Organic Chemistry: Principles And Mechanisms (second Edition)
Organic Chemistry: Principles And Mechanisms (second Edition)
2nd Edition
ISBN: 9780393630749
Author: KARTY, Joel
Publisher: W. W. Norton & Company
Question
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Chapter 11, Problem 11.7P
Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Chapter 11 Solutions

Organic Chemistry: Principles And Mechanisms (second Edition)

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