why?
Answer:
It is due to the weak molecular association in aldehydes and ketones arising out of the dipole-dipole interactions.

Question 18.
Explain nucleophilic addition reaction with an example.
Answer:
The carbonyl carbon carries a small degree of positive charge. Nucleophile such as CN^– can attack the carbonyl carbon and uses its lone pair to form a new carbon – nucleophile ‘σ‘ bond, at the same time two electrons from the carbon – oxygen double bond move to the most electronegative oxygen atom. This results in the formation of an alkoxide ion. In this process, the hybridisation of carbon changes from sp² to sp³.

The tetrahedral intermediate can be protonated by water or an acid to form an alcohol.

eg: Addition of HCN
Attack of CN^– on carbonyl carbon followed by protonation gives cyanohydrins.

Question 19.
Explain why the carbonyl group in aldehydes and ketones is polar.
Answer:
The carbonyl group of aldehydes and ketones contains a double bond between carbon and oxygen. Oxygen is more electronegative than carbon and it attracts the shared pair of electron which makes the carbonyl group as polar and hence aldehydes and ketones have high dipole moments.

Question 20.
What is meant by the following terms? Give an example in each case.
(i) Cyanohydrin,
(ii) Acetal,
(iii) Semicarbazone,
(iv) Aldol
(v) Hemiacetal,
(vi) Oxime
(vii) Ketal,
(viii) Imine,
(ix) 2,4, DNP derivative
(x) Schiff’s base
Answer:
(i) gem – Hydroxy nitriles i.e., compounds containing hydroxyl and cyano groups on the same carbon atom are called cyano hydrins. These are produced by the addition of HCN to aldehydes and ketones in weakly basic medium.

(ii) gem – dialkoxy alkanes in which two alkoxy groups attached to the terminal carbon atom are called acetals. They are produced by the action of an aldehyde with two equivalent of monohydric alcohol in the presence of dry HCl gas.

(iii) Semi carbazones are derivatives of aldehydes and ketones and are produced by the action of semicarbazides on them in a weakly acidic medium.

(iv) Aldols are β – hydroxy aldehydes or ketones and are produced by the condensation of two molecules of the same or one molecule each of two different aldehydes or ketones (containing an alpha hydrogen atom) in the presence of dilute, aqueous NaOH.

(v) α – alkoxy alcohols are called hemi acetals. They are produced by the addition of one molecule of a mono hydric alcohol to an aldehyde in the presence of dry HCl gas.

(vi) Oximes are produced when aldehydes or ketones react with hydroxyl amine in weakly acidic medium.

(vii) gem-dialkoxy alkanes in which two alkoxy groups present on the same carbon atom are called ketals.
They are produced when a ketone is heated with ethylene glycol in the presence of dry HCl gas.


(viii) Compounds containing >C=N group are called imines. These are produced when aldehydes and ketones react with ammonia and its derivatives.

When ‘Z’ = H, alkyl, aryl,—NH, —OH, C₆H₅ etc..,
(ix) 2, 4, dinitro phenyl hydrazones (i.e., 2, 4, DNP derivative) are produced when aldehydes or ketones react with 2,4 dinitro phenyl hydrazine in weakly acidic medium.

(x) Aldehydes and ketones react with primary aliphatic or aromatic amines in the presence of acid form azomethenes or schifTs bases. Schiffs bases may also be regarded as imines.

Question 21.
How does acetaldehyde react with (i) hydroxyl amine, (ii) hydrazine, (iii) phenyl hydrazine, (iv) semicarbazide? Give equations.
Answer:

Question 22.
Give equations for the reaction between
(i) acetaldehyde and sodium bisulphite
(ii) acetone and sodium bisulphite
Answer:

Question 23.
Write the structure of the prodcuts formed when acetone reacts with (i) hydrazine, (ii) phenyl hydrazine, (iii) semicarbazide.
Answer:

Question 24.
What is urotropine? How it is formed? Write its structure.
Answer:
Hexamethelenetetramine is called urotropine. It is formed when formaldehyde reacts with ammonia.
6HCHO + 4NH₃ → (CH₂)₆N₄ + 6H₂O
Structure:

Question 25.
Mention the uses of urotropine.
Answer:

1. Urotropine is used as a medicine to treat urinary infection.
2. Nitration of Urotropine under controlled condition gives an explosive RDX (Research and development explosive). It is also called cyclonite or cyclotri methylenetrinitramine.

Question 26.
What is popoffs rule? How it is used to predict the oxidation products of unsymmetrical ketones.
Answer:
It states that during the oxidation of an unsymmetrical ketone, a (C—CO) bond is cleaved in such a way that the keto group stays with the smaller alkyl group.
Eg:

Question 27.
How will you prepare
(i) diacetone amine from acetone.
(ii) aldimine from acetaldehyde.
(iii) hydrobenzamide from benzaldehyde.
Answer:
(i)

Two molecules of acetone, combine with ammonia to form diacetoneamine.
(ii)

(iii) With ammonia, benzaldehyde forms a complex condensation product called hydrobenzamide.

Question 28.
What is a haloform reaction? Explain with suitable example.
Answer:
Aldehydes and ketones containing CH₃CO group (methyl carbonyl group), on treatment with excess halogen in the presence of an alkali produce a haloform (chloro form, bromo form, iodoform). This reaction is known as haloform reaction.

Question 29.
What is iodoform test? Explain.
Answer:
Compounds containing CH₃CO (methyl carbonyl) group or compounds on oxidation give compounds containing CH₃CO group, when treated with iodine and NaOH gives a yellow precipitate is called iodoform. This is known as iodoform test.

Question 30.
How will you distinguish between by means of a chemical test.
(i) Propanal and propanone
(ii) acetaldehyde and benzaldehyde
(iii) Ethanal and propanal
Answer:
All these pairs of compounds can be distinguished by iodoform test.
(i) Propanone (CH₃ CO CH₃) will answer iodoform test. Propanal will not undergo iodo form test.

(ii) Acetaldehyde (CH₃CHO) will answer iodoform test, whereas benzaldehyde does not answer iodoform test

(iii) Ethanal (acetaldehyde) will answer iodoform test, but not propanal acetaldehyde

Question 31.
Write a short note an aldol condensation.
Answer:
The carbon attached to carbonyl carbon is called α – carbon and the hydrogen atom attached to α – carbon is called α – hydrogen. In presence of dilute base NaOH, or KOH, two molecules of an aldehyde or ketone having α – hydrogen add together to give β – hydroxyl aldehyde (aldol) or β – hydroxyl ketone (ketol). The reaction is called aldol condensation reaction. The aldol or ketol readily loses water to give α, β – unsaturated compounds which are aldol condensation products.
Acetaldehyde when warmed with dil.NaOH gives β – hydroxyl butraldehyde (acetaldol)

Question 32.
Give the mechanism of aldol condensation.
Answer:
Mechanism: The mechanism of aldol condensation of acetaldehyde takes place in three steps.
Step 1: The carbanion is formed as the α – hydrogen atom is removed as a proton by the base.

Step 2: The carbanion attacks the carbonyl carbon of another unionized aldehyde to form an alkoxide ion.

Step 3: The alkoxide ion formed is protonated by water to form aldol.

The aldol rapidly undergoes dehydration on heating with acid to form α – β unsaturated aldehyde.

Question 33.
Give the oxidation products obtained when pentan-2-one is oxidised by (conc.HNO₃).
Answer:
During these oxidations, rupture of the carbon-carbon bonds occur on either side of the keto group giving a mixture of carboxylic acid, each containing less a number of carbon atom. Than the original ketone.

Question 34.
What is crossed aldol condensation? Give an example.
Answer:
Aldol condensation can also takes place between two different aldehydes or ketones or between one aldehyde and one ketone such an aldol condensation is called crossed or mixed aldol condensation. This reaction is not very useful as the product is usually a mixture of all possible condensation products and cannot be separated easily.

Question 35.
What happens when benzaldehyde reacts with (i) acetaldehyde in the presence of dilute NaOH (ii) acetone in the presence of dilute NaOH.
[OR] Explain with examples Claisen – Schmidt condensation.
Answer:
Benzaldehyde condenses with aliphatic aldehyde or methyl ketone in the presence of dil. alkali at room temperature to form unsaturated aldehyde or ketone. This type of reaction is called Claisen – Schmidt condensation.

Question 36.
Write a short note on Cannizaro reaction.
Answer:
In the presence of concentrated aqueous or alcoholic alkali, aldehydes which do not have α – hydrogen atom under go self oxidation and reduction (disproportionation) to give a mixture of alcohol and a salt of carboxylic acid. This reaction is called Cannizaro reaction.
Benzaldehyde on treatment with concentrated NaOH (50%) gives benzyl alcohol and sodium benzoate.

This reaction is an example of disproportion reaction.

Question 37.
Write the mechanism of Cannizaro reaction.
Answer:
Cannizaro reaction involves three steps.
Step 1: Attack of OH^– on the carbonyl carbons.

Step 2: Hydride ion transfer

Step 3: Acid – base reaction

Cannizaro reaction is a characteristic of aldehyde having no α – hydrogen.

Question 38.
Give an example for crossed Cannizaro reaction.
Answer:
When Cannizaro reaction takes place between two different aldehyde (neither containing an α hydrogen atom), the reaction is called as cross cannizaro reaction.

