Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 28, Problem 30P
Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

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

Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  1

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

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

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 sigmatropic rearrangement reactions are listed below

SumofthenumberofbondsinthereactingsytemsofbothreagentsReactionconditionsAllowedmodeofbond formationEvennumberThermalAntarafacialPhotochemicalSuprafacialOddnumberThermalSuprafacialPhotochemicalAntarafacial

Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  2Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  3

Carbon migrating with one lobe of its p orbital interacting

Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  4 Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  5

Carbon migrating with both lobe of its p orbital interacting

Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  6Organic Chemistry, Chapter 28, Problem 30P , additional homework tip  7

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

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