Chapter 9, Problem 9.71P

Interpretation Introduction

Interpretation:

The mechanism for the given overall reaction is to be drawn.

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 then evaluate the type of carbon bonded to the leaving group. For the ${\text{S}}_{\text{N}}{\text{1, S}}_{\text{N}}\text{2, E1, or }\text{}\text{E2}$ 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. And 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 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 solvent. If both substitution and elimination reactions appear to be favored, then factor in the influence is heat. Intramolecular reactions are the ones in which two functional groups are at different places on the molecule’s backbone.