In crossed cannizaro reaction more reactive aldehyde is oxidized and less reactive aldehyde is reduced.

Question 39.
Give an example for benzoin condensation.
Answer:
Benzaldehyde reacts with alcoholic KCN to form benzoin

Question 40.
Complete the following equation.


Answer:

Question 41.
How will you convert ethanal into following compounds?
(i) Butane 1, 3 diol
(ii) But -2-enal
(iii) But-2-enoic acid.
Answer:

Question 42.
Give simple chemical tests to distinguish between the following pairs of compounds.
(i) Acetophenone and benzophenone
(ii) Phenol and benzoic acid
(iii) Pentan -2- one and pentan – 3-one
(iv) Benzaldehyde and acetophenone
Answer:
(i) Acetophenone and benzophenone: Acetophenone being a methyl ketone, when treated with I₂ / NaOH (NaOI) gives a yellow precipitate of iodoform but benzophenone does not give a yellow precipitate.

(ii) Phenol and benzoic acid: NaHCO₃ test: Benzoic acid being a stronger acid than carbonic acid (H₂CO₃) decomposes NaHCO₃ to evolve CO₂, but phenol being weaker than carbonic acid does not.

FeCl₃ Test: Phenol gives a violet colouration with neutral ferric chloride solution, while benzoic acid gives a buff coloured precipitate of ferric benzoate.

(iii) Pentan-2-one and pentan-3-one:
Sodium bisulphite test: 2-Pentanone being a methyl ketone when treated with a saturated solution of sodium bisulphite gives a white precipitate of 2 – pentanone sodium bisulphite addition compound where as 3 – pentanone does not.


(Note: Sterically hindered ketones, do not undergo this reaction, eg: acetophenone)
Iodoform Test: 2 – pentanone, being a methyl ketone, when treated NaOI (I₂ / NaOH) gives a yellow precipitate of iodoform but 3-pentanone does not.

(iv) Benzaldehyde and acetophenone:
AgNO₃ test: Benzaldehye reduces Tollen’s reagent to give a silver mirror (Ag) but acetophenone does not reduce Tollen’s reagent.

Iodoform test: Acetophenone gives a yellow precipitate when treated with I₂ / NaOH but benzaldehyde does not.

Question 43.
What happens when benzaldehyde is treated with
(i) Br₂ in the presence of FeBr₃
(ii) a mixture of conc.H₂SO₄ and conc.HNO₃
(iii) conc.H₂SO₄
(iv) chlorine
(v) chlorine in the presence of FeCl₃
(vi) methyl bromide in the presence of anhydrous AlCl₃.
Answer:
(i) m-bromobenzaldehyde is formed.

(ii) m-nitrobenzaldehyde is formed.

(iii) m- benzaldehyde sulphonic acid is formed:

(iv) Benzoyl chloride is formed:

(v) m-chloro benzaldehyde is formed:

Question 44.
Mention the uses of (i) formaldehyde (ii) urotropine (iii) acetaldehyde (iv) acetone (v) benzaldehyde (vi) acetophenone and benzophenone.
Answer:
Formaldehyde:

1. 40% aqueous solution of formaldehyde is called formalin. It is used for preserving biological specimens.
2. Formalin has hardening effect, hence it is used for tanning.
3. Formalin is used in the production of thermosetting plastic known as bakelite, which is obtained by heating phenol with formalin.

Urotropine:

1. Urotropine is used as a medicine to treat urinary infection.
2. Nitration of Urotropine under controlled condition gives an explosive RDX (Research and development explosive). It is also called cyclonite or cyclotri methylene trinitramine.

Acetaldehye:

1. Acetaldehyde is used for silvering of mirrors.
2. Paraldehyde is used in medicine as a hypnotic.
3. Acetaldehyde is used in the commercial preparation of number of organic compounds like acetic acid, ethyl acetate etc.,

Acetone:

1. Acetone is used as a solvent, in the manufacture of smokeless powder (cordite).
2. It is used as a nail polish remover.
3. It is used in the preparation of sulphonal, a hypnotic.
4. It is used in the manufacture of thermosoftening plastic Perspex.

Benzaldehyde is used:

1. as a flavoring agent
2. in perfumes
3. in dye intermediates
4. as starting material for the synthesis of several other organic compounds like cinnamaldehyde, cinnamic acid, benzyl chloride etc.

Aromatic Ketones:

1. Acetophenone has been used in perfumery and as a hypnotic under the name hyphone.
2. Benzophenone is used in perfumery and in the preparation of benzhydrol drop.

Question 45.
Give equation for the following reactions.
(i) Nitration of acetophenone
(ii) Bromination of benzophenone
(iii) Friedel – crafts alkylation of benzo phenone
Answer:

Question 46.
Explain the structure of carboxylic acid group.
Answer:
A carboxyl group is made up of a carboxyl group joined to a hydroxyl group.

In the carboxyl group, the carbon atom is attached to two carbon atoms: one by a double bond and the other by a single bond which in turn linked to a hydrogen atom by a single bond. The remaining free valency of the carbon atom of the carboxyl is satisfied by a H atom or an alkyl group. Thus, the structure of carboxylic acids.

where ‘R’ is ‘H’ or alkyl group.
The carbon atom and the two oxygen atoms are sp2 hybridised. The two sp² hybridesed orbitals of the carboxyl carbon overlap with one sp² hybridised orbital of each oxygen atom while the third sp² hybridised orbital of carbon overlaps with either a ‘s’ orbital of H – atom or a sp³ hybridised orbital of ‘C’ atom of the alkyl group to form three a bonds. Each of the two oxygen atoms are left with one unhybridised orbital which is perpendicular to the a bonding skeleton.

All the three ‘p’ orbitals being parallel, overlap to form n bond which is partly delocalised between carbon and oxygen atoms on one side and carbon and oxygen of the ‘OH’group on the other side.

In other words, RCOOH may be represented as a resonance hybrid of the following two canonical structures.

As a result of resonance (i) the C—O single bond length in carboxylic acids is shorter than the normal C—O single bond in alcohols and ethers and (ii) C=O bond length in carboxylic acids is slightly larger than the normal C=O bond length in aldehydes and ketones.

Question 47.
How is acetic acid prepared from (i) ethanol (ii) methyl cyanide (iii) ethyl acetate (iv) methyl magnesium bromide (v) acetyl chloride (vi) acetic anhydride? Give equation.
Answer:
(i) Oxidation of ethanol by acidified K₂Cr₂O₇.

(ii) Acid hydrolysis of methyl cyanide.

(iii) Acid hydrolysis of ethylacetate

(iv) Methyl magnesium bromide reacts with carbondioxide and the product formed on hydrolysis gives acetic acid.

(v) Hydrolysis of acetyl chloride

(vi) Hydrolysis of acetic anhydride

Question 48.
Identify X and Y


Answer:
(i) X = C₆H₅COOMg Br; Y = C₆H₅COOH
(ii) X = C₆H₅COOH; Y = C₆H₅COCl
(iii) X = C₆H₅COOH; Y = C₆H₅COONa

Question 49.
Explain why?
(i) Carboxylic acids have higher boiling point than aldehydes, ketones, or even alcohols of comparable molecular mass.
(ii) Lower aliphatic / carboxylic acid are miscible with water while higher carboxylic acids are immiscible with water.
Answer:
(i) Carboxylic acids have higher boiling point ’ than aldehydes, ketones and even alcohols of comparable molecular masses. This is due to more association of carboxylic acid molecules through intermolecular hydrogen bonding.

(ii) Lower aliphatic carboxylic acids (up to four carbon) are miscible with water due to the formation of hydrogen bonds with water. Higher carboxylic acid are insoluble in water due to increased hydrophobic interaction of hydrocarbon part. The simplest aromatic carboxylic acid, benzoic acid is insoluble in water.

Question 50.
How will you convert
(i) Ethyl benzene to benzoic acid
(ii) Isopropyl benzene to benzoic acid
(iii) p-nitro toluene to p-nitrpbenzoic acid
(iv) o-xylene to phthalic acid
(v) But-2-ene to ethanoic acid
(vi) Benzonitrile to benzoic acid
(vii) Ethyl magnesium iodide to propanoic acid
(viii) Ethyl benzoate to benzoic acid
(ix) Benzamide to benzoic acid
(x) Propan – 2 – one to butanoic acid.
Answer:

Question 51.
Which of the following compounds will undergo aldol condensation? Which the Cannizaro reaction, and which neither? Write the structure of the expected products of aldol condensation and Cannizaro reaction.
(i) Methanal
(ii) 2 – methylpentanal
(iii) Benzaldehyde
(iv) Benzophenone
(v) Cyclohexanone
(vii) Phenyl acetaldehyde
(viii) Butan-1-ol
(ix) 2, 2-dimethyl butanal
Answer:
I. 2 – methyl pentanal
Cyclohexanone
1 – phenyl propanone and phenyl acetaldehyde
contain one or more a hydrogen and hence undergo aldol condensation.



II. Methanal, benzaldehyde, and 2,2 dimethyl butanal do not contain a hydrogen atoms and hence undergo cannizaro reaction. The reaction and structures are:

III. Benzophenone is a ketone with no a hydrogens while butan-1-ol is an alcohol. Both of these neither undergo aldol condensation nor cannizaro reaction.

