Question

Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order. a. 2,4-dinitrophenol b. phenol c. 2,4-difluorocyclohexanol d. cyclohexanol

Answer 1

Compounds in order of increasing acidity will be written as d<c<b<a.

What is acidity?

The quantity of hydroxyl ions that a basic molecule may create in an aqueous solution is what is known as the acidity of bases. The quantity of hydronium ions that a substance may create in an aqueous solution determines how basic an acid is.

a, b are more acidic than c and d because of OH group attached to sp2 hybridised carbon which provide resonance stability for conjugate base

in c f has -I effect which increases acidity in a, NO2 has -m effect which increases acidity so increasing order is d<c<b<a

that is  cyclohexanol <  2,4-difluorocyclohexanol <  phenol < 2,4-dinitrophenol

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