When a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydro-gens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not. −ODD2O CH3CHO CD3CH

When a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydro-gens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not. −ODD2O CH3CHO CD3CH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.4: Substituent Effects In Electrophilic Substitutions

Problem 11P

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Question

When a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydro-
gens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not.

−OD
D2O CH3
C
H
O

CD3
C
H

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