DOHA MODERN INDIAN SCHOOL
Aldehydes, Ketones & Carboxylic Acids- Give Reasons
1. Aldehydes are more reactive than ketones towards nucleophiles.
Ans: This is due to steric and electronic reasons. Sterically, the presence of two
relatively large substituents in ketones hinders the approach of nucleophile to
carbonyl carbon than in aldehydes having only one such substituent. Electronically
two alkyl groups reduce the positivity of the carbonyl carbon more effectively in
ketones than in aldehydes.
2. The boiling points of aldehydes and ketones are lower than of the corresponding
acids.
Ans: This is due to intermolecular hydrogen bonding in carboxylic acids.
3. The aldehydes and ketones undergo a number of addition reactions.
Ans: Due to greater electronegativity of oxygen than carbon the C atom of the C =
O bond acquires a partial positive charge in aldehydes and ketones and hence
readily undergo nucleophilic addition reactions.
4. Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-
trimethylcyclohexanone does not.
Ans: Due to presence of three methyl groups, the nucleophilic attack by CN– ion
does not occur due to steric hindrance in 2, 4, 6-trimethyl cylcohexanone. As there
is no such steric hindrance in cyclohexanone so nucleophilic attack by the CN– ion
occurs readily and hence cyclohexanone cyanohydrin is obtained in good yield.
5. Ethanal is more reactive than acetone towards nucleophilic addition reaction.
Ans: This is due to steric and electronic reasons. Sterically, the presence of two
relatively large substituents in ketones hinders the approach of nucleophile to
carbonyl carbon than in aldehydes having only one such substituent. Electronically
two alkyl groups reduce the positivity of the carbonyl carbon more effectively in
ketones than in aldehydes.
6. (CH3)3C—CHO does not undergo aldol condensation.
Ans: This is because for aldol condensation to take place, at least one a-hydrogen
(i.e., hydrogen at carbon adjacent to carbonyl carbon) should be available, which is
not present in (CH3)3C—CHO.
7. Carboxylic acids are higher boiling liquids than alcohols.
Ans: This is due to more extensive association of carboxylic acid molecules
through intermolecular hydrogen bonding. The hydrogen bonds do not break
completely even in the vapour phase.
8. CH3CHO is more reactive than CH3COCH3 towards reaction with HCN.
Ans: The methyl group due to its +I effect reduce the magnitude of positive charge
on carbonyl carbon atom. Moreover, it also hinders the approach of nucleophile
CN-. Since in acetaldehyde there is one methyl while in acetone there are two
methyl groups attached to carbonyl group therefore acetaldehyde is more reactive
than acetone towards nucleophilic addition with HCN.
9. Carboxylic acid is a stronger acid than phenol.
Ans: Because the release of proton from carboxylic acid is much easier than from
phenol as the conjugate base carboxylate ion is much more resonance stabilised
than conjugate base phenoxide ion.
10.Arrange the following compounds in an increasing order of their acid strengths:
(CH3)2CHCOOH, CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH
Ans: (CH3)2CHCOOH, CH3CH(Br)CH2COOH, CH3CH2CH(Br)COOH
11.Arrange the following compounds in an increasing order of the acid strength:
Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-
Methoxybenzoic acid
Ans: 4-Methoxy benzoic acid <Benzoic acid < 4-Nitrobenzoic acid < 3, 4-
Dinitrobenzoic acid.
12.Arrange the following compounds in increasing order of their reactivity towards
nucleophilic addition reaction
CH3COCH3, C6H5—CO—C6H5, CH3CHO
Ans: C6H5COC6H5< CH3COCH3 < CH3CHO
