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 10.3, Problem 10.11P
Interpretation Introduction

Interpretation:

Major product has to be predicted for the given reaction.

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.3, Problem 10.11P , 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 10.3, Problem 10.11P , additional homework tip  2

If a cyclic diene is considered, then the product obtained will be a bicyclic compound.  Diels-Alder reaction that involves cyclopentadiene results in a bicyclic structure.  If the dienophile has a cis configuration, then the two groups have to be in cis configuration to each other.  The product obtained will have the groups in endo position.  It is a meso compound.

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.3, Problem 10.11P , additional homework tip  3

If the dienophile has a trans configuration, then the two groups have to be in trans configuration to each other.  The product obtained will have the groups as shown below,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 10.3, Problem 10.11P , additional homework tip  4

The above two structures are enantiomers.

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