The compound phenyl benzoate on reaction with NaOH solution will yield:
A. Phenol
B. Benzaldehyde
C. Benzoic acid
D. Benzophenone
Choose the correct answer from the options given below:
Answer & explanation
Correct answer: option 2
The correct answer is Option (2) → A and C only
Phenyl benzoate, \( \ce{C6H5COOC6H5} \), is the ester of benzoic acid and phenol. Hot sodium hydroxide hydrolyses the ester linkage (saponification): the acyl part becomes the carboxylate and the phenyl part becomes phenoxide.
\( \displaystyle \ce{C6H5COOC6H5 + 2NaOH} \xrightarrow{\Delta} \ce{C6H5COONa + C6H5ONa + H2O} \)
Acidification then gives benzoic acid and phenol:
\( \displaystyle \ce{C6H5COONa + HCl -> C6H5COOH + NaCl} \)
\( \displaystyle \ce{C6H5ONa + HCl -> C6H5OH + NaCl} \)
A. Phenol — Correct. The \( \ce{O-C6H5} \) part of the ester comes off as phenoxide, i.e. phenol.
B. Benzaldehyde — Incorrect. Hydrolysis does not reduce the carbonyl carbon; no aldehyde is formed.
C. Benzoic acid — Correct. The \( \ce{C6H5CO} \)– part ends up as sodium benzoate, i.e. benzoic acid.
D. Benzophenone — Incorrect. Benzophenone, \( \ce{C6H5COC6H5} \), would need a new C–C bond between the two rings; hydrolysis only breaks the C–O bond of the ester.
NCERT (2026-27 edition):
From Esters – “Acidic hydrolysis of esters gives directly carboxylic acids while basic hydrolysis gives carboxylates, which on acidification give corresponding carboxylic acids.”