Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 28.7, Problem 11P
Interpretation Introduction

Interpretation:

Determine the mechanism for cleavage reaction of the p-Dimethoxytrityl (DMT) ether.

Concept introduction:

The cleavage reaction of p-Dimethoxytrityl (DMT) takes place by the SN1 mechanism. The SN1 reaction is nucleophilic substitution reaction in which nucleophile is replaced by a leaving group. SN1 indicates unimolecular, substitution and nucleophilic reaction.

SN1 reaction takes place in following two steps:

  • Leaving group leaves and leaves behind carbocation intermediate.
  • Nucleophilic attack on the carbocation to form final product.

The stability of carbocation i.e. 3°>2°>1°, determines the rate of the reaction.

Given information:

The information given in the question is that the DMT ether is easily cleaved by the treatment with mild acid.

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