Question 52.
Give equations for reactions of acetic acid with the following reagents.
(i) Na (ii) NaOH (iii) Na₂CO₃ (iv) PCl₅ (v) SOCl₂ (vi) C₂H₅OH (vii) LiAlH₄ (viii) Red P and HI (ix) Sodalime (x) NH₃ followed by heating (xi) Cl₂ / Red P.
Answer:

Question 53.
Show how each of the following could be converted to benzoic acid:
(i) Ethyl benzene,
(ii) acetophenone,
(iii) benzophenone,
(iv) phenyl ethene.
Answer:

Question 54.
What is esterification? Give an example.
Answer:
The formation of an ester by the action of carboxylic acid and alcohol in the presence of an acid is called esterification.

In these reaction the C—OH bond in acids is cleaved.

Question 55.
Give a brief accounts of decarboxylation reaction.
Answer:
Removal of CO₂ from carboxyl group in called as decarboxylation. Carboxylic acids lose carbon di oxide to form hydrocarbon when their sodium salts are heated with soda lime (NaOH and CaO in the ratio 3:1)

Question 56.
Suggest a suitable reagent to bring about the following conversions. Give equations.
(i) Acetic acid to acetyl chloride
(ii) Benzoic acid to ethyl benzoate
(iii) m – nitro benzoic acid to m – nitro methyl benzoate
(iv) Ethanoic acid to ethanol
(v) Acetic acid to ethane
Answer:
(i) PCl₅ or SOCl₂

(ii) C₂H₅OH in the presence of dil H₂SO₄

(iii) Methyl alcohol in the presence of dil. H₂SO₄

(iv) Lithium aluminium hydride

(v) HI in the presence of Red phosphorus

Question 57.
Give the products of the following:


Answer:
All these reactions are decarboxylation reactions. In these reactions the COONa group is replaced by ‘H’.

Question 58.
What is HVZ reaction? Give an example.
Answer:
Carboxylic acids having an α – hydrogen are halogenated at the α – position on treatment with chlorine or bromine in the presence of small amount of red phosphorus to form α halo carboxylic acids. This reaction is known as Hell-Volhard-Zelinsky reaction (HVZ reaction) The α-Halogenated acids are convenient starting materials for preparing α – substituted acids, eg:
Substitution reaction in the hydrocarbon part α – Halogenetion:

Question 59.
Explain why the ‘COOH’ group in benzoic acid in meta directing.
Answer:
The structure of benzoic acid is a resonance hybrid of the following canonical structure.

Because of -M effect of carboxylic acid, the ortho and para positions becomes less in electron density relative to the meta position, i.e., meta-position becomes rich in electron density compared to ortho and para positions. Hence, the electrophile attacks the meta position, i.e., the COOH group deactivates the benzene ring and is the meta directing group.

Question 60.
How are the following compounds prepared from benzoic acid?
(i) m- Bromo benzoic acid
(ii) m- nitro benzoic acid
(iii) m-sulpho benzoic acid.
Answer:
(i) Bromination of benzene gives m – bromo benzoic acid.

(ii) Nitration of benzene using nitrating mixture gives m – nitro benzoic acid.

(iii) Sulphonation of benzene, using fuming sulphuric acid gives m – sulpho benzoic acid.

Question 61.
Formic acid is a reducing agent. Substantiate this statement with examples.
Answer:
Formic acid contains both an aldehyde as well as an acid group. Hence, like other aldehydes, formic acid can easily be oxidised and therefore acts as a strong reducing agent.

(i) Formic acid reduces Tollens reagent (ammonical silver nitrate solution) to metallic silver.

(ii) Formic acid reduces Fehlings solution. It reduces blue coloured cupric ions to red coloured cuprous ions.

Question 62.
Give the tests for carboxylic acid group in an organic compound.
Answer:

1. In an aqueous solution, carboxylic acid turns blue litmus red.
2. Carboxylic acids give brisk effervescence with sodium bicarbonate due to the evolution of carbon dioxide.
3. When a carboxylic acid is warmed with alcohol and conc.H₂SO₄ it forms an ester, which is detected by its fruity odour.

Question 63.
Give a brief account of the acidity of carboxylic acids.
Answer:
Carboxylic acids undergo ionization to produce H⁺ and carboxylate ions in an aqueous solution. The carboxylate anion is stabilized by resonance which makes the carboxylic acid to donate the proton easily.

The resonance structure of carboxylate ion are given below.

The strength of carboxylic acid can be expressed in terms of the dissociation constant(K_a):

The dissociation constant is generally called acidity constant because it measures the relative strength of an acid. The stronger the acid, the large will be its K_a value.
The dissociation constant of an acid can also be expressed in terms of p^K_a value.
pK_^a = log K_a
A stronger acid will have higher K_a value but smaller pK_^a value, the reverse is true for weaker acids.

Question 64.
Briefly discuss the effect of substituents on the acidity of carboxylic acids.
Answer:
Effect of substituents on the acidity of carboxylic acid.
(i) Electron releasing alkyl group decreases the acidity: The electron-releasing groups (+1 groups) increase the negative charge on the carboxylate ion and destabilize it and hence the loss of proton becomes difficult. For example, formic acid is more stronger than acetic acid,
eg:

(ii) Electron withdrawing substituents increases the acidity: The electron-withdrawing substituents decrease the negative charge on the carboxylate ion and stabilize it. In such cases, the loss of proton becomes relatively easy.
Acidity increases with increasing electronegativity of the substituents. For example, the acidity of various halo acetic acids follows the order F—CH₂—COOH > Cl—CH₂—COOH > Br—CH₂—COOH > I —CH₃—COOH
Acidity increases with increasing number of electron – withdrawing substituents on the a – carbon.
For example
Cl₃C—COOH > Cl₂CH—COOH > ClCH₂COOH > CH₃COOH
The effect of various, electron withdrawing groups on the acidity of a carboxylic acid follows the order,
—NO₂ > —CN >—F >—Cl >—Br >—I >Ph
The relative acidities of various organic compounds are
RCOOH > ArOH > H₂O > ROH >RC ≡ CH

Question 65.
Fluorine is more electronegative than chlorine even their p- fluoro benzoic acid in weaker than p- chloro benzoic aicd. Explain.
Answer:
Since halogens are far more electronegative than carbon and also possess lone pairs of electrons, they exert both -1 and + M effects. Now, the fluorine, the lone pairs of electrons are present in ‘2p’ orbitals and in chlorine, they are present in ‘3p’ orbitals. Since ‘2p’ orbitals of fluorine and chlorine are of almost equal size, the + M effect is more pronounced in p fluoro benzoic acid than in p-chloro benzoic effect.

Question 66.
Explain why p – nitrobenzoic acid has a higher K_a value than benzoic acid.
Answer:
Higher the K_a value, the stronger is the acid. Thus, p-nitro benzoic acid is a stronger acid than benzoic acid. This is due to

1. Because of — I and -M effect of NO₂ group the electron density in O—H bond decreases. As a result, the —O—H bond becomes weak and hence, p – nitrobenzoic acid easily loses a proton than benzoic acid.
   
2. Due to -1 and -M effect of nitrogroup dispersal of negative charge occurs and hencep -nitro benzoate ion becomes more stable than benzoate ion.
   

Question 67.
Give the IUPAC names of the following compounds,
(i) PhCH₂CH₂COOH
(ii) (CH₃)₂C=CHCOOH CH

Answer:
(i) 3 -phenyl propanoic acid
(ii) 3 -methyl but – 2-enoic acid
(iii) 2 -methylcyclopentane carboxylic acid
(iv) 2, 4, 6 -trinitro benzoic acid or 2, 4, 6-trinitro benzene carboxylic acid.

Question 68.
Explain the mechanism for the reaction.

Answer:
Esterification of carboxylic acids with alcohols is a nucleophilic acyl substitution.
In such reactions the nucleophile first adds to a carbonyl group to give a tetrahedral intermediate which then readily loses the leaving group to give the substitution products. The mechanism involves the following steps.
Step 1: Protonation of the carbonyl group:
In the presence of mineral acids (H₂SO₄ or HCl), the carbonyl group of the carboxylic acid accepts a proton to form protonated carboxylic acid.

Step 2: Nucleophilic attack of the alcohol molecule. As a result of protonation, the carbonyl carbon becomes electrophilic (i.e. more electropositive) and hence readily undergoes nucleophilic attack by lone pairs of electrons on the oxygen atom of the alcohol molecule to form a tetrahedral intermediate (II).

Step 3: Loss of a molecule of water and a proton. The tetrahedral intermediate (II) undergoes a proton transfer to give another tetrahedral intermediate (III). During this proton transfer, the OH group gets converted to – OH₂ group which being a good leaving group is lost as a neutral water molecule. The protonation ester (IV), thus formed, finally loses a proton to give the ester (V).

Question 69.
Give the uses of (i) formic acid (ii) acetic acid (iii) benzoic acid (iv) acetyl chloride (v) acetic anhydride (vi) ethyl acetate.
Answer:
Formic acid: It is used

1. for the dehydration of hides
2. as a coagulating agent for rubber latex
3. in medicine for the treatment of gout
4. as an antiseptic in the preservation of fruit juice.

