Chapter 12, Problem 12.11P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism of the given reaction is to be drawn and the major product of the given reaction is to be predicted.

Concept introduction:

In a non-nucleophilic solvent (such as carbon tetrachloride), ${\text{Br}}_{\text{2}}$ or ${\text{Cl}}_{\text{2}}$ adds to an alkene to produce a 1, 2-dihalide. This reaction takes place with anti-addition of the halogens (to yield a vicinal dihalide) through bromonium or chloronium ion intermediate. In water or any other nucleophilic solvent, the treatment of an alkene with molecular halogen produces halohydrin, in which a halogen atom and a $\text{OH}$ group adds in anti-fashion to the alkene carbon atoms. The $\text{OH}$ group ends up on the carbon that can better handle a positive charge (that is greatest substituted carbon atom).