A compound of molecular formula \(\mathrm{C_8H_8O_2}\) reacts with acetophenone to form a single cross-aldol product in the presence of base. The same compound on reaction with conc. NaOH forms benzyl alcohol as one of the products. The structure of the compound is :
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The Correct Option is A
Solution and Explanation
A single cross-aldol product with acetophenone requires an aldehyde with no \(\alpha\)-hydrogen (it can act only as the electrophile). Conc. NaOH giving a benzyl alcohol type product is a Cannizzaro reaction, which also needs an aldehyde without \(\alpha\)-H.
Option (1), 4-methoxybenzaldehyde \(\mathrm{CH_3O-C_6H_4-CHO}\) (\(\mathrm{C_8H_8O_2}\)), fits both.
Option (2) is an enolisable ketone (and a phenol); option (3) is an ester and option (4) a carboxylic acid; none of these gives a cross-aldol or Cannizzaro product.
Answer: (1) 4-methoxybenzaldehyde
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