Chapter 2, Problem 2.23P

Rank the compounds in each group in order of increasing acidity.

a. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH}$, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$

b. ${\text{BrCH}}_{\text{2}}\text{COOH}$, ${\text{CH}}_3{\text{CH}}_{\text{2}}\text{COOH}$, ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$

c. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$, ${\left({\text{CH}}_{\text{3}}\right)}_3\text{N}$, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH}$