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Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

16. Conjugated Systems / Conjugated Hydrohalogenation (1,2 vs 1,4 addition) / Problem 1

Explain why cyanide undergoes 1,2-addition instead of 1,4-addition in the reaction given below.

ANSWERS OPTIONS

A

1,2-addition occurs instead of 1,4-addition because the given compound is not a straight-chain carbonyl compound.

B

1,2-addition occurs instead of 1,4-addition the given compound is not an α,β-unsaturated carbonyl compound.

C

1,2-addition occurs instead of 1,4-addition because cyanide is a very strong nucleophile.

D

1,2-addition occurs instead of 1,4-addition because an enolate is formed upon the addition of a nucleophile.

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