Question

Rank with respect to boiling point. What am I doing wrong?

CH3CH2CH2OH > (CH3)2CH(C=0)H > CH3CH2CO2H > HO2C(CH2)2CO2H > (CH3CH2)2NH > (CH3)2CHCH2CH3 > CH4

Answer 1

HO2C-C(CH2)-CO2H>CH3CH2CO2H>CH3CH2CH2OH>(CH3CH2)2NH>(CH3)2CH(C=O)H>branched chain> methane.

Boiling points are based on polarity and weight. More polar and more heavy, the higher the boiling point. Hydrogen bonds are favored whenever possible. That way, acids almost always take preference. Hope that helps