UNIT–11

ALDEHYDES, KETONES &CARBOXYLIC ACIDS

1. Write the IUPAC name of CH2=CHCOCH2COOH.
Ans: 3-Oxopent-4-en-oic acid.
2. p-Nirobenzoic acid has lower pKa value than benzoic acid. Why?
Ans: Nitro group is an electron withdrawing group so it increases the acidic
strength of p-Nitrophenol, hence pKa value is lower.
3. Arrange the following in the increasing order of their property indicated:
(a) CH3CHO, C6H5CHO, HCHO (reactivity towards nucleophilic addition)
(b) 2,4-dinitrobenzoic acid, 4-methoxybenzoic acid, 4-nitobenzoic acid (acidic)
Ans: (a) C6H5CHO < CH3CHO < HCHO
(b) 4-methoxybenzoic acid < 4-nitobenzoic acid < 2,4-dinitrobenzoic acid
4. Convert: (a) Ethanal to Propanone (b) Toluene to Benzoic acid
Ans: Hint - (a) CH3MgCl, H2O / H+, Cu /573K
(b) Alk. KMnO4, HCl
5. Give reasons for the following:
(a) Chloroacetic acid is more acidic than acetic acid.
(b) Aldehydes are more reactive than ketones towards nucleophilic attack.
(c) Formaldehyde does not respond to aldol condensation.
Ans: (a) due to –I effect, (b) due to less steric hinderance,
(c) due to absence of α-hydrogen
6. Write the structure of A and B in the following route charts:
(a) CH3COCl ⎯H⎯ ⎯⎯ ⎯→ A ⎯⎯
2 / Pd − BaSO4
⎯→ B
NH 2 OH

(b) CH3MgBr ⎯(⎯ ⎯⎯⎯→ A ⎯PCl

i ) CO 2 ( ii ) H 3O +
⎯→
⎯5 B
Ans: (a) A = CH3CHO, B = CH3CH=N–OH
(b) A = CH3COOH, B = CH3COCl
7. An aromatic organic compound -A(C8H8O) gives positive DNP test and Iodoform
test. It neither reduces Tollen’s reagent nor Fehling’s solution. Predict the
structure of ‘A’.
Ans: A = C6H5COCH3
8. Write the equations for the following: (a) Etard’s reaction
(b) Wolf-Kishner reduction
(c) HVZ reaction
Ans: Correct equations (see text book)
9. Give a chemical test to distinguish the following:
(a) Ethanal and Propanal
(b) Benzaldehyde and Acetophenone
(c) Pentan-2-one and Pentan-3-one
Ans: (a) Iodoform test;
Ethanal responds to Iodoform test but Propanal does not.
(c) Tollen’s test;
Benzaldehyde responds to Tollen’s test but Acetophenone does not.
(d) Iodoform test;
Pentan-2-one responds to Iodoform test but Pentan-3-one does not.
10. Account for the following:
(a) Benzoic acid does not give Friedel-Crafts reaction.
(b) The α-Hydrogen atoms of aldehydes and ketones are acidic in nature.
(c) Carboxylic acids do not give characteristic reactions of Carbonyl group.
Ans:
(a) In benzoic acid, carboxylic group is deactivating and it combines with Friedel-
Crafts catalyst anhy.AlCl3.
(b) It is because after losing H+, the carbanion is stabilized by resonance.
(c) It is because the carbonyl group in carboxylic acids involves in resonance.

