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(a) Explain how pyrrole is isoelectronic with the

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

Solution for problem 16P Chapter 16

Organic Chemistry | 8th Edition

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

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Problem 16P

Problem 16P

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.

(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?

(c) Draw resonance forms to show the charge distribution on the pyrrole structure.

Step-by-Step Solution:
Step 1 of 3

Solution 16P

(a) The pyrrole is an aromatic five-membered heterocyclic, with one nitrogen atom and two double bonds. Although it may seem that pyrrole has only four pi electrons, the nitrogen atom has alone pair of electrons.

The cyclopentadienyl anion is an aromatic five-membered ring, with two double bonds and negative charged of lone pair of electrons. So, it is also contain 6 pi electron. So, it is isoelectronic with cyclopentadienyl anion.

(b) These two compounds are aromatic compounds. The cyclopentadiene is unusually acidic because loss of a proton converts the non-aromatic diene to the aromatic cyclopentadienyl anion. The pyrrole has amino group. So, it has a basic nature. The pyrrole has 4 pi electrons and the nitrogen atom has a lone pair of electrons. So, it has 6

Pi electrons. The cyclopentadienyl anion has 4 pi electrons and the negatively charged of lone pair of electrons of methylene group. So, i is also 6 pi electrons

The cyclopentadienyl anion does not have any heteroatom but pyrrole has nitrogen atom (hetero atom)

(c) The lone pair of electrons on the nitrogen atom undergoes resonance to form four resonance contributors. They are shown below.

Step 2 of 3

Chapter 16, Problem 16P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This full solution covers the following key subjects: cyclopentadienyl, pyrrole, anion, isoelectronic, distribution. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 16P from 16 chapter was answered, more than 1027 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 16P from chapter: 16 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. The answer to “(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.” is broken down into a number of easy to follow steps, and 33 words.

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