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Question:

A compound of molecular formula C8H8O2 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 :

Solution:

A compound of molecular formula C8H8O2 reacts with acetophenone to form a single cross-aldol product in the presence of base. This shows that the compound does not contain α-hydrogen atom. The reaction with conc. NaOH forms benzyl alcohol, indicating the presence of a benzyl group. Considering these points, the structure of the compound is likely to be an ester, specifically benzyl benzoate. Benzyl benzoate does not have an α-hydrogen and upon reaction with conc. NaOH undergoes saponification to give benzyl alcohol and benzoic acid.