Chapter 12, Problem 61P

Branching in an alkane chain decreases surface area. As a result, a branched-chain alkane tends to have a lower boiling point than a straight-chain alkane with the same number of carbons. Keeping this in mind, rank the alkane isomers in each group in order of increasing boiling point.

 a. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}},{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{3}},{\left({\text{CH}}_{\text{3}}\right)}_{\text{4}}\text{C}$

 b. ${\left(\text{CH3}\right)}_{\text{2}}\text{CHCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}},{\text{ CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{4}}{\text{CH}}_{\text{3}},{\text{ CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{CH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}$