Question

Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order. Enter your answer in the answer box below. a. 4-nitrophenol b. cyclohexanol c. 2,6-difluorocyclohexanol d. 4-bromophenol

Answer 1

Answer:

(a) > (d) > (c) > (b)

Explanation:

Acidic character is based upon inductive effect of the functional group that are attached to parent chain.

1. Nitro is a -I group which makes phenol acidic due to increased resonance,  2. bromine is a -I group but it is weaker than nitro group

3. phenol is more acidic than cyclohexanol due to resonance stabilization of resonance and among halogen F>Cl>Br>I is the order of acidity

4. cyclohexanol will be weakest as  it is not associated with any -I groups here.

so the order of acidity will be

(a). 4-nitropheno >  (d). 4-bromophenol > (c). 2,6-difluorocyclohexanol  >               (b). cyclohexanol