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The following compounds can all react as acids. (a) For

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

Solution for problem 50SP Chapter 1

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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1
Problem 50SP

The following compounds can all react as acids.

(a) For each compound, show its conjugate base. Show any resonance forms if applicable.

(b) Rank the conjugate bases in the order you would predict, from most stable to least stable.

(c) Rank the original compounds in order, from strongest acid to weakest acid.

Step-by-Step Solution:

Answer :

(a) For each compound, show its conjugate base. Show any resonance forms if applicable.

Step 1</p>

Conjugate base of CH3COOH:

Acetic acid (CH3COOH) is a weak acid. In water it loses its acidic hydrogen to the water molecule as H+ ion. The acetate ion (CH3COO-) thus formed is the conjugate base of acetic acid.

The resonance structure of acetate ion :

t

Step 2</p>

Conjugate base of CF3COOH :

Trifluoro acetic acid is a strong acid .In water it loses its acidic hydrogen to the water molecule as H+ ion . The acetate ion formed (CF3COO-) thus formed is the conjugate base of trifluoroacetic acid .

The resonance structure of acetate ion :

It does not have resonance structures

Step 3</p>

Conjugate base of peroxyacetic acid :

CH3COOOH is weak acid and its conjugate base is CH3COO-

Step 4 of 5

Chapter 1, Problem 50SP is Solved
Step 5 of 5

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

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 50SP from chapter: 1 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: acid, stable, show, Rank, order. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “The following compounds can all react as acids. (a) For each compound, show its conjugate base. Show any resonance forms if applicable.(b) Rank the conjugate bases in the order you would predict, from most stable to least stable.(c) Rank the original compounds in order, from strongest acid to weakest acid.” is broken down into a number of easy to follow steps, and 50 words. Since the solution to 50SP from 1 chapter was answered, more than 348 students have viewed the full step-by-step answer.

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