ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT
ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT
2nd Edition
ISBN: 9781119288510
Author: Klein
Publisher: WILEY
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Chapter 14.10, Problem 4LTS
Interpretation Introduction

Interpretation: The product along with its mechanism has to be predicted.

Concept Introduction:

Ring opening reactions occur when an Epoxide is attacked by strong nucleophile. The mechanism of transformation generally occurs in two steps as nucleophilic attack and proton transfer.

ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT, Chapter 14.10, Problem 4LTS , additional homework tip  1

In first step, hydroxide acts as nucleophile and helps in opening of ring by SN2 process.

ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT, Chapter 14.10, Problem 4LTS , additional homework tip  2

In second step, the alkoxide ion is protonated by Water.

ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT, Chapter 14.10, Problem 4LTS , additional homework tip  3

These kinds of reactions involve in two significant features called as regiochemistry and stereochemistry.

  1. 1) Regiochemistry: The nucleophilic attack is seen at the less substituted(less hindered) position in an unsymmetrical epoxide. The less hindered position (steric effect) is expected from SN2 process.
  2. 2) Stereochemistry: Inversion of configuration is observed when nucleophilic attack is seen at chirality center. This steric effect is also expected from SN2 process.

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Chapter 14 Solutions

ORGANIC CHEMISTRY GGC>CUSTOM<-TEXT

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