MODEL QUESTIONS
1. What is formalin? Write one use of it.
2. Draw the structure of 4-Methylpent-3-en-2-one.
3. How will you distinguish between phenol and benzoic acid?
4. Branched carboxylic acids are less acidic than unbranched. Give reason.
5. Arrange the following in the increasing order of their boiling points:
 CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH2CH3
6. Illustrate the following:
(a) Rosenmund’s reduction
(b) Gatterman Koch reaction
7. Write the equations for the following conversions:
(a) Toluene to Benzaldehyde
(b) Acetic acid to Ethanamine
8. Account for the following:
(a) Formaldehyde responds to Cannizzaro’s reaction but not acetaldehyde.
(b) Carboxylic acids do not show characteristic reactions of carbonyl
compounds.
9. Write a chemical test to distinguish beween:
(a) Acetaldehyde and Acetone
(b) Formic acid and Acetic acid
10. Give reasons:
(a) Aldehydes are more reactive than ketones towards nucleophilic reactions.
(b) Most of the aromatic acids are solids but aliphatic acids are liquids.
11. Complete the following equations:
(a) CH3– C≡C – H HgSO / H SO
⎯⎯⎯4⎯⎯2⎯⎯
4→

K MnO / H SO
(b) ⎯⎯⎯⎯
4 ⎯⎯
2⎯⎯
4→

(c) C6H5CHO + conc. NaOH ⎯

⎯→

12. Write equations for the following:

(a) Benzaldehyde reacts with conc. NaOH .
(b) Acetone treated with dilute Ba(OH)2.
(c) Acetic acid is heated with Ammonia.
13. An organic compound with molecular formula C9H10O forms 2,4-DNP
derivative, reduces Tollen’s reagent and undergoes Cannizzarro’s rection. On
vigorous oxidation it gives 1,2-Benzenedicarboxylic acid. Identify the compound
and write the chemical equations.
14. Convert the following not more than two steps:
 (a) Propanone to Propene
(b) Ethanol to 3-Hydroxybutanal
(c) Benzene to m-Nitroacetophenone
15. Give a simple chemical test to distinguish between the following:
(a) Phenol and Benzoic acid
(b) Propanal and Propanone
(c) Acetophenone and Benzophenone
16. (a) illustrate the following named reactions:
(i) Clemmensen reduction
(ii) Hell Volhard Zelinsky reaction
(b) An organic compound A having molecular formula C8H16O2 was hydrolysed
with dilute sulphuric acid to a carboxylic acid B and an alcohol C. oxidation of C
with chromic acid produced B, C on dehydration gives but-1-ene. Write equations
for the reactions involved.

ASSERTION – REASON TYPE QUESTIONS

In these questions, a statement of assertion followed by a statement of reason
is given. Choose the correct answer out of the following choices.
1. Assertion: Benzoic acid is a weaker acid than formic acid.
Reason: Phenyl group destabilizes the carboxylate anion due to conjugation.
2. Assertion: Carboxylic acids do not give characteristic of carbonyl group.
Reason: The carbonyl group is sterically hindered in carboxylic acid.
3. Assertion: Carboxylic acids of lower molecular mass are water soluble.
Reason: Carboxylic acids of lower molecular mass are hydrogen bonded with
molecules of water.
4. Assertion: Formic acid reduces mercuric chloride to mercurous chloride on
heating while acetic acid does not.
Reason: Formic acid is a stronger acid than acetic acid.
5. Assertion: Aromatic aldehydes and formaldehyde undergo Cannizzaro reaction.
Reason: Aromatic aldehydes are almost as reactive as formaldehyde.
6. Assertion: Carboxylic acids contain a carbonyl group but do not give the
characteristic reactions of the group.
Reason: The electrophilicity of the carbon atom is more in carboxylic acids than
in aldehydes and ketones.
7. Assertion: When ethanol is treated with Fehling’s solution, it gives a red ppt.
Reason: Fehling’s solution is reduced by aldehydes to gives a red ppt. of Cu2O.
8. Assertion: The boiling points of aldehydes and ketones are higher than
hydrocarbons and ethers of comparable molecular masses.
Reason: Aldehydes and ketones undergo intermolecular association due to
dipole- dipole interactions.
9. Assertion: pka of acetic acid is lower than that of phenol.
Reason: Phenoxide ion is more resonance stabilized than acetate ion.

