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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 :

A
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B
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C
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D
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Solution

The correct option is C
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 same compound on reaction with conc. NaOH forms benzyl alcohol as one of the products, This shows that the compound undergoes cannizzaro reaction. One molecule is reduced to alcohol and other molecule is oxidized to carboxylate ion. Hence, option (c) is correct.

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