JEE Main Chemistry question

A benzene-1,2-dicarbaldehyde dimer-type substrate --(i) NaOH/100°C (ii) H⁺/H₂O--> major product. The major product is

(A)A lactone/lactol-type cyclized bis-hydroxyacidCorrect
(B)A simple diacid
(C)A simple diol
(D)An open bis-aldehyde

Answer: (A)

Solution

With no α-hydrogens available (an aromatic dialdehyde system), hot concentrated NaOH drives a Cannizzaro-type disproportionation at each aldehyde pair, converting –CHO groups to –CH₂OH/–COOH pairs; the resulting hydroxy-acid functionality on the biphenyl-type framework then favours intramolecular lactonization (the

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Question ID VK-149180