Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 28, Problem 32P
Interpretation Introduction

Interpretation:

The product of the reaction for given two reactants should be drawn.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  1

Sigma tropic rearrangement reactions are designated with digits. For example a [1, 3] sigma tropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigma tropic rearrangement reactions are listed below

SumofthenumberofbondsinthereactingsytemsofbothreagentsReactionconditionsAllowedmodeofbond formationEvennumberThermalAntarafacialPhotochemicalSuprafacialOddnumberThermalSuprafacialPhotochemicalAntarafacial

Migration of carbon and hydrogen will occur in a sigmatropic rearrangement reaction. Migration of hydrogen in suprafacial and antarafacial rearrangement can be represented as follows,

Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  2Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  3

Carbon migrating with one lobe of its p orbital interacting

Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  4 Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  5

Carbon migrating with both lobe of its p orbital interacting

Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  6Organic Chemistry, Chapter 28, Problem 32P , additional homework tip  7

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