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Recall (Section 16-10) that two positions of anthracene

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

Solution for problem 39SP Chapter 16

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 39SP

Recall (Section 16-10) that two positions of anthracene sometimes react more like polyenes than

like aromatic compounds.

(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends of adiene, appropriate for a Diels–Alder reaction.

(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic lab experiment. Predict the product of this Diels–Alder reaction.

Step-by-Step Solution:
Step 1 of 3

Solution 39SP

(a)

The resonance energy of anthracene is 84k. cal/mol which is less than the resonance energy for three separate benzene rings so anthracene is not as strongly stabilized as benzene.

Anthracene undergo, 1,4 - addition at the 9-and 10-positions to give a product with two isolated, fully aromatic benzene rings. So anthracene behave like a diene and can undergo...

Step 2 of 3

Chapter 16, Problem 39SP is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Recall (Section 16-10) that two positions of anthracene

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