Chapter 19, Problem 19.32P

Rank the compounds in each group in order of increasing boiling point.

a. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{COOH},{\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{O,}{\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{5}}\text{OH}$

b. ${\text{CH}}_{\text{3}}{\text{COCH}}_2\text{CH}{\left({\text{CH}}_{\text{3}}\right)}_2\text{,}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}\text{COOH},{\left({\text{CH}}_{\text{3}}\right)}_2{\text{CHCH}}_2\text{CH}\left(\text{OH}\right){\text{CH}}_3$