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A nitro group effectively stabilizes a negative charge on

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

Solution for problem 9P Chapter 10

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 9P

A nitro group  effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

Step-by-Step Solution:
Step 1 of 3

Here we have to calculate the resonance structures of the appropriate phenoxide ions and have to explain its stability .

Step-1

The stability of a molecule can be explain by its resonance structure and probability of finding delocalization of electrons on the atom.

The resonance structure of phenoxide ion:-

Here the delocalization of -ve charge has been found on the benzene ring at C-2, C-4 and C-6.

Step-2

Resonance structure of nitro group in position 2:-

Nitro group present in the 2nd  position to the carbonyl group , delocalizes -ve charge .

Step-3

Resonance structure of nitro group in position 3:-

The...

Step 2 of 3

Chapter 10, Problem 9P 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: acidic, resonance, Phenol, nitro, atom. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “A nitro group effectively stabilizes a negative charge on an adjacent carbon atom through resonance: Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.” is broken down into a number of easy to follow steps, and 56 words. 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: 9P from chapter: 10 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 9P from 10 chapter was answered, more than 484 students have viewed the full step-by-step answer.

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