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Pyrrole undergoes electrophilic aromatic substitution more

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

Solution for problem 49SP Chapter 19

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 49SP

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

(a) Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion,  .Be careful to draw all the resonance structures of the intermediate.

(b) Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than the 3-position.

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Solution 49SP

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Chapter 19, Problem 49SP is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Pyrrole undergoes electrophilic aromatic substitution more

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