Discussion
Which of the following amine has the highest boiling point?
Answer: B
The highest boiling point belongs to CH3CH2CH2CH2NH2 (n-butylamine).
Two factors decide the order: molar mass, and hydrogen bonding through N-H bonds. Primary amines have two N-H hydrogens, secondary amines one and tertiary amines none, so for amines of the same molar mass the order is primary > secondary > tertiary.
n-Butylamine, diethylamine and ethyldimethylamine are isomers (C4H11N): n-butylamine boils at about 78 °C, diethylamine at about 56 °C, and the tertiary amine at about 37 °C, since it cannot hydrogen bond with itself. Ethylamine and n-propylamine are primary but lighter, so they boil lower.
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