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The highly reactive triple bond of benzyne is a powerful

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

Solution for problem 25P Chapter 17

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 25P

Problem 25P

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Step-by-Step Solution:

Solution:

Here we have to predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Step 1

Diels-Alder reaction:-

The Diels–Alder reaction is a cycloaddition reaction (specifically, a [4+2] cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system.

In this reaction cyclopentadiene (conjugated diene) is added with the dienophile (substituted alkene produced from chlorobenzene) in presence of NaOH on heating gives the following adduct.

(Conjugated diene)(dienophile)            (Adduct)

Step 2 of 1

Chapter 17, Problem 25P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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The highly reactive triple bond of benzyne is a powerful