Predict which member of each pair is more acidic, and

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