REASONS FOR PROPERTIES OF ALDEHYDES, KETONES, CARBOXYLIC ACIDS
1 Aldehydes and Ketones have lower boiling points than corresponding alcohols due to weak
molecular association in aldehydes and ketones arising out of the dipole- dipole interactions
whereas in alcohols there is intermolecular hydrogen bonding
2 Ethanal is soluble in water due to H-bonding between the polar carbonyl group and water
molecules.
3 Carboxylic acids do not give characteristic reactions of carbonyl group. The carboxylic carbon is
less electrophilic than carbonyl carbon because of the possible resonance structure.
4 Carboxylic acids have higher boiling points then alcohols due to more extensive association of
carboxylic acid molecules through intermolecular hydrogen bonding. The hydrogen bonds are not
broken completely even in the vapour phase.
5 HCOOH does not give HVZ reaction because there is no alpha hydrogen while CH3COOH because
alpha substitution is possible
6 The large difference in the boiling point of butanol and butanal although they have same solubility
in water is due to intermolecular hydrogen bonding in Butanol
7 Methanal(Formaldehyde) and Benzaldehyde(Phenyl methanal) undergo Cannizaro reaction due to
the absence of alpha hydrogen atoms
8 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic
acid is a stronger acid than phenol as a carboxylate anion is stabilised by two equivalent resonance
structures in which the negative charge is at the more electronegative oxygen atom.
9 Cyclohexanone forms cyanohydrin in good yield because the ketonic group has very less steric
hindrance at both the ortho position but 2,2,6 tri methyl cyclohexanone does not as there is high
steric hindrance which reduces the attack from CN nucleophile.
10 4-Methoxy benzoic acid is less acidic due to the +I effect
of methoxy group whereas nitro group is electron
withdrawing with –I effect. So the acidic nature is in the
order
4 methoxy benzoic acid < Benzoic acid < 4 nitro benzoic
11 During the preparation of esters fromacid
a carboxylic acid and an alcohol in the presence of an
acid catalyst, the water or the ester should be removed as soon as it is formed in order to get
maximum yield by shifting equilibrium to forward direction (according to Le Chatlier
principle)
12 There are two –NH2 groups in semicarbazide. However, only one is involved in the
formation of semicarbazones. Due to resonance one NH2 group is involved in resonance
and hence does not participate in the formation of semicarhazone.
13 Propanal is more reactive than Propanone. Due to the presence of alkyl groups on both
sides of the carbonyl carbon, propanone is sterically more hindered than propanal. Both
methyl groups have an electron-releasing tendency due to the -I effect.
14 Electrophilic substitution in benzoic acid takes place at meta position as the — COOH
group in benzene is an electron withdrawing group, that is meta directing group.
15 Arrange the following compounds in the increasing order of their boiling points :
CH3OCH3 < CH3CHO < CH3CH2OH < CH3COOH.
16
Sodalime - decarboxylating agent
Decarboxylation:
17 Butanone < Propanone < Propanal < Ethanal(Reactivity in nucleophilic addition reaction)
18 CH3CH2CH3 < CH3CHO < CH3CH2OH (boiling points)
19 Propanol > Propanal > Propane (Boiling point)
20 C6H5COCH3 < CH3COCH3 < CH3CHO (Reactivity towards nucleophilic addition)
21 4-Methoxy benzoic acid < Benzoic acid < 4-Nitrobenzoic acid < 3, 4-Dinitrobenzoic
acid.(acid strength)
22
acid strength
23 Methyl tert-butyl ketone < Acetone < Acetaldehyde (reactivity towards HCN)
24 CH3OCH3 < CH3CHO < CH3CH2OH < CH3COOH(Boiling point)
Reactions in aldehydes, Ketones and Carboxylic acids
Write formula: (Ethyl 4 chloro benzoate), (4 chloro pentan-2-one), (pent–2-en-1-al), (but-2-enal), (1 phenyl
pentan-1-one), (but-2-enal), (pent-2-enal), (2 methyl but-2-enal), (pent-2-enal), (1 phenyl propan-1-one),
(4 methyl pent-3-en-2-one), (3 bromo 5 chloro benzoic acid), (3 oxo pentanal), (3 amino butanal)
(i) Ethanal, Propanal, Propanone, Butanone.(Nu Subs reaction order)
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
(iii) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone