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 UNIT–12
ORGANIC COMPOUNDS CONTAINING NITROGEN (AMINES)

1. Ethyl amine is soluble in water but aniline is almost insoluble. Give reason.
Ans: Ethyl amine can form H-bonds with water molecules but aniline cannot due
to larger hydrocarbon part (hydrophobic)
2. Why are diazonium salts of aromatic amines are more stable than aliphatic
amines?
Ans: It is because aromatic diazonium salts are stabilized by resonance.
3. Arrange the following in the decreasing order of basic strength:
(i) C6H5NH2, CH3NH2, (CH3)2NH, (CH3)3N, NH3
(ii) C6H5NH2, C2H5NH2, (C2H5)2NH, (C2H5)3N, NH3
Ans: (i) (CH3)2NH < CH3NH2 < (CH3)3N < NH3 < C6H5NH2
(ii) (C2H5)2NH < (C2H5)3N < C2H5NH2 < NH3 < C6H5NH2,
4. Gabriel phthalimide synthesis is not preferred for aromatic primary amines. Why?
Ans: It is because aryl halides do not undergo nucleophilic substitution.
5. Write the equations for the following:
(a) Coupling reaction (b) Acylation of aniline (c) Carbylamine reaction
Ans: Correct equations (see text book)
6. An aromatic compound ‘A’on heating with Br2 and KOH forms a compound ‘B’
of molecular formula C6H7N, which on reacting with CHCl3 and alc.KOH
produces a foul-smelling compound ‘C’. Write the structure and IUPAC name of
A, B and C.
Ans: A = C6H5CONH2, Benzamide
B = C6H5NH2, Benzenamine
C = C6H5NC, Isocyanobenzene
7. Predict the structure of the products in the following:
CH3COOH ⎯⎯ ⎯→ A ⎯Br
NH 3 / 
⎯2 /⎯ ⎯→ B ⎯CHCl
aq. KOH
⎯⎯ ⎯⎯→ C
3 / alc. KOH

Ans: A = CH3CONH2, B = CH3NH2, C = CH3NC

8. Convert: (i) Nitrobenzene to Aniline
(ii) Ethanoic acid to Methanamine
 (iii) Aniline to N-Phenylethanamide
Ans: Hints (i) Sn / HCl (ii) NH3 / Δ, Br2 / KOH (iii) CH3COCl
9. Give a chemical test to distinguish between the following:
(a) Phenol and Aniline
(b) Ethyl amine and Aniline
(c) Methyl amine and Dimethyl amine
Ans: (a) Azodye test (b) Coupling test / Azodye test (c) Hinsberg’s reagent
10. Give reasons for the following:
(a) Aniline does not undergo Fridel Crafts reaction
(b) Secondary amines are more basic than tertiary amines
(c) Primary amines have higher boiling point than tertiary amines.
Ans: (a) Aniline is a Lewis base and it forms an adduct with anhy.AlCl3(Lewis acid)
(b) Steric hinderance is less in secondary amines.
(c) It is due to formation of intermolecular H-bonds with water molecules.

