Alkylation of α carbon is more favored when the alkyl halide is primary and not when alkyl halide is tertiary. Concept introduction: Alkylation of α carbon atom in a carbonyl compound proceeds via the S N 2 mechanism. The S N 2 reaction involves only one step in which the carbonyl compound and alkyl halide combine to form a transition state. If the alkyl halide is bulky the transition state cannot be formed due to steric hindrance and instead an elimination product is formed.

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Chapter 13.4, Problem 11P

Interpretation Introduction

Interpretation:

Alkylation of α carbon is more favored when the alkyl halide is primary and not when alkyl halide is tertiary.

Concept introduction:

Alkylation of α carbon atom in a carbonyl compound proceeds via the SN2 mechanism. The SN2 reaction involves only one step in which the carbonyl compound and alkyl halide combine to form a transition state. If the alkyl halide is bulky the transition state cannot be formed due to steric hindrance and instead an elimination product is formed.

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