The correct structure of product 'A' formed in the following reaction. $\ce{PhCHO + Ph·CHO ->[NaOD][in D2O] A + Ph-\overset{O}{C}-O^-}$ (Ph is $-\ce{C6H5}$)

JEE Main · 2022 · 28 Jun 2022 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

The correct structure of product 'A' formed in the following reaction.

PhCHO + Ph \cdot CHO NaOD in D X_{2} O A + Ph - C O - O X^{-}

(Ph is

- C X_{6} H X_{5}

)

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

This is a Cannizzaro reaction in deuterated medium. Two molecules of benzaldehyde undergo disproportionation in the presence of

NaOD

D X_{2} O

. One molecule is reduced to benzyl alcohol (with deuterium incorporated) and the other is oxidized to benzoate ion. The product A is

PhCH X_{2} OD

(benzyl alcohol with deuterium on the oxygen).

JEE Main · 2022 · 28 Jun 2022 · Shift 1 · Single correct option

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