Chapter 12.16, Problem 17P

Interpretation Introduction

Interpretation:

The preparation of $\text{trans-2-phenylcyclopentanol}$ from cyclopentylbenzene by using retrosynthetic analysis is to be described and the equations are to be written showing suitable reagents for synthesis.

Concept introduction:

When aromatic compounds containing alkyl groups attached to them are treated with $\text{N-bromosuccinimide}$, benzylic bromides are obtained. This reagent specifically attaches a bromine atom at the benzylic position.

Alkyl halides, when treated with a strong base like ethoxide ion, undergo elimination reaction. The major product is the most substituted alkene.

Hydroboration-oxidation of alkenes produces alcohols in which the hydroxyl group and hydrogen atom are added to adjacent carbon atoms of alkenes in a syn manner.

The regioselectivity is opposite to that of Markovnikov's rule.