Chapter 6, Problem 20P

Interpretation Introduction

Interpretation:

By analogy about nucleophilic substitution reactions in simple systems, the product for each of the given reactions is to be predicted.

Concept introduction:

Primary alkyl halide undergoes predominantly ${\text{S}}_{\text{N}}\text{2}$ reactions regardless of the basicity of nucleophiles. ${\text{S}}_{\text{N}}\text{2}$

reaction is a one-step concerted process. The rate of reaction depends on both reactants, that is, substrate and nucleophile. The nucleophile approaches from the opposite side to the leaving group.

Generally, it is true that the less basic the leaving group, the smaller the energy requirement for cleaving its bond to carbon and the faster the rate. Thus, good leaving groups are weak bases.

Primary alkyl chlorides react with sodium acetate to yield the corresponding acetate esters.

Hydrolysis of alkyl halides yields corresponding alcohols.

Alkyl sulfonates are derivatives of sulfonic acids prepared by treating an alcohol with the appropriate sulfonyl chloride, usually in the presence of pyridine. Alkyl sulfonates undergo nucleophilic substitution similar to alkyl halides.