Solved: N-Methylpyrrolidine has a boiling point of 81 C, and piperidine has a boiling

Chapter 0, Problem 2-39

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N-Methylpyrrolidine has a boiling point of 81 C, and piperidine has a boiling point of 106 C. (a) Explain this large difference (25 C) in boiling point for these two isomers. (b) Tetrahydropyran has a boiling point of 88 C, and cyclopentanol has a boiling point of 141 C. These two isomers have a boiling point difference of 53 C. Explain why the two oxygen-containing isomers have a much larger boiling point difference than the two amine isomers. (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).