Chapter 8.SE, Problem 40MP

Interpretation Introduction

Interpretation:

Given that treatment of 4-pentene-1-ol with aqueous bromine yields 2-(bromomethyl) tetrahydrofuran rather than expected bromohydrin. A mechanism for this reaction, using curved arrows to show the electron movement, is to be proposed.

Concept introduction:

The addition of bromine to alkenes follows anti stereochemistry. In the first step a cyclic bromonium ion is formed, with the elimination of a bromide ion, by the attack of the π electrons of the double bond on bromine. In the second step a nucleophile attacks the bromonium ion from the less shielded opposite side to give an anti product.

To propose:

A mechanism for the reaction in which 4-pentene-1-ol on treatment with aqueous bromine yields 2-(bromomethyl)tetrahydrofuran using curved arrows to show the electron movement.