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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Chapter 28 Solutions
Organic Chemistry
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