2. Molecular Representations
Intermolecular Forces
2:57 minutes
Problem 2.34c
Textbook Question
Textbook QuestionN-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.
c. N,N -Dimethylformamide has a boiling point of 150 °C, and N-methylacetamide has a boiling point of 206 °C, for a difference of 56 °C. Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers.
Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).
<IMAGE> N-methylpyrrolidine, bp 81°C
<IMAGE> tetrahydropyran, bp 88°C
<IMAGE> N,N-dimethylformamide, bp 150°C
<IMAGE> piperidine, bp 106°C
<IMAGE> cyclopentanol, bp 141°C
<IMAGE> N-methylacetamide, bp 206°C
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