Question

For the following Diels-Alder reaction,the product skeletal structure and configuration at the bridgehead carbons are given...

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For the following Diels-Alder reaction,the product skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters, which are the only ones shown in letter form C.

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Answer #1
Concepts and reason

Diels-Alder reaction is a cycloaddition reaction in which two molecules combines to form a ring. In this reaction π bond converted into sigma bond. Stereochemistry is maintained in the reaction because reaction is concerted. It is stereospecific reaction.

Fundamentals

A compound with conjugated double bond is called as diene.

Diene

A substituted alkene or alkyne is represented as dienophile.

H
Н.
н
Н
Dienophiles
I
I

Example:

+
Dienophile
Diene
Product
Transition

The transition intermediate formed during the reaction of cyclohexa-diene with maleic anhydride was given below

O
Endo-transition
+
(major)
Dienophile
Diene
Exo-transition
(minor)

Нн
Endo-product
(major)
Endo-transition
(major)
Нн
Endo-product
(minor)
Exo-transition
(minor)
I,

Ans:

Product of the reaction is

но
C
нн
Endo-product
(major)

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Answer #2

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source: Homework
answered by: Hazael Chub
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