EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 28, Problem 32P
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.”

EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , 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

EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  2EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  3

Carbon migrating with one lobe of its p orbital interacting

EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  4 EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  5

Carbon migrating with both lobe of its p orbital interacting

EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  6EBK ORGANIC CHEMISTRY, Chapter 28, Problem 32P , additional homework tip  7

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

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