Chapter 13, Problem 13.1YT

Interpretation Introduction

(a)

Interpretation:

The synthetic step that shows $\text{2-phenyl-2-tosyloxypropane}$ reacting with NaCl to produce $\text{2-chloro-2-phenylpropane}$ is to be written.

Concept introduction:

A synthetic step is written with just the overall reactants, the added reagents, the reaction conditions, and the overall products. The details of how the reactants and reagents actually react are not included. The reaction conditions may include the solvent, any catalysts (acid/base) used, and the temperature.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the reaction from part (a) is to be drawn.

Concept introduction:

The mechanism shows the actual elementary steps that must occur for the reactants to be transformed into the products. The mechanism may contain more than one elmentary step.

Each mechanism depends mainly on the nature of the substrate and the incoming nucleophile. The solvent may also play a role by stabilizing the leaving group and/or stabilizing a possible intermediate.

If the leaving group is present in a secondary or tertiary position and is a stable, good leaving group, it favors the two-step ${\text{S}}_{\text{N}}\text{1}$ mechanism. A nucleophile that is not a strong base and is a poor or moderately good nucleophile also favors ${\text{S}}_{\text{N}}\text{1}$ mechanism.