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 S N 1 mechanism. The S N 1 reaction is nucleophilic substitution reaction in which nucleophile is replaced by a leaving group. S N 1 indicates unimolecular, substitution and nucleophilic reaction. S N 1 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.

Question

Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?

Answer 1

Question

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 S_N1 mechanism. The S_N1 reaction is nucleophilic substitution reaction in which nucleophile is replaced by a leaving group. S_N1 indicates unimolecular, substitution and nucleophilic reaction.

S_N1 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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