Chapter 11.2, Problem 6P

Interpretation Introduction

Interpretation:

A reason behind the betteryield of the substitution product of $\text{trans-1-chloro-2-butene}$ than $\text{3-chloro-1-butene}$ is to be discussed.

Concept Introduction:

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Allyl chlorides have a chlorine atom attached on the carbon atom adjacent to $\text{C=C}$

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${\text{S}}_{\text{N}}\text{2}$ reactions of ally chlorides proceed mainly with substitution rather than elimination.

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A good nucleophile exclusively forms the substitution product.When the concentration of nucleophile is low, a mixture of products may be obtained since allyl rearrangements may take place.

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The reaction works best with primary unhindered allyl chlorides.