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Predict the major product for each proposed Diels–Alder

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 16P Chapter 15

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 16P

Problem 16P

Predict the major product for each proposed Diels–Alder reaction. Include stereochemistry where appropriate.

Step-by-Step Solution:
Step 1 of 3

Solution 16P

Diels-Alder reaction: The cyclo addition reaction of diene with a dienophile yields a cyclo hexene.

Example: 1,3 butadiene undergoes cyclo addition reaction with ethylene (diene) to form a cyclohexene. This reaction takes place through a six membered cyclic transition state.

The reaction as follows:

(a) cyclopenta-1,3-diene reacts with acrylonitrile (dienophile) to form a endo product as a major product.

The reaction is as follows:

(b) 3-methoxypenta-1,3-diene reacts with benzoquinone (dienophile) to form a endo product as a major product.

The reaction is as follows:

(c) 1,4-dipheylbuta-1,3-diene reacts with furan-2,5-dione (dienophile) to form a endo product as a major product.

The reaction is as follows

Step 2 of 3

Chapter 15, Problem 16P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Predict the major product for each proposed Diels–Alder