The structures for the products A, B, C, and D showing stoichiometry are to be written. Concept Introduction: For carrying out a nucleophilic substitution on alcohols, first the hydroxyl group of an alcohol gets converted to a good leaving group to a p-toluenesulfonate ester derivative on reaction with p -toluenesulfonyl chloride ( T s C l ) . This reaction proceed with retention of configuration. Then, in the second step, this ester is allowed to react with a nucleophile like O H − . If the mechanism of nucleophilic substitution is S N 2 , then inversion of configuration takes place at the carbon to which alcohol hydroxyl group is attached. Usually, primary alcohols undergo S N 2 mechanism. But whether secondary alcohols undergo S N 2 mechanism or not depends upon the strength of nucleophile.

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Chapter 11, Problem 9PP

Interpretation Introduction

Interpretation:

The structures for the products A, B, C, and D showing stoichiometry are to be written.

Concept Introduction:

For carrying out a nucleophilic substitution on alcohols, first the hydroxyl group of an alcohol gets converted to a good leaving group to a p-toluenesulfonate ester derivative on reaction with p-toluenesulfonyl chloride (TsCl). This reaction proceed with retention of configuration. Then, in the second step, this ester is allowed to react with a nucleophile like OH−.

If the mechanism of nucleophilic substitution is SN2, then inversion of configuration takes place at the carbon to which alcohol hydroxyl group is attached.

Usually, primary alcohols undergo SN2 mechanism. But whether secondary alcohols undergo SN2 mechanism or not depends upon the strength of nucleophile.

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