Chapter 8, Problem 8.12YT

Interpretation Introduction

Interpretation:

Which of carbocations $\text{A - C}$ will undergo coordination with ${\text{I}}^{\text{-}}$ to produce a single product, an equal mixture of stereoisomers, or an unequal mixture of stereoisomers is to be determined.

Concept introduction:

The carbocation intermediate formed in ${\text{S}}_{\text{N}}\text{1}$ reaction is ${\text{sp}}^{\text{2}}$ hybridized, and its molecular geometry is trigonal planar, allowing for two different points of nucleophilic attack. The formation of stereoisomers depends on the stereochemical nature of carbocations.