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Part of a synthesis by E. J. Corey and David Watt (Harvard

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

Solution for problem 38SP 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 38SP

Part of a synthesis by E. J. Corey and David Watt (Harvard University) involves the Diels–Alder cycloaddition of the following pyrone and cyclohexenone. The initial reaction gives the endo product, which loses carbondioxide in a retro-Diels–Alder to generate a diene with predictable stereochemistry and functionality. IR and UV spectroscopy of the final product show that it contains a diene conjugated with an ester, and an unconjugated ketone. Determine the structures of the intermediate and the final product, with particular attention to their stereochemistry.

Step-by-Step Solution:
Step 2 of 3

Solution 38SP

Diels-Alder reaction is a concerted reaction between a diene and a dienophile. It usually results in the formation of new six-membered ring.

Example: 1,3-butadiene undergoes cycloaddition reaction with ethylene (diene) to form a cyclohexene. This reaction takes place through a six membered cyclic transition state. The reaction as follows:

Treatment of methyl 2-oxo-2H-pyran-3-carboxylate with 4-methylcyclohex-3-enone gives the following Diels-alder product.

Step 3 of 3

Chapter 15, Problem 38SP is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

Since the solution to 38SP from 15 chapter was answered, more than 353 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 38SP from chapter: 15 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “Part of a synthesis by E. J. Corey and David Watt (Harvard University) involves the Diels–Alder cycloaddition of the following pyrone and cyclohexenone. The initial reaction gives the endo product, which loses carbondioxide in a retro-Diels–Alder to generate a diene with predictable stereochemistry and functionality. IR and UV spectroscopy of the final product show that it contains a diene conjugated with an ester, and an unconjugated ketone. Determine the structures of the intermediate and the final product, with particular attention to their stereochemistry.” is broken down into a number of easy to follow steps, and 83 words. This full solution covers the following key subjects: stereochemistry, Product, final, Alder, diene. This expansive textbook survival guide covers 25 chapters, and 1336 solutions.

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Part of a synthesis by E. J. Corey and David Watt (Harvard

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