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The diene lactone shown in part (a) has one
Chapter 9, Problem 29SP(choose chapter or problem)
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)
Questions & Answers
QUESTION:
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)
ANSWER:
Solution 29SP
Step 1
