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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 carbon dioxide in a retroDiels-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.

Equation Transcription:

Text Transcription:

CO_2Me

H_3C

150°C

-CO_2

Step-by-Step Solution:
Step 1 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

Decarboxylation of the Diels-alder product gives the following diene in the product.

Step 2 of 3

Chapter 15, Problem 38SP is Solved
Step 3 of 3

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

Since the solution to 38SP from 15 chapter was answered, more than 522 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 carbon dioxide in a retroDiels-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. Equation Transcription:Text Transcription:CO_2MeH_3C150°C-CO_2” is broken down into a number of easy to follow steps, and 87 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