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The diene lactone shown in part (a) has one

ISBN: 9780321768414 33

Solution for problem 29SP Chapter 15

Organic Chemistry | 8th Edition

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Problem 29SP

The diene lactone shown in part (a) has one electron-donating group $$(-O R)$$ and one electron-withdrawing group $$(C=O)$$. This diene lactone is sufficiently electron-rich to serve as the diene in a Diels-Alder reaction.

(a) What product would you expect to form when this diene reacts with methyl acetylenedicarboxylate, a strong dienophile?

(b) The Diels-Alder product  is not very stable. Upon mild heating, it reacts to produce

$$C O_{2}$$ gas and methyl benzoate $$\left(P h C O O C H_{3}\right)$$, a very stable product. Explain how this strongly exothermic decarboxylation takes place. (Hint: Under the right conditions, the Diels-Alder reaction can be reversible.)

Equation Transcription:

Text Transcription:

(-OR)

(C=O)

COOCH3

CO2

(PhCOOCH3)

Step-by-Step Solution:

Solution 29SP

Step 1

Step 2 of 5

Step 3 of 5

ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: diene, electron, Product, Alder, Diels. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 29SP from 15 chapter was answered, more than 578 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 29SP from chapter: 15 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “?The diene lactone shown in part (a) has one electron-donating group $$(-O R)$$ and one electron-withdrawing group $$(C=O)$$. This diene lactone is sufficiently electron-rich to serve as the diene in a Diels-Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenedicarboxylate, a strong dienophile? (b) The Diels-Alder product is not very stable. Upon mild heating, it reacts to produce $$C O_{2}$$ gas and methyl benzoate $$\left(P h C O O C H_{3}\right)$$, a very stable product. Explain how this strongly exothermic decarboxylation takes place. (Hint: Under the right conditions, the Diels-Alder reaction can be reversible.)Equation Transcription:Text Transcription:(-OR)(C=O)COOCH3CO2(PhCOOCH3)” is broken down into a number of easy to follow steps, and 103 words.

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The diene lactone shown in part (a) has one