Acetic acid: It is used

1. as table vinegar
2. for coagulating rubber latex
3. for manufacture of cellulose acetate and poly vinylacetate.

Benzoic acid: It is used

1. as food preservation either in the pure form or in the form of sodium benzoate
2. in medicine as an urinary antiseptic
3. for manufacture of dyes.

Acetyl chloride: It is used

1. as acetylating agent in organic synthesis
2. in detection and estimation of —OH, — NH₂ groups in organic compounds.

Acetic anhydride: It is used

1. acetylating agent
2. in the preparation of medicine like asprin and phenacetin
3. for the manufacture plastics like cellulose acetate and poly vinyl acetate.

Ethyl acetate is used

1. in the preparation of artificial fruit essences
2. as a solvent for lacquers
3. in the preparation of organic synthetic reagent like ethyl acetoacetate.

Uses
Acetamide is used in the preparation of primary amines.

Question 70.
A compound with molecular formula, C₄H₁₀O₃ on acetylation with acetic anhydride gives a compound with molecular weight 190. Find out the number of hydroxyl groups present in the compound.
Answer:
During acetylation one ‘H’ atom (at mass = 1 amu) of the OH group is replaced by an acetyl group (CH₃CO – molar mass = 43 amu)
—OH + (CH₃CO)₂O → —O—COCH₃ + CH₃COOH
In other words acetylation of each OH group increases the molecular mass by 43 – 1 = 42 amu. Now that the molecular mass of the compound C₄H₁₀O₃ = 106 amu, while that of the acetylated product is 190 amu. Therefore the number of ‘OH’ groups present in the compound is \(\frac{190-106}{42}\) =2.

Question 71.
Explain (i) Perkins’ reaction (ii) Knoevenagal reaction.
Answer:
(i) Perkins’ reaction:
When an aromatic aldehyde is heated with an aliphatic acid anhydride in the presence of the sodium salt of the acid corresponding to the anhydride, condensation takes place and an α, β unsaturated acid is obtained. This reaction is known as Perkin’s reaction.

(ii) Knoevenagal reaction:

Benzaldehyde condenses with malonic acid in presence of pyridine forming cinnamic acid, Pyridine act as the basic catalyst.

Question 72.
Give names of reagents which bring about the following conversions.
(i) Hexan-1-ol to hexanal
(ii) Cyclohexanol to cyclohexanone
(iii) p-fluorotoluene to p-fluorobenzaldehyde,
(iv) Ethanenitrile to ethanal
(v) allyl alcohol to propenal
(vi) But-2-ene to ethanal
Answer:

Question 73.
Bring out Che following conversions.
(i) Benzyl alcohol to phenyl ethanoic acids.
(ii) 3 – nitrobromo benzene to – 3 – nitrobromo benzoic acid
(iii) Methyl acetophenone to benzene 1, 4, dicarboxylic acid
(iv) cyclohexene to hexane 1, 6 dicarboxylic acid.
Answer:

Question 74.
Identify A – E in the following reactions:
Answer:

Question 75.
Write a short note on the electrophilic substitution reaction of benzaldehyde.
Answer:
The ‘CHO’ group in benzaldehyde deactivates the benzene ring due to its —M effect. As a result the electron densities in ortho and para position are decreased compared to the meta position, i.e, The meta position is electron rich compared to ortho and para position. Hence electrophilic substitution reaction occur at meta position.

Question 76.
Which acid of each pair shown here would you expect to be stronger?


Answer:
(i)

(ii) Due to much stronger -1 effect of F over Cl FCH₂ COO^– ion is much more stable than ClCH₂COO ion and hence FCH₂COOH is a stronger acid than ClCFI₂COOH.
(iii)

Inductive effect decreases with increasing distance, therefore, -I effect of is somewhat stronger in 3-fluorobutanoic acid than in 4-fluorobutanoic acid. In other words, CH₃CHCH₂COCT ion is in more stable than
FCH₂CH₂CH₂COO^– ion and hence  is a stronger acid than FCH₂CH₂CH₂COOH.
Therefore due to greater stability of CF₃—C₆H₄—COO^– (p) ion over CH₃—C₆H₄COOH^– (p) is a stronger acid than H₃CC₆H₄—COOH (p).
(iv)

Question 77.
Identify A to E in the following reactions:
Answer:

(Note: NaBH₄ reduces COCl to CH₂OH, but does not reduce NO₂ to NH₂ group.)

Question 78.
How will you bring about the following conversions in not more than two steps?
(i) Propanone to propene
(ii) Benzoic acid to benzaldehyde
(iii) Ethanol to 3 – hydroxy butanal
(iv) Benzene to m – nitrobenzene
(v) Benzaldehyde to benzophenone
(vi) bromo benzene to 1-phenyl ethanol
(vii) Benzaldehyde to 3 phenylpropan-1-ol
(viii) Benzaldehyde to a – hydroxy phenyl acetic acid
(ix) Benzoic acid to p-nitrobenzyl alcohol.
Answer:
(i) Propanone to propene:

(ii) Benzoic acid to benzaldehyde

(iii) Ethanol to 3 – hydroxy butanal:

(iv) Benzene to m – dinitrobenzene:

(v) Benzaldehyde to benzophenone:

(vi) Bromobenzene to 1 – phenyl ethanol:

(vii) Benzaldehyde to 3 – phenylpropan – 1 – ol:

(viii) Benzaldehyde to a – hydroxyphenyl acetic acid:

(ix) Benzoic acid to m-nitrobenzyl alcohol:

Question 79.
What is transesterification? Give an example.
Answer:
Esters of an alcohol can react with another alcohol in the presence of a mineral acid to give the ester of second alcohol. The interchange of alcohol portions of the esters is termed transesterification.

Question 80.
Give an example for Claisen condensation.
Answer:
Esters containing at least one α – hydrogen atom undergo self-condensation in the presence of a strong base such as sodium ethoxide to form β – keto ester. This reaction is known as Claisen condensation.

Question 81.
How are the following compounds prepared?
(i) acetyl chloride and ethyl chloride from ethyl acetate
(ii) acetamide from acetyl chloride
(iii) Acetamide from acetic anhydride.
Answer:

Question 82.
Complete the following equation:
(i) CH₃COCl + CH₃NH₂ →
(ii) CH₃COCl + (CH₃)₂ NH →
(iii) (CH₃CO)₂O + PCl₅ →
Answer:

Question 83.
How are the following compounds prepared from acetamide?
(i) acetic acid (ii) sodium acetate (iii) methyl cyanide (iv) methyl amine (v) ethyl amine
Answer:

Question 84.
Write the structure and IUPAC names of the following acid derivatives.
(i) acetyl chloride (ii) propionyl chloride (iii) Benzoyl chloride (iv) acetic anhydride (v) propionic anhydride (vi) benzoic anhydride (vii) methyl acetate (viii) Ethyl acetate (ix) phenyl acetate (x) acetamide (xi) propionamide (xii) Benzamide.
Answer:

Question 85.
Briefly explain amphoteric nature of acid amide.
Answer:
Amides behave both as weak acid as well as weak base and thus show amphoteric character. This can be proved by the following reactions.
Acetamide (as base) reacts with hydrochloric acid to form salt.

Acetamide (as acid) reacts with sodium to form sodium salt and hydrogen gas is liberated.

Question 86.
An unknown aldehyde (A) on reaction with alkali gives a β – hydroxy aldehyde which loses water to form an unsaturated aldehyde, 2-butanal. Another aldehyde (B) undergoes a disproportionation reaction in the presence of conc.alkali to form products (C) and (D). (C) is an aryl alcohol with formula C₇H₈O. Identify (A) and (B).
(ii) Write the sequence of chemical reaction involved.
(iii) Name the product, when (B) reacts with zinc amalgam and hydrochloric acid.
Answer:
Since the aldehyde (A) oft reaction With alkali gives a β – hydroxy aldehyde (i.e, an aldol), which loses water to form 2 – butanal (an unsaturated aldehyde) ‘A’ must be acetaldehyde.

Since aldehyde (B) on treatment with conc.alkali undergo disproportionation (i.e., Cannizaro reaction) to give two products (C) and (D). One of these products must be an alcohol and the other must be the corresponding acid. Further, since, the product (C) is an aryl alcohol with molecular C₇H₅O, (C) must be benzyl alcohol, (i.e, C₆H₅ aryl group) OH is alcoholic group C₆H₅O. C₇H₈O—C₆H₆O = CH₂. i.e, C₆H₅CH₂OH. (D) must be sodium benzoate and aldehyde (B) must be benzaldehyde.

Thus aldehyde (A) is acetaldehyde, (B) is benzaldehyde.
(ii) The sequence of reaction is already explained above.
(iii) When (B) reacts with Zn—Hg / HCl, toluene obtained.

Question 87.
A compound ‘X’ (C₂H₄O) on oxidation gives ‘Y’ (C₂H₄O₂). X undergoes a haloform reaction. On treatment with HCN, (X) forms (Z) which on hydrolysis gives 2 – hydroxy propanoic acid.
(i) Write down the structures of ‘X’ and ‘Z’.
(ii) Name the product when ‘X’ is treated with dilute NaOH.
(iii) Write down the equation for the reaction involved.
Answer:
(a) Since the MF C₂H₄O of X corresponds to the general formula C_nH_2nO, characteristic of aldehydes or ketones. (X) may either be an aldehyde or ketone. Since ketone must have at least ‘3’ carbon atoms but X (C₂H₄O) has only ‘2’ two. Therefore (X) must be an aldehyde. The only possible aldehyde is CH₃CHO (MF C₂H₄O) (acetaldehyde).
If (X) is acetaldehyde, than the compound (Z) is acetic acid (CH₃COOH).
(b) (X) is acetaldehyde is confirmed by the following reaction.
(i) It undergoes haloform reaction
(i.e.,)

(ii) On treatment with KCN, acetaldehyde forms a cyanohydrin (Z) which on hydrolysis gives 2 – hydroxy propanoic acid.

(iii) In the presence of dilute NaOH, acetaldehyde undergoes aldol condensation to form 3- hydroxy butanal commonly called aldol.

Choose the correct answer:

1. The IUPAC name of the compound is

(a) Mesityl oxide
(b) 4- methyl pent – 3 – en – 2 – one
(c) 4 – methyl pent – 2 – en – 4 – one
(d) 2 – methyl pent – 4 – one
Answer:
(b)

2. Ozonolysis of 2-methyl but-2-ene followed by treatment with Zn/H₂O gives:
(a) ethanal
(b) propanone
(c) propanal and prop – 2 – one
(d) ethanal and propan – 2 – one
Answer:
(d)
Hint:

3. Identify the product ‘Y’ in the following reaction sequence.

(a) pentane
(b) cyclobutane
(c) cyclopentane
(d) cyclopentanone
Answer:
(c)
Hint:

4. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having molecular mass 44 u. The alkene is:
(a) 2 – butene
(b) ethene
(c) propene
(d) 1 – butene
Answer:
(a)
Hint: The aldehyde with molecular mass 44 u is CH₃CHO (acetaldehyde). Therefore the symmetrical alkene is 2 – butene.

5. Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the presence of:
(a) a vinyl group
(b) an isopropyl group
(c) an acetylene triple bond
(d) two ethylenic double bonds
Answer:
(a)
Hint:

6. Identify the compound ‘X’ in the following reaction:

Answer: (a)
Hint:

7. The order of reactivity of phenyl magnesium bromide (PhMgBr) with the following compounds.
I. CH₃CHO,
II. (CH₃)₂CO and
III. PhCOPh is:
(a) III > II > I (b) II > I > III
(c) I > III > II (d) I > II > III
Answer:
(d)
Hint: Reaction between RMgX with carbonyl compound is nucleophilic addition. The greater the positive charge on the carbonyl carbon, the faster is the rate of nucleophilic addition.

8. A carbonyl compound reacts with hydrogen cyanide to form a cyanohydrin which on hydrolysis forms a racemic mixture of a – hydroxy acids. The carbonyl compound is:
(a) formaldehyde
(b) acetaldehyde
(c) acetone
(d) diethyl ketone
Answer:
(b)
Hint: Acetaldehyde cyanohydrin on hydrolysis gives lactic acid
This contains a chiral carbon and exists as a racemic mixture. All other compounds are symmetrical and hence, their cyanohydrins and their corresponding α – hydroxy acids are not optically active because they do not contain chiral carbon.

9. In a set of reactions, acetic acid yielded the product D

The structure of ‘D’ would be:

Answer:
(a)
Hint:

10. (CH₃)₂C=CHCOCH₃ can be oxidised to (CH₃)₂C=CHCOOH by:
(a) Chormic acid
(b) NaOI
(c) Cu at 300°C
(d) KMnO₄
Answer:
(b)
Hint:

11. A compound ‘A’ (C₅H₁₀C₃₁₂) on hydrolysis gives C₅H₁₀O which reacts with NH₂OH, forms iodoform but does not give Fehling’s test A is:

Answer:
(a)
Hint: Since the compound ‘A’ on hydrolysis gives C₅H₁₀O does i ot reduce Fehlings solution but reacts with NH₂OH, forms iodoform, it must be methyl ketone.

12. Acetophenone, when reacted with a base, C₂H₅ONa, yields a stable compound that has the structure:

Answer:
(c)
Hint:

13.

The structure of ‘B’ is:

Answer: (a)
Hint:

14. Self-condensation of two moles of ethyl acetate in presence of sodium ethoxide yields:
(a) ethyl propionate
(b) ethyl butyrate
(c) acetoacetic ester
(d) methyl acetoacetate
Answer:
(c)
Hint:

15. m- chlorobenzaldehyde on reaction with conc. KOH at room temperature gives:
(a) potassium-m-chloro benzoic acid and m-hydroxy benzaldehyde.
(b) m-hydroxy benzaldehyde and m-chloro benzyl alcohol.
(c) m-chloro benzyl alcohol and m-hydroxy benzyl alcohol.
(d) potassium-m-chloro benzoate and m-chloro benzyl alcohol.
Answer: (d)
Hint:

16. Consider the following compounds:

Which will give the iodoform test?
(a) only I
(b) both I and II
(c) only II
(d) all
Answer:
(c)
Hint: Although contains a CH₃CO group linked to carbon, it does not undergo iodoform test. This is because iodination occurs at the more reactive CH₂ group rather than terminal CH₃ which is essential for iodoform test to occur

17. Fehling solution will oxidise:

(a) All
(b) only I and IV
(c) only II and IV
(d) only III and IV
Answer:
(d)
Hint: Fehling solution oxidises only aliphatic aldehydes

18.

The product ‘Z’ is:
(a) benzaldehyde
(b) benzoic acid
(c) benzene
(d) toluene
Answer:
(b)
Hint:
X = Benzene
Y = Toluene
Z = Benzoic acid

19. Match entries of column I with appropriate entries of column II.

(a) (A) – (p)- (B) – (s)- (C) – (q); (D) – (r)
(b) (A) – (q); (B) – (s); (C) – (p); (D) – (r)
(c) (A) – (r); (B) – (s); (C) – (p); (D) – (q)
(d) (A) – (r); (B) – (p); (C) – (q); (D) – (s)
Answer:
(c)

20. Assertion: Fehling solution oxidizes acetaldehyde to acetic acid but not benzaldehyde to benzoic acid.
Reason: The C—H bond in benzaldehyde is stronger than acetaldehyde.
(a) Both assertion and reason are correct and the reason is the correct explanation of assertion.
(b) Both assertion and reason are correct but the reason is not the correct explanation of assertion.
(c) Assertion is true but reason is wrong.
(d) Both assertion and reason are wrong.
Answer:
(a)

21. Assertion: Carboxylic acids contain a carbonyl group but do not give characteristic reactions of the carbonyl group.
Reason: Due to resonance, the electrophilic nature of the carboxyl cation is greatly reduced as compared to carbonyl carbon in aldehydes and ketones.
(a) Both assertion and reason are correct and the reason is the correct explanation of assertion.
(b) Both assertion and reason are correct but the reason is not the correct explanation of assertion.
(c) Assertion is true but the reason is wrong.
(d) Both assertion and reason are wrong.
Answer:
(a)

22. Among the following acids which has the lowest pK_a value?
(a) CH₃COOH
(b) HCOOH
(c) (CH₃)₂CHCOOH
(d) CH₃CH₂COOH
Answer:
(b)
Hint: HCOOH is the strongest acid and hence the lowest pK_a value.

23. Which of the following presents the correct order of the acidity in the given compounds?
(a) FCH₂COOH > ClCH₂COOH > BrCH₂COOH > CH₃COOH
(b) CH₃COOH > BrCH₂COOH > ClCH₂COOH > FCH₂COOH
(c) FCH₂COOH > CH₃COOH > BrCH₂COOH > ClCH₂COOH
(d) BrCH₂COOH > ClCH₂COOH > FCH₂COOH > CH₃COOH
Answer:
(a)

24. The correct acidity order of the following is

(a) III > IV > II > I
(b) IV > III > I > II
(c) III > II > I > IV
(d) II > III > IV > I
Answer: (a)
Hint: Carboxylic acids are stronger than phenols. Further, electrons donating groups decrease the acidity of phenol/carboxylic acid while electron-withdrawing groups increase the acidity of phenol/carboxylic acid. Thus, the over all order.
III > IV > II > I

25. Which one of the following pairs gives effervescence with aq.NaHCO₃
I. CH₃COCI
II. CH₃COCH₃
III. CH₃COOCH₃
IV. CH₃COOCOCH₃
(a) I and II
(b) I and IV
(c) II and III
(d) I and III
Answer:
(b)
Hint: Both CH₃COCl and CH₃COOCOCH₃ react with water to produce acids and hence give effervescence with NaHCO₃.

26. Propionic acid with Br₂/P yields a dibromo product. Its structure would be:
(a) CH(Br)₂—CH₂COOH
(b) CH₂(Br)CH₂COBr
(c) CH₃C(Br)₂COOH
(d) CH₂(Br)CH(Br)COOH
Answer:
(c)
Hint:Bromination occurs at a position.

