Which of the following undergo an intramolecular Cannizzaro reaction (one carbonyl carbon is oxidised and another reduced within the same molecule) on treatment with concentrated NaOH? (One or more answers)

Aethanedial, $OHC - CHO$
Bphenylglyoxal, $C X_{6} H X_{5} COCHO$
Chexanedial, $OHC (CH X_{2}) X_{4} CHO$
Dbutane-2,3-dione, $CH X_{3} COCOCH X_{3}$

Answer: A, B

Intramolecular Cannizzaro needs adjacent carbonyls with a CHO and no alpha-hydrogen. Ethanedial and phenylglyoxal both qualify and give hydroxy acids. Hexanedial has alpha-hydrogens and cyclises by aldol condensation. Butane-2,3-dione has no CHO and is not a Cannizzaro substrate.

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Which of the following undergo an intramolecular Cannizzaro reaction (one carbonyl carbon is oxidised and another reduced within the same molecule) on treatment with concentrated NaOH? (One or more answers)

Answer: A, B

More questions on Aldol, Cannizzaro, Perkin, Claisen and related condensations