Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis 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.”

Organic Chemistry (8th Edition), 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

Organic Chemistry (8th Edition), Chapter 28, Problem 32P , additional homework tip  2Organic Chemistry (8th Edition), Chapter 28, Problem 32P , additional homework tip  3

Carbon migrating with one lobe of its p orbital interacting

Organic Chemistry (8th Edition), Chapter 28, Problem 32P , additional homework tip  4 Organic Chemistry (8th Edition), Chapter 28, Problem 32P , additional homework tip  5

Carbon migrating with both lobe of its p orbital interacting

Organic Chemistry (8th Edition), Chapter 28, Problem 32P , additional homework tip  6Organic Chemistry (8th Edition), 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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