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Solved: The following compounds can all react as acids.

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

Solution for problem 52SP 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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Problem 52SP

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:

Solution 52SP :

Step 1:

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

A resonance form is another way of drawing a Lewis dot structure for a compound when there is more than one possibility of placing valence or lone pairs of electrons, but the atoms in the resonance forms should have identical position. Equivalent Lewis structures of same compound are called resonance forms. To find the conjugate base of an acid, we remove one hydrogen atom and decrease the charge of the compound by 1.

Step 2:

(i)

                

The compound is CH3COOH (Acetic acid).  The conjugate base of CH3COOH is CH3COO -. The structure of conjugate base and the resonance forms of the compound is shown below :

(ii)

The compound is CH3CONH2(Acetamide). The conjugate base of CH3CONH2 is CH3CONH -. The structure of conjugate base and the resonance forms of the compound is shown below :

(iii)

The compound is CH3SO2H(Methanesulfinic acid). The conjugate base of CH3SO2H is CH3SO2-. The structure of conjugate base and the resonance forms of the compound is shown below :

(iv)

The above compound is CH3SO3H (Methanesulfonic acid). The conjugate base of CH3SO3H is CH3SO3 -. The structure of conjugate base and the resonance forms of the compound is shown below :

(v)

The above compound is FSO3H(Fluorosulfuric acid). The conjugate base of FSO3H is FSO3 -. The structure of conjugate base and the resonance forms of the compound is shown below :

Step 3 of 4

Chapter 1, Problem 52SP is Solved
Step 4 of 4

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: 52SP from chapter: 1 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. 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. This full solution covers the following key subjects: acid, stable, show, Rank, order. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Since the solution to 52SP from 1 chapter was answered, more than 1218 students have viewed the full step-by-step answer.

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