Organic Chemistry As a Second Language: Second Semester Topics
Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
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Chapter 10.2, Problem 10.5P
Interpretation Introduction

Interpretation:

Major product has to be predicted for the given reaction.

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.2, Problem 10.5P , additional homework tip  1

Concept Introduction:

Diels-Alder reaction is the 4+2 addition reaction.  Here a total of six pi bonds are involved resulting in formation of one pi bond and two single bonds.  Diels-Alder reaction occurs via a single concerted step and not by involvement of ions.  If a monosubstituted ethylene is used, the product obtained contains a stereocenter.  This can be represented as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.2, Problem 10.5P , additional homework tip  2

If 1,2-disubstituted ethylene is used as starting material, then the configuration of the dienophile is preserved in the product that is formed also.  This means, if the dienophile is in cis-configuration, then the product formed will also have cis-configuration.

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.2, Problem 10.5P , additional homework tip  3

If the dienophile is in trans-configuration, then the product formed will also have trans-configuration.

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.2, Problem 10.5P , additional homework tip  4

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