(a) Although phenoxide ion has more number of [5] resonating structures than Carboxylate ion, Carboxylic acid is a stronger acid than phenol. Give two reasons.
(b) How will you bring about the following conversions?
(i) Propanone to propane
(ii) Benzoyl chloride to benzaldehyde
(iii) Ethanal to but-2-enal
OR
(a) Complete the following reactions:
(i) 
(ii)![]()
(iii)
(b) Give simple chemical tests to distinguish between the following pairs of compounds: ‘
(i)Ethanal and Propanal
(ii)Benzoic acid and Phenol
(a) Although phenoxide ion has more number of [5] resonating structures than Carboxylate ion, Carboxylic acid is a stronger acid than phenol. This is due to the formation of equivalent resonance structures for carboxylate ion and this lacks for phenoxide ion.
In carboxylate ion the negative charge is effectively delocalized over two oxygen atoms whereas it is less effectively delocalized over one oxygen atom and less electronegative carbon atom.

Resonance structures of phenoxide ion

Resonance structures of carboxylate ion
(b)
(i) If propanone is reduced Zinc amalgam in HCl, we get propane. This process is called Clemmensen Reduction.

(ii) When benzoyl chloride is treated with H2 and poisoned Pd in BaSO4, it is reduced to benzaldehyde.

(iii) Ethanal is converted to but-2-enal by a process called aldol condensation.
First aldol of ethanol is done by treating it with NaOH, that is we get 3-hydroxybutanal which on condensing gives but-2-enal.

OR
(a)
(i) Since formaldehyde has no α Hydrogen, Cannizaro reaction takes place thereby forming methanol and potassium formate.

(ii) CH3COOH under Br2 and red Phosphorus gives α-bromoacetic acid. This reaction is called HVZ (Hell-Volhard-Zelensky) reaction.

(b)
(i) Ethanal and Propanal
Aldehydes and ketones having at least one methyl group linked to the carbonyl carbon atom responds to the iodoform test. Ethanal having one methyl group linked to the carbonyl carbon atom responds to this test. But propanal does not have a methyl group linked to the carbonyl carbon atom and thus, it does not respond to this state.

(ii) Benzoic acid and Phenol
Phenol reacts with neutral FeCl3 to form an iron-phenol complex giving violet colouration.

But benzoic acid reacts with neutral FeCl3 to give a buff coloured ppt. of ferric benzoate.

Couldn't generate an explanation.
Generated by AI. May contain inaccuracies — always verify with your textbook.