Chapter 7, Problem 52P

Interpretation Introduction

Interpretation:

The structures of carbocation intermediatesformed is to be determinedand the ions formedby methyl shift and the pathway that will predominates are to be predicted.

Concept introduction:

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The dehydration of secondary and tertiary alcohol proceeds through $\text{E1}$ mechanism.

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The $\text{E1}$ mechanism involves the formation of carbocation.

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Thestability order of carbocation is methyl $<$ primary $<$ secondary $<$ tertiary.

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The carbocation can be stabilized by rearrangement due to the shift of hydride or methyl group of adjacent carbons.

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The selection of hydride or methyl group shift depends on the stability of the carbocation formed.