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Predict which member of each pair is more acidic, and

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

Solution for problem 35SP 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 35SP

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

(a) cyclopentanol or 3-chlorophenol

(b) cyclohexanol or cyclohexanethiol

(c) cyclohexanol or cyclohexanecarboxylic acid

(d) butan-1-ol or 2,2-dichlorobutan-1-ol

Step-by-Step Solution:

Solution 35SP:

Here, we are going to predict the member of each pair which have more acidity with reason.

The acidity of an alcohol depends on the stability of its conjugate base. The acidity of an alcohol depends on the following factors.

(1)electronegativity,

(2)Inductive and resonance effects,

(3) Polarizability, and  solvation

(a) cyclopentanol or 3-chlorophenol

Step 1: The structure of the compounds are as follows

Here, 3-chlorophenol is more acidic than cyclopentanol. This is because, the conjugate base of 3-chlorophenol is stabilized by resonance structure of phenoxide ion. Whereas, in in the conjugate base of cyclopentanol has no resonance form.

(b) cyclohexanol or cyclohexanethiol

Step 2: The structures of the compounds are as follows

Here,  cyclohexanethiol has more acidic than cyclohexanol. This is because, down the group of the periodic table, acidity increases with size. Thus, the negative charge on the larger anion is distributed over a large volume which results greater stability.

(c) cyclohexanol or cyclohexanecarboxylic acid

Step 3 of 4

Chapter 10, Problem 35SP is Solved
Step 4 of 4

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

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