JEE Main 2022 · 28 Jun · Shift 1 · Chemistry Q74

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ChemistrySingle correct+4 / -1Question 74 of 90

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

$\mathrm{PhCHO+Ph\cdot CHO\xrightarrow[in\ D_2O]{NaOD}A+Ph{-}\overset{O}{\overset{\|}{C}}{-}O^-}\qquad(\mathrm{Ph\ is\ {-}C_6H_5})$

Ph-CH

_2

-OD

Benzyl alcohol-OD: carbon bearing Ph, OD, H and H.

Ph-CH

_2

-OH

Benzyl alcohol: carbon bearing Ph, OH, H and H.

Ph-CHD-OD

Ph-CD

_2

-OD

Answer and worked solution

Official answer: A

Cannizzaro in $\mathrm{D_2O}$ . The hydride moved to the second aldehyde comes from the C-H of the first (not the solvent), so the carbon gets two H. The alkoxide then takes $\mathrm{D^+}$ from $\mathrm{D_2O}$ : $\mathrm{PhCH_2OD}$ .

(A)

Topics:Named reactions

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JEE Main 2022 · 28 Jun · Shift 1, Chemistry question 74