Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12, Problem 41P
Interpretation Introduction

(a)

Interpretation: The product formed when A is treated with mCPBA is to be predicted.

Concept introduction: In the presence of peroxide, alkene is oxidized to epoxide. This is known as epoxidation. This is a syn addition. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. mCPBA is meta-chloroperoxybenzoicacid.

Interpretation Introduction

(b)

Interpretation: The product formed when A is treated with Br2,H2O followed by base is to be predicted.

Concept introduction: The reaction between bromine and alkene proceeds via the formation of cyclic bromonium intermediate. The reaction of bromine in water is an anti addition on alkene. This is a regioselective reaction, the hydroxyl group adds to the more substituted carbon of the double bond.

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Chapter 12 Solutions

Organic Chemistry (6th Edition)

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