In which of the following does the Birch reduction (Na, liquid NH3, ethanol) give a product in which every substituent sits on an sp2 carbon of the 1,4-diene?

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In which of the following does the Birch reduction (Na, liquid $NH X_{3}$ , ethanol) give a product in which every substituent sits on an sp2 carbon of the 1,4-diene?

Atert-butylbenzene
BN,N-dimethylaniline
Cbenzoic acid
D1,4-dimethylbenzene

Answer: A, B, D

Alkyl and amino groups are electron-donating and remain on the double bonds. In p-xylene both methyls sit on the carbons that keep their double bonds (reduction at C2 and C5). Benzoic acid places

COOH

on an sp3 carbon.

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In which of the following does the Birch reduction (Na, liquid NHX3​, ethanol) give a product in which every substituent sits on an sp2 carbon of the 1,4-diene?

Answer: A, B, D

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In which of the following does the Birch reduction (Na, liquid $NH X_{3}$ , ethanol) give a product in which every substituent sits on an sp2 carbon of the 1,4-diene?