16. Conjugated Systems
Diels-Alder Forming Bridged Products
2:21 minutes
Problem 15-29b
Textbook Question
Textbook QuestionThe diene lactone shown in part (a) has one electron-donating group (-OR) and one electron-withdrawing group (C=O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.
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(b) The Diels–Alder product A is not very stable. Upon mild heating, it reacts to produce CO2 gas and methyl benzoate (PhCOOCH3), a very stable product. Explain how this strongly exothermic decarboxylation takes place. (Hint: Under the right conditions, the Diels–Alder reaction can be reversible.)
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