Chapter 3, Problem 32P

Arrange the following compounds in order of decreasing acidity:

(a) ${\text{CH}}_{\text{3}}{\text{CH=CH}}_{\text{2}}{\text{,CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}{\text{, CH}}_{\text{3}}\text{C}\equiv \text{CH}$

(c) ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{OH,CH}}_{\text{3}}{\text{CH}}_{\text{2}}\stackrel{+}{\text{O}}{\text{H}}_{\text{2}}{\text{, CH}}_{\text{3}}{\text{OCH}}_3$

(b) ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH,CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{H, CH}}_{\text{3}}{\text{CHClCO}}_{\text{2}}\text{H}$