27. When benzoic acid is treated with LiAlH₄, it forms:
(a) benzaldehyde
(b) benzyl alcohol
(c) benzene
(d) toluene
Answer:
(b)

28. Sodium ethoxide reacts with ethanoyl chloride. The compound that is produced in the above reaction is:
(a) 2-butanone
(b) ethyl chloride
(c) ethyl ethanoate
(d) diethyl ether
Answer:
(c)
Hint: CH₃COCl + C₂H₅ONa → CH₃COOC₂H₅ + NaCl

29. Consider the following:

The correct decreasing order of their reactivity towards hydrolysis is:
(a) II > IV > I > III
(b) II > IV > III > I
(c) I > II > III > IV
(d) IV > II > I > III
Answer:
(a)
Hint: Electron donating groups decrease while electron-withdrawing groups increase the reactivity of acid chlorides towards hydrolysis.

The reactivity depends on the positive charge on the cabonyl carbon.

Students get through the TN Board 12th Chemistry Important Questions Chapter 11 Hydroxy Compounds and Ethers which is useful for their exam preparation.

TN State Board 12th Chemistry Important Questions Chapter 11 Hydroxy Compounds and Ethers

Answer the following questions.

Question 1.
Classify the following as primary, secondary and tertiary alcohols.


Answer:
Primary alcohols: (i), (ii), (iii)
Secondary alcohols: (iv), (v)
Tertiary alcohol: (vi)

Question 2.
Identify allyl alcohols in the above (Q.No. 1) examples.
Answer:
(ii) and (vi).

Question 3.
Name the following compounds according to IUPAC system:
Answer:

Question 4.
Write IUPAC names of the following:
Answer:

Question 5.
Write the structures of the compounds whose IUPAC names are as follows:
Answer:

Question 6.
Complete the following reactions:


Answer:

Question 7.
Using suitable Grignard reagent and a carbonyl compound, how will you prepare
(i) phenyl methanol,
(ii) butan-2-ol,
(iii) 2-methylhexan-2-ol,
(iv) propan-2-ol.
Answer:
(i) phenyl methanol:

(ii) butan-2-ol:

(iii) 2-methylhexan-2-ol:

(iv) propan-2-ol:

Question 8.
Give equation for the preparation of 2-methyl-2-propanol using a suitbale Grignard reagent and a carbonyl compound.
Answer:
Tertiary containing at least two identical groups can be prepared by the addition of a Grignard reagent to an ester other the formic ester followed by acid hydrolysis.

Question 9.
Name the reducing agents that will convert a carbonyl compound to an alcohol. Give an example for each.
Answer:
Raney Ni, / Sodium analgen in H₂O (Na—Hg/H₂O), H₂ in the presence of Pt.

where ‘R’ is an alkyl group.

Question 10.
Why is LiAlH₄ is used to reduce crotonaldehyde?
Answer:
Li crotonaldehyde is an unsaturated aldehyde (CH₃CH=CHCHO). Lithium aluminium hydride selectively reduces ‘CHO’ group to ‘CH₂OH’ group without affecting the C=C.

Question 11.
Name the product formed when sodium borohydride is used as a reducing agent for the reduction of a compound containing both carbonyl and carboxyl group, (or) Identify the product:
Answer:

Question 12.
Complete the following reactions:


Answer:

Question 13.
How is glycerol prepared from triglycerides or fats?
Answer:
The alkaline hydrolysis of these fats gives glycerol and the reaction is known as saponification.

Question 14.
Complete the following equations:

Answer:

Question 15.
Give mechanism of reaction between alcohols and halogen acids.
Answer:
Primary alcohols react by S_N2 mechanism while secondary and tertiary alcohol react by S_N1 mechanism.

Question 16.
How will you distinguish between

Answer:

(ii) Secondary alcohol will give a blue colour as shown above whereas a tertiary alcohol will not produce any colour.

Question 17.
Give the structures of the products you would expect when each of the following alcohol reacts with (a) HCl-ZnCl₂, (b) HBr, (c) SOCl₂ (i) Butan-l-ol and (ii) 2-methylbutan-2-ol.
Answer:
(a) with HCl-ZnCl₂ (Lucas reagent):
[2-methylbutan-2-ol being a tertiary alcohol reacts with Lucas reagent to produce turbidity immediately due to formation of insoluble tert-alkyl-halide, while butan-l-ol being a primary alcohol does not react with Lucas reagent at room temperature.]

(b) with HBr: Both alcohols produce the corresponding alkyl bromides.

(c) with SOCl₂: Both alcohols react to form their corresponding alkyl chlorides.

Question 18.
Arrange the following compounds in increasing order of boiling points, pentan-1 -ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol. Give reason for your answer.
Methanol < ethanol < propan-1-ol < butan-2- ol < butan-1-ol < pentan-1-ol.
Answer:
Boiling point increases regularly as the molecular mass increases due to the corresponding increase in their vander waals forces of attraction. The boiling point increases in the order.
methanol, ethanol, propan-1-ol, butan-1-ol and pentan-1-ol.
Among isomeric alcohol, 2° alcohols have lower boiling point than 1° alcohols due to corresponding decrease in the extent of hydrogen bonding because of steric hindrance. Thus the boiling point of butan-2-ol is lower than butan-1-ol.

Question 19.
Explain why propanol has higher boiling point than that of hydrocarbon butane?
Answer:
The molecuels of butane are held together by weak vander waals forces of attraction while these of propanol are held together by stronger hydrogen bonding.

Therefore boiling point of propanol is higher than that of butane.

Question 20.
Write the mechanism for the reaction

Answer:
The reaction follows S_N1 mechanism.
Step 1: Formation of protonated alcohol.

Step 2: Protonated alcohols forms carbocation.

Step 3: Elimination of a proton to form alkane.

Question 21.
Give mechanism for the formation of prop-1 – ene from propan-1-ol.
Answer:
The reaction is

Mechanism:
Step 1: Formation of protonated alcohol.

Step 2: Formation of carbocation.

Step 3: Elimination of a proton.

Question 22.
State Saytzeff rule.
Answer:
During intramolecular dehydration, if there is a possibility to form a carbon-carbon double bond at different locations, the preferred location is the one that gives the more (highly) substituted alkene i.e., the stable alkene.

Question 23.
Name the reagents in the following reactions:
(i) oxidation of a primary alcohol to a carboxylic acid.
(ii) oxidation of a primary alcohol to an aldehyde.
(iii) benzyl alcohol to benzoic acid.
(iv) butan-2-one to butan-2-ol.
Answer:
(i) Acidified potassium dichromate or neutral or acidic or alkaline potassium permanganate (followed by hydrolysis with dilute H₂SO₄).
(ii) Pyridinium chloro chromate(PCC) in CH₂Cl₂ or pyridinium dichromate (PDC) in CH₂Cl₂.
(iii) Acidified or alkaline KMnO₄ (followed by hydrolysis with dil H₂SO₄).
(iv) Ni/H₂ or NaBH₄ or LiAlH₄.

Question 24.
What happen when,
(i) vapours of ethanol is passed over heated copper at 573 K.
(ii) vapours of propan-2-ol is passed over heated copper at 573 K.
(iii) vapours of 2-methyl propan-2-ol is passed over heated copper at 573 K. Give equation.
Answer:
(i) Ethanal is formed.

(ii) Propanone is formed.

(iii) 2-methyl prop-1-ene is formed.

Question 25.
What is nitroglycerine? How it is formed? Give equation.
Answer:
Glycerotrinitrate (1,2,3, trinitroxy propane) is nitroglycerine. It is formed by nitration of glycerine in the presence of conc. H₂SO₄.

Question 26.
How is acrolein formed from glycerol?
Answer:
When glycerol is heated with dehydrating agents like conc. H₂SO₄, KHSO_4, or P₂O₅ acrolein is formed.

Question 27.
Mention the cause for the acidic nature of alcohols.
Answer:
The acidic character of alcohols is due to the electronegative oxygen atom which withdraws electrons of the O—H bond towards itself. As a result, the O—H bond becomes weak and hence a proton can be easily abstracted by a base, i.e., ionization of alcohol to yield alkoxide ion and H+ ions are facilitated.
ROH ⇌ RO^– + H⁺

Question 28.
Mention the uses of (i) methanol, (ii) ethanol, (iii) ethylene glycol, (iv) glycerol.
Answer:
(i) Uses of methanol:
(a) Methanol is used as a solvent for paints, varnishes, shellac, gums, cement, etc.
(b) In the manufacture of dyes, drugs, perfumes, and formaldehyde.

(ii) Uses of ethanol:
(a) Ethanol is used as an important beverage.
(b) It is also used in the preparation of

• Paints and varnishes.
• Organic compounds like ether, chloroform, iodoform, etc.,
• Dyes, transparent soaps.

(c) As a substitute for petrol under the name power alcohol used as fuel for airplane.
(d) It is used as a preservative for biological specimens.

(iii) Uses of ethylene glycol:
(a) Ethylene glycol is used as an antifreeze in an automobile radiators.
(b) Its dinitrate is used as an explosive with DNG.

(iv) Uses of glycerol:
(a) Glycerol is used as a sweetening agent in confectionery and beverages.
(b) It is used in the manufacture of cosmetics and transparent soaps.
(c) It is used in making printing inks and stamp pad ink and lubricant for watches and clocks.
(d) It is used in the manufacture of explosives like dynamite and cordite by mixing it with china clay.

