Chapter 13, Problem 13.12P

Interpretation Introduction

Interpretation:

How $\text{3, 4-dimethylhex-2-ene}$ can be synthesized via two different precursors, with the leaving group on C2 or on C3, is to be shown.

Concept introduction:

In a retrosynthetic analysis, the position and the substitution of the double bond in the product must be taken into account when determining the precursor. The substituents on the double bond and on the adjacent carbon atoms determine if the product is a Zaitsev product or a Hofmann product. This, in turn, will determine the position and nature of the leaving group and the nature of the base.