Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
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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In the box on the right, draw the best resonance structure of the compound on the left. Draw electron-flow arrows on the structure on the left to indicate how the electrons reorganize to give the structure on the right. Interactive 3D display mode CH₁₂ Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. H± EXP. CONT を口か H3C. CH3 H C Zo S CI Br P9 F

Chapter 11 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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