The compounds are not optically active, the reason has to be predicted. Concept Introduction: Diels-Alder reaction: A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product. Conformation of Diene: S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer. S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer. Condition for Diels-Alder reaction: The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

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Chapter 8.19, Problem 55P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

b)

Interpretation Introduction

Interpretation: The order of diene reactivity has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

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