Question 29.
Alcohols are easily protonated in comparison to phenols. Explain why.
Answer:
In phenols, the lone pair of electrons on the oxygen atom is delocalized over the benzene ring due to resonance and hence, not easily available for protonation. In contrast, in alcohols, the lone pair of electrons on the oxygen atom is localized due to the absence of resonance and hence are easily available for protonation.

Question 30.
Identify the major product obtained in the following reaction:

Answer:

Question 31.
Identify the product of the reaction:

Answer:
In the presence of a weak nucleophile such as ethanol, neopentyl bromide ionizes to form first a 1° carbocation which rearranges to form a more stable 3° carbocation. This is then attacked by the weak nucleophile ethanol followed by a less proton to yield ethyl neopentyl ether.

Question 32.
Show how 2-methyl propan-1-ol is prepared by the reaction of a suitable Grignard reagent.
Answer:

This part that has been enclosed in the box comes from methanal while the remaining part comes from the Grignard reagent. Therefore the Grignard reagent should be isopropyl magnesium bromide. Thus,

Question 33.
Write the structure of the products of the following reactions.

Answer:

(ii) NaBH₄ (sodium bromohydride) is a reducing agent. It reduces aldehydes and ketones but not esters.

(ii) NaBH₄ reduces, -CHO group to CH₂OH group. Thus,

Question 34.
What is esterification? Give an example.
Answer:
Formation of an ester from an alcohol and an organic acid in the presence of a catalyst is known as esterification. In the reaction, the ‘OH’ of the carboxylic acid and ‘H’ of the alcoholic group are removed as water.
Eg:

Question 35.
Why are alcohols are weaker acids than water?
Answer:
In water, ‘O’ atom is attached to two ‘H’ atom, but in alcohols, ‘O’ atom is attached to one ‘H’ atom and one ‘R’ group (alkyl group). Since ‘R’ group has an electron-donating inductive effect (+I), it increases the electron density in the O—H bond compared to that O—H bond in water. In other words, —O—H bond in alcohols is stronger than the —O—H bond in water. As a result, proton removal from alcohol is more difficult than in water. Hence, alcohols are weaker acids than water.

Question 36.
The acidic nature of alcohols is in the order 1° alcohol > 2° alcohol > 3° alcohol. Explain.
Answer:

Alkyl (R) groups are electron releasing (i.e., +I effect) the electron density in the O—H bond in tertiary alcohols is maximum followed by secondary alcohol, while in primary alcohols, it is minimum. This means that O—H bond in tertiary alcohol is the strongest and hence most difficult to break followed by O—H bond in the secondary alcohols, while the O—H bond in primary alcohols is the weakest and hence most easy to break. Thus the acidic strength is in the order.
Primary > Secondary > Tertiary

Question 37.
Arrange the following compounds in increasing order against each.
(i) CH₃CH₂OH, CF₃CH₂OH. CCl₃CH₂OH (acid strength)
(ii) 2-methyl-2-propanol, 1-butanol, 2-butanol (reactivity towards sodium)
Answer:
(i) Due to -I effect of halogens, the electron density in the O—H bond decreases. As a result, the O—H bond strength becomes weak and proton removal is easier compared to CH₃CH₂OH. Further, since fluorine has a stronger -I effect, than chlorine, CF₃CH₂COOH is a stronger acid than CCl₃CH₂COOH. Hence, CF₃CH₂OH is the strongest acid while CH2CH2OH is the weakest acid. Hence increasing order of acid strength is
CH₃CH₂OH < CCl₃CH₂OH < CF₃CH₂OH.
(ii) It is an acid-base reaction since alcohols are acidic and sodium is a strong base. As such, the reactivity of these alcohols towards sodium increases as the acidic character of alcohols increases. Since the acidic character increases in the order 3° < 2° < 1°. Therefore the reactivity towards alcohol increases in the same order.

Question 38.
How will you convert phenol to (i) benzene, (ii) aniline, (iii) phenylacetate, (iv) phenyl benzoate, (v) anisole?
Answer:
(i) Benzene: Phenol is converted to benzene on heating with zinc dust. In this reaction, the hydroxyl group which is attached to the aromatic ring is eliminated.

(ii) Aniline: Phenol on heating with ammonia in presence of anhydrous ZnCl₂ gives aniline.

(iii) Phenyl acetate:

(iv) Phenyl benzoate:

(v) Anisole:

Question 39.
Identify A and B in the following:

Answer:

(ii) A= HNO₂ (273 -278) K
B = H₂O

Question 40.
What is picric acid? How it is prepared? 2,4,6 trinitrophenol is called picric acid.
Answer:
Nitration with cone. HNO₃ and conc.H₂SO₄ gives picric acid.

Question 41.
Give equation for the following:
(i) nitration of phenol,
(ii) sulphonation of phenol,
(iii) nitrosation of phenol.
Answer:
(i) Nitration of phenol: Phenol can be nitrated using 20% nitric acid even at room temperature, a mixture of ortho and para nitro phenols are formed.

(ii) Sulphonation of phenol: Phenol reacts with cone. H₂SO₄ at 280 K to form o-phenol sulphonic acid as the major product. When the reaction is carried out at 373 K the major product is p-phenol sulphonic acid.

(iii) Nitrosation of phenol: phenol can be readily nitrosated at low temperature with HNO₂.

Question 42.
What happens when phenol is treated with
(i) acidified potassium dichromate,
(ii) hydrogen in the presence of nickel as a catalyst,
(iii) bromine water,
(iv) bromine in the presence of CCl₄.
Answer:
Phenol treated with
(i) acidified potassium dichromate (oxidation):
Phenol undergoes oxidation with air or acidified K₂CrO₇ with conc. H₂SO₄ to form 1, 4-benzoquinone.

(ii) hydrogen in the presence of nickel as catalyst (reduction): Phenol on catalytic hydrogenation gives cyclohexanol.

(iii) bromine water (halogenation): phenol reacts with bromine water to give a white precipitate of 2,4,6-tribromo phenol.

(iv) bromine in the presence of CCl₄: If the reaction is carried out in CS₂ or CCl₄ at 278 K, a mixture of ortho and para bromo phenols are formed.

Question 43.
Explain why the phenolic group is ortho para directing.
Answer:
The lone pair of electrons on the oxygen atom of the phenolic group enter into conjugation with the benzene ring due +M effect of the phenolic group. As a result, the ortho and para position become electron-rich compounds to the meta position. Hence the electrophilic attack the ortho and para position.

Question 44.
Write a short note on Reimer-Tiemann reaction.
Answer:
On treating phenol with CHCl₃ / NaOH, a -CHO group is introduced at the ortho position.
This reaction proceeds through the formation of substituted benzal chloride intermediate.

Question 45.
How will you distinguish between alcohol and phenol?
Answer:

1. Phenol reacts with benzene diazonium chloride to form a red-orange dye, but ethanol has no reaction with it.
2. Phenol gives purple coloration with neutral ferric chloride solution, alcohols do not give such coloration with FeCl₃.
3. Phenol reacts with NaOH to give sodium phenoxide. Ethyl alcohol does not react with NaOH.

Question 46.
Mention the uses of phenol.
Answer:

1. About half of the world production of phenol is used for making phenol-formaldehyde resin. (Bakelite).
2. Phenol is a starting material for the preparation of
   (a) drugs such as phenacetin, salol, aspirin, etc.
   (b) phenolphthalein indicator.
   (c) explosive like picric acid.
3. It is used as an antiseptic-carbolic lotion and carbolic soaps.

Question 47.
Give the IUPAC names of the following ethers.


Answer:
(i) 1-ethoxy-2-methyl propane
(ii) 2-chloro-l-methoxy ethane
(iii) 4-nitroanisole
(iv) 1-methoxy propane
(v) 4-ethoxy-1, 1, dimethyl cyclohexane
(vi) ethoxy benzene

Question 48.
Ethers are soluble in water. Give reason.
Answer:
The oxygen of ether can also form hydrogen bonds with water and hence they are miscible with water. Ethers dissolve a wide range of polar and non-polar substances.

Question 49.
Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis.
(i) 1 -propoxypropane
(ii) Ethoxy benzene
(iii) 2-methyl-2-methoxy propane
(iv) 1-methoxyethane
Answer:
(i)

Question 50.
Give the mechanism for the conversion of (i) ethanol to ethoxyethane, (ii) dehydration of 1-propanol to 1-proproxy propane.
Answer:
(i)

[Acid catalyzed 1° alcohol to ethers occurs via S_N2 reaction, involving a nucleophilic attack by the alcohol molecule on the protonated alcohol molecule.]

Question 51.
Explain why the boiling point of ethers is slightly higher than that of alkanes and lower than that of alcohols of comparable molecular mass.
Answer:
Due to weak dipole-dipole interactions, the boiling point of ethers is only slightly higher than those of u-alkanes having comparable molecular masses.
The boiling points of ethers are less than that of alcohols is that ethers do not form hydrogen bonds.

Question 52.
Mention the uses of (i) Diethyl ether and (ii) Anisole.
Answer:
Uses of Diethyl ether:

1. Diethyl ether is used as a surgical anesthetic agent in surgery.
2. It is a good solvent for organic reactions and extraction.
3. It is used as a volatile starting fluid for diesel and gasoline engines.
4. It is used as a refrigerant.

Uses of anisole:

1. Anisole is a precursor to the synthesis of perfumes and insecticide pheromones
2. It is used as a pharmaceutical agent.

