Chapter 9, Problem 9.33P

Interpretation Introduction

Interpretation:

The major product of the reaction between alkyl bromide and sodium methoxide in acetone is to be predicted.

Concept introduction:

In order to predict the outcome of a given reaction, four factors are considered.

First is to determine if the substrate molecule has a suitable leaving group. If the leaving group is suitable, evaluate the type of carbon bonded to the leaving group. For an ${\text{S}}_{\text{N}}{\text{1, S}}_{\text{N}}\text{2, E1, or }\text{}\text{E2}$ reactions to take place readily, the carbon atom needs to be ${\text{sp}}^3$ hybridized. If the leaving group is on a primary carbon atom, then ${\text{S}}_{\text{N}}\text{1, and E1}$ reactions are not feasible unless the resulting carbocation is resonance stabilized. If the leaving group is on a tertiary carbon atom, then ${\text{S}}_{\text{N}}\text{2}$ reactions are not feasible. Further, if it is attached to a secondary carbon atom, then all four reactions are equally likely. The next step is to examine the influence of the factors like the strength of the attacking species as a nucleophile and as a base, the concentration of the attacking species, the leaving group ability, and the effect of the solvent. If both substitution and elimination reactions appear to be favored, then factor in the influence is heat.