Chapter 11, Problem 11.28P

Interpretation Introduction

Interpretation:

Treatment of $\text{(R)-4-chlorocyclohexane}$ with $\text{HCl}$ produces a mixture of four products. The mechanism showing the formation of all four products is to be drawn, and it is to be identified which products are optically active.

Concept introduction:

The electrophilic addition of ${\text{H}}^{\text{+}}$ to the C=C double bond produces carbocation intermediate. In the next coordination step, the nucleophile attacks the positively charged ${\text{C}}^{\text{+}}$ carbon atom.

The carbocation intermediate is a trigonal planar, and the nucleophile can attack the ${\text{C}}^{\text{+}}$ from the front (wedge) or from behind (dash). This leads to different products. The position of substituents at other carbons in the substrate remains unchanged.

The compound not having any symmetry element is the chiral compound.