MODEL QUESTIONS
1. Which compounds are known as carbylamines?
2. Write the IUPAC name of the compound CH3CH2CH2N(CH3)2.
3. Why aliphatic amines are more basic than ammonia?
4. Ethylamine is soluble in water but not aniline. Give reason.
5. Arrange the following in the decreasing order of their basic strengths:
C6H5NH2, C2H5NH2, (C2H5)2NH and NH3
6. Give a chemical test to distinguish between:
(a) Aniline & Ethyl amine
(b) Methyl amine & dimethyl amine
7. Complete the following:
(a) CH3NH2 + HNO2 →
(b) C6H5NH2 + conc. H2SO4 →
8. Identify A, B, C and D in the following route chart:
+KOH
CH3CH2I NaCN
⎯⎯⎯
⎯→ A OH − / partialhydrolysis
⎯⎯⎯⎯⎯⎯⎯⎯
⎯→ B NaOH + Br
⎯⎯ ⎯ ⎯⎯2
→ C ⎯CHCl
⎯⎯ 3
⎯
⎯→ D.
9. Write the structures of all isomers of the compound C3H9N. Which isomer will
liberate nitrogen gas on treatment with nitrous acid?
10. Give reasons:
(a) Tertiary amine do not undergo acylation.
(b) Methyl amine in water produces red ppt. with ferric chloride.
11. Illustrate the following named reactions:
(a) Carbylamine reaction
(b) Gabriel phthalimide reaction
(c) Hoffmann’s degradation reaction
12. Convert:
(a) Aniline to 1, 3, 5-tribromobenzene.
(b) Benzene to m-bromophenol.
(c) Benzyl chloride to 2-Phenyl ethanamine.
13. Give reasons:
(a) Aniline does not undergo Friedel-Crafts reaction
(b) pKb of aniline is more than that of methylamine
(c) Primary amines have higher boiling point than tertiary amines.
14. Write chemical equations for the following:
(a) Ethanamide is heated with P2O5
(b) Aniline is treated with NaNO2 and HCl at 273K.
(c) Methyl amine is treated with benzene sulphonyl chloride.
15. Complete the following equations:
(a) C2H5NH2 + HNO2 →
(b) C6H5NH2 + CH3COCl →
(c) CH3NH2 + CHCl3 + KOH →
16. Explain with reason.
(a) Aniline is less than methyl amine
(b) Gabriel phthalimide reaction is only meant for primary aliphatic amines.
17. An aromatic compound ‘A’ on treatment with aqueous NH3 and heating forms
compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’ of
molecular formula C6H7N. Write the structures and write the equations involved.

ASSERTION – REASON TYPE QUESTIONS

1. Assertion: Aniline on reaction with NaNO2/HCl followed by coupling with
phenol in basic medium gives a blue colour ppt.
Reason: The colour of the compound formed in the reaction is due to extended
conjugation.
2. Assertion: The diazonium salts of aromatic amines are more stable than those of
the aliphatic amines.
Reason: The N2+Cl group is a meta directing and deactivating group.
3. Assertion: When the temp. of the diazonium salt solution is allowed to rise above
278K, the salt is hydrolysed to form phenol
Reason: Aryl diazonium salts are highly soluble in water.
4. Assertion: The benzene diazonium chloride reacts with CuCN/KCN to form
cyanobenzene which is hydrolysed in acidic medium to form benzoic acid
Reason: The reaction involves retention of diazo group.
5. Assertion: Ammonolysis of alkyl halides is not a suitable method for preparation
of pure primary amines.
Reason: Ammonolysis of alkyl halides yields mainly tertiary amines.
6. Assertion: Aniline does not undergo Friedel -Crafts reaction.
Reason: Friedel –Crafts reaction is an electrophilic substitution reaction.
7. Assertion: Ethylamine is soluble in water whereas aniline is not.
Reason: Ethylamine dissolves in water due to intermolecular H- bonding.
8. Assertion: Amines are more basic than esters and ethers.
Reason: Nitrogen is less electronegative than oxygen. It is a better position to
accommodate the positive charge on the proton.
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 UNIT–13
BIOMOLECULES