Question 53.
Discuss the mechanism of the reaction
CH₃OCH₂CH₃ + HI → CH₃I + CH₃CH₂OH.
Answer:
This reaction is an S_N2 reaction. The cleavage of ethers by halogen acids occurs by the following mechanism.
Step 1: Ethers being Lewis acids, undergo protonation to form oxonium ions.

This reaction takes place with HBr or HI because they are sufficiently acidic.
Step 2: Iodide ion is a good nucleophile. Due to steric hindrance, it attacks the smaller alkyl group of oxonium ion formed in step 1 and displaces the alcohol molecule by S_N2 mechanism as shown below:

Step 3: when excess HI is used, ethanol formed reacts with another molecule of HI to form ethyl iodide.

Question 54.
Explain why ‘OCH₃’ in the anisole group is ortho-para directing.
Answer:
The lone pair of electrons on the oxygen atom of the alkoxy group enters into the conjugation with the benzene ring due to its +M effect.

As a result, the ortho and para position become rich in electron density compared to the meta position. Hence, the electrophile attacks ortho and para position.

Question 55.
Briefly account of dipolar nature of C—O bonds in ethers.
Answer:
Because of the greater electronegativity of oxygen and carbon, the C—O bond is slightly polar thus have a dipole moment. Since the two C—O bonds in ethers are inclined to each other at an angle of 110°, the two dipoles do not cancel each other. As a result, ethers have a dipole moment of 1.15 to 1.3D

Question 56.
Give the equation for the reaction between diethyl ether with an excess of oxygen.
Answer:

Question 57.
Give examples for (i) phthalein fusion and (ii) coupling reaction.
Answer:
(i) Phthalein fusion: On heating phenol with phthalic anhydride in presence of conc. H₂SO₄, phenolphthalein is obtained.

(ii) Coupling reaction: Phenol couples with benzene diazonium chloride in an alkaline solution to form p-hydroxy azobenzene (a red-orange dye).

Choose the correct answer:

1. The IUPAC name of the compound is:

(a) 2-chloro-5- hydroxyhexane
(b) 2-hydroxy-5-chlorohexane
(c) 5-chlorohexan-2-ol
(d) 2-chlorohexan-5-ol
Answer:
(c)

2. The IUPAC name of the compound is:

(a) 1-methoxy-1-methyl ethane
(b) 2-methoxy-2-methyl ethane
(c) 2-methoxypropane
(d) isopropyl-methyl ether
Answer:
(c)

3. Arrange the following compounds in increasing order of boiling point:
I – propan-1-ol
II – butan-1-ol
III – butan-2-ol
IV – pentan-1-ol
(a) I, III, II, IV
(b) I, II, III, IV
(c) IV, III, II, I
(d) IV, II, III, I
Answer:
(a)
Hint: The boiling point increases as the molecular mass increases. Further among isomeric alcohols 1° alcohols have higher boiling points than 2° alcohols.

4. Acid catalysed hydration of alkenes except ethene, leads to the formation of:
(a) primary alcohol.
(b) secondary or tertiary alcohol.
(c) a mixture of primary and secondary alcohol.
(d) a mixture of secondary and tertiary alcohol.
Answer:
(b)
Hint: Hydration of ethene gives a 1° alcohol while all others give a either a 2° alcohol or 3° alcohol.

5. Which of the following Grignard reagent is suitable for the preparation of 3-methyl-2- butanol?
(a) 2-butanone + methyl magnesium bromide
(b) Acetone + ethyl magnesium bromide
(c) Acetaldehyde + isopropyl magnesium bromide
(d) Ethyl propionate + methyl magnesium bromide
Answer:
(c)
Hint:

6. Which of the following esters shown, after reduction with LiAlH₄ and aqueous workup, will yield two molecules of only a single alcohol?
(a) C₆H₅COOC₆H₅
(b) CH₃CH₂COOCH₂CH₃
(c) CH₃COOCH₃
(d) C₆H₅COOCH₂C₆H₅
Answer:
(d)
Hint: Acyl and arylalkyl groups contain the same number of carbon atoms.

7. Which of the following will exhibit highest boiling point?

Answer:
(b)
Hint: Among isomeric alcohols, the alcohol with no branching has the highest boiling point.

8. Consider the reactions:

The mechanisms of reactions (i) and (ii) are respectively:
(a) S_N1 and S_N2
(b) S_N1 and S_N1
(c) S_N2 and S_N2
(d) S_N2 and S_N1
Answer:
(c)

9.

which of the following compounds will be formed?

Answer:
(a)
Hint: Nucleophilic attack occurs on the smaller alkyl group.

10. The reaction of with RMgX leads to the formation of:

Answer:
(d)
Hint:

11.

X is:
(a) bromine in benzene
(b) bromine in water
(c) potassium bromide solution
(d) bromine in CCl₄ at 0° C
Answer:
(b)
Hint:

12. Phenol can be distinguished from ethanol by the following reagent except.
(a) sodium
(b) I₂ / NaOH
(c) neutral FeCl₃
(d) Br₂ / H₂O
Answer:
(a)
Hint: Na reacts with both ethapol and phenol.

13. An ether is more volatile than an alcohol having the same molecular formula. This is due to:
(a) intermolecular hydrogen bonding in alcohols
(b) dipolar character of ethers
(c) alcohols having resonance structures
(d) intermolecular hydrogen bonding in ethers
Answer:
(a)

14. Mark the correct increasing order of reactivity of the following compounds with HBr / HI.

(a) I < II < III
(b) II < I < III
(c) II < III < I
(d) III < II < I
Answer:
(c)
Hint: All the three benzyl alcohols react with HBr or HI through the formation of intermediate carbocation. Obviously more stable the carbocation, more reactive is the alcohol. Now, electron withdrawing group i.e, NO₂, Cl, etc., decrease the stability of carbocations. Since, NO₂ is a stronger, electron withdrawing group, then Cl, stability of carbocation increases in the order.

Therefore, the reactivity of the benzyl alcohols increases in the same orders, i.e., II < III < I.

15. Which of the following reagents can be used to oxidize primary alcohols to aldehydes?
1. CrO₃ in acidic medium,
2. KMnO₄ in acidic medium,
3. Pyridinium chlorochromate,
4. Heat in the presence of Cu at 573 K.
(a) 1, 3, 4
(b) 1, 3
(c) 1, 4
(d) none of the above
Answer:
(a)
Hint: KMnO₄ will oxidise the aldehyde formed to carboxylic acid.

16. Assertion: Bond angles in ethers is slightly more than the tetrahedral angle.
Reason: There are repulsions between two bulky ‘R’ groups.
(a) Assertion and reason both are correct, and reason is the correct explanation of assertion.
(b) Assertion and reason both are correct, but reason is not the correct explanation of assertion.
(c) Assertion is wrong, but reason is correct.
(d) Both assertion and reason are wrong.
Answer:
(c)
Hint: Correct assertion: Bond angles in ethers are slightly more than the tetrahedral bond angle.

17. Assertion: Bromination of benzene does not require Lewis acid is catalyst.
Reason: Lewis acid polarises the bromine molecule in Friedel craft’s reaction.
(a) Assertion and reason both are correct, and reason is the correct explanation of assertion.
(b) Assertion and reason both are correct, but reason is not the correct explanation of assertion.
(c) Assertion is true, but reason is wrong.
(d) Both assertion and reason are wrong.
Answer:
(b)

18. Match the entries in column I with appropriate entries in column II and choose the correct option using the codes given:



Answer:
(b)

19. Match the entries in column I with appropriate entries in column II and choose the correct option using the codes given:


Answer:
(d)

20. In the following sequence of reactions,

(a) CH₃CH₂CH₂OH
(b) CH₃CH(OH)CH₃
(c) CH₃CH₂CH₂CH₂OH
(d) (CH₃)₃CCH₂OH
Answer:
(b)
Hint: Since alkenes give Markovnikoff addition products, therefore 1° alcohols (a), (c) and (d) cannot be obtained by hydration. Thus, ‘Z’ is 2-propanol.
i.e.

21. Consider the following reaction:

The compound ‘Z’ is:
(a) CH₃CH₂OCH₂CH₃
(b) CH₃CH₂OSO₃H
(c) CH₃CH₂OH
(d) CH₂=CH₂
Answer:
(c)
Hint:

22. Formation of tert-butyl ether by reaction of sodium tert-butoxide and methyl bromide involves:
(a) elimination reaction
(b) electrophilic addition reaction
(c) nucleophilic addition reaction
(d) nucleophilic substitution reaction
Answer:
(d)

23.

Answer:
(a)

24. The red coloured compound formed during Victor-Meyer’s test is:

Answer:
(b)
Hint:

25. Following compounds are given:
(i) CH₃CH₂OH
(ii) CH₃COCH₃
(iii) CH₃CH(OH)CH₃
(iv) CH₃OH
Which of the above compounds on being warmed with iodine solution andNaOH, will give iodoform?
(a) (i), (iii) and (iv)
(b) only (i)
(c) (i), (ii) and (iii)
(d) (i) and (ii)
Answer:
(c)
Hint: Compounds containing CH₃CO group or CH₃CH(OH) group on warming with I₂ and NaOH will form iodoform. Hence, (i), (ii) and (iii) will give iodoform.