Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 30.SE, Problem 33AP
Interpretation Introduction

Interpretation:

The stereochemistry, suprafacial or antarafacial, expected for the photochemical [1,5] sigmatropic rearrangement reaction is to be stated.

Concept introduction:

Sigmatropic rearrangements involve the migration of a σ bond present at the end or in the middle of the system across the π electron system from one position to another. They are represented by [m,n] where m and n represents the number of atoms between the bond being broken and the bond being formed in two directions.

If even number of electron pair is involved then thermal reaction occur through antarafacial pathway and photochemical reactions occur through suprafacial pathway.

If odd number of electron pair is involved then thermal reaction occur through suprafacial pathway and photochemical reactions occur through antarafacial pathway.

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a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?
Which of the following describes the sigmatropic rearrangement that occurs in the reaction shown below? CH2 CH3 dede CH3 CH₂ [3,3] sigmatropic rearrangement [2,3] sigmatropic rearrangement [1,4] sigmatropic rearrangement [1,3] sigmatropic rearrangement [1,5] sigmatropic rearrangement
Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the σ bonds that are broken or formed in each reaction
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