1. Name the water soluble vitamin which is a powerful antioxidant.

Ans: Vitamin-C
2. What is the difference between nucleotide and nucleoside?
Ans: Nucleoside contains deoxyribose sugar, heterocylic base. Whereas
Nucleotide contains phosphoric acid along with pentose sugar and heterocyclic
base.
3. What are the hydrolysis products of lactose?
Ans: glucose and galactose
4. What happens when D-glucose is treated with (a) HI and (b) conc. HNO3?
Ans: (a) n-Hexane is formed (b) Saccaric acid is formed
5. Differentiate: Peptide linkage and Glycosidic linkage
Ans: In proteins, different α-amino acids are joined by amide (-CONH-) bonds by
the loss of water molecules, such an amide bond is called peptide linkage.
In disaccharides, two monosaccharide units are joined by oxide linkage by the loss
of water molecule, such an oxide linkage is called glycosidic linkage
6. Define: (a) Anomers (b) Denaturation of proteins
Ans:
Anomers: The carbohydrates which differ in orientation of –OH group on C-
1carbon atom are called anomers. Eg.α-glucose and β-glucose.
Denaturation of proteins: When proteins in its native state are subjected to change
in pH or temperature then H-bonds gets disturbed, globules unfold, helix get
uncoiled and proteins lose their biological activity. This is known as denaturation
of proteins.
7. Name the type of bonding which stabilises alpha-helix in proteins.
Ans: Intra-molecular H-bonding.
8. Answer the following: (a) What type of linkage is present in disaccharides?
(b) Which disease is caused by deficiency of vitamin-B12?
 Ans: (a) glycosidic linkage (b) anaemia
9. What is glycogen? How it is different from starch?
Ans: Carbohydrates are stored in the animal body in the form of glycogen,
whereas carbohydrates are stored in the plant body in the form of starch.
10. What are essential and non-essential amino acids? Give example.
Ans: The amino acids which are not synthesized in the body and must be obtained
through diet are known as essential amino acids. Eg.Valine.
The amino acids which are synthesized in our body are known as non-essential
amino acids. Eg. Glycine.

MODEL QUESTIONS
1. Why are carbohydrates generally optically active?
2. What happens when glucose is treated with bromine water?
3. What happens when glucose reacts with nitric acid?
4. Write a reaction which shows that all the carbon atoms in glucose are linked in
straight chain.
5. How do you explain the presence of five – OH groups in glucose molecules?
6. What are reducing sugar? Give one example of it.
7. Write the reactions involved when D- glucose is treated with the following
reagents: (i) HCN (ii) NH2OH
8. What is meant by the following :
(a) Peptide linkage (b) Glycosidic linkage
9. (i) What type of linkage is present in nucleic acid?
(ii) Give one example of each for fibrous protein and globular protein.
10. What are essential and non-essential amino acids?
11. What are α-amino acids? How are they related to proteins? Give the structure of
one α-amino acid.
12. Name the bases present in RNA. Which one of these is not present in DNA?
13. Give three differences between RNA and DNA.
14. Give reasons for the following statements:
 (i) Amino acids are amphoteric in nature.
(ii) Amino acids have comparatively higher M.P. than the corresponding halo
acids.
15. (a) What is the difference between native protein and denatured protein?
(b) Which one of the following is a monosaccharide: Maltose, fructose, starch.
(c) Name a base present in DNA.
(d) Define the following terms: (i) Native protein (ii) Nucleotide

ASSERTION – REASON TYPE QUESTIONS

1. Assertion: Sucrose is a non-reducing sugar.
Reason: It has glycosidic linkage.
2. Assertion: Glocose and fructose can be distinguished by Tollen’s reagent.
Reason: Glucose contains aldehydic group while fructose contains a keto group.
3. Assertion: Carbohydrates were earlier called as hydrates of carbon.
Reason: Carbohydrates can be hydrolysed.
4. Assertion: Starch is a non-sugar.
Reason: Starch is polysaccharides.
5. Assertion: D(+) –glucose is dextrorotatory in nature.
Reason: ‘D’ represents its dextrorotatory nature.
6. Assertion: β-glycosidic linkage is present in maltose.
Reason: Maltose is composed of two glucose units in which C-1 of one glucose
unit is linked to C-4 of another glucose unit.
7. Assertion: Glycine must be taken through diet.
Reason: It is a non-essential amino acid.
8. Assertion: Glucose does not react with ammonia.
Reason: NH3 is a Lewis base.
9. Assertion: Reducing sugars undergo mutarotation.
Reason: During mutarotation, one pure anomer is converted into an equilibrium
mixture of two anomers.
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