Chapter 10, Problem 10.58P

Interpretation Introduction

Interpretation:

Synthetic intermediates A and B has to be drawn.

Concept Introduction:

Conversion of alcohol into haloalkane:

Conversion of primary and secondary alcohols to Chloroalkane is thionyl chloride. The reaction is carried out in the presence of base such as pyridine or trimethylamine.

The reaction of an alcohol with thionyl chloride is the formation of an alkyl Chlorosulfite that converts hydroxide ion (poor leaving group) into Chlorosulfite (good leaving group).  Nucleophilic displacement of this leaving group gives product.

Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.