Chapter 8.4, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product expected from oxymercuration-demercuration of 1-pentene is to be given.

Concept introduction:

In the oxymercuration-demercuration process, in the first step, the electrophilic addition of Hg²⁺ to the double bond in alkene takes place to give a mercurinium ion. In the next step the mercurinium ion reacts with water to yield an organomercury product. In the last step, NaBH₄ removes mercury from the organomercury product to give a more highly substituted alcohol, corresponding to Markovnikov regiochemistry, as the product.

To give:

The product expected from oxymercuration-demercuration of 1-pentene.

Interpretation Introduction

b)

Interpretation:

The product expected from oxymercuration-demercuration of 2-methyl-2-pentene is to be given.

Concept introduction:

In the oxymercuration-demercuration process, in the first step, the electrophilic addition of Hg²⁺ to the alkene takes place to give a mercurinium ion. In the next step, the mercurinium ion reacts with water to yield an organomercury product. In the last step, reaction with NaBH₄ removes mercury from the organomercury product to give a more highly substituted alcohol, corresponding to Markovnikov regiochemistry, as the product.

To give:

The product expected from oxymercuration-demercuration of 2-methyl-2-pentene.