JEE Main 2017 · 9 Apr · Shift 1 · Chemistry Q51

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ChemistrySingle correct+4 / -1Question 51 of 90

A compound of molecular formula $\ce{C8H8O2}$ 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 :

4-Methoxybenzaldehyde

4-Hydroxyacetophenone

Methyl benzoate

4-Methylbenzoic acid

Answer and worked solution

Official answer: A

Forming benzyl alcohol (here 4-methoxybenzyl alcohol) with concentrated NaOH is the Cannizzaro reaction, so the compound is an aldehyde with no α-hydrogen. It can only act as the acceptor in a cross-aldol with acetophenone, giving a single product. $\ce{C8H8O2}$ fits 4-methoxybenzaldehyde.

Topics:Named reactions Aldol and related condensations

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JEE Main 2017 · 9 Apr · Shift 1, Chemistry question 51