Rank the following compounds from highest boiling to lowest boiling:

Draw the hydrogen bonding that takes place between

c. a molecule of dimethyl ether and two molecules of water.

d. two molecules of trimethylamine and a molecule of water.

Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.

N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.

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.

List each set of compounds in order of increasing boiling point.

a. hexane, octane, and decane

Explain the following:

a. 1-Hexanol has a higher boiling point than 3-hexanol.

Explain why

c. H₂O (100 °C) has a higher boiling point than HF 120 °C2.

d. HF 120 °C2 has a higher boiling point than NH₃ (-33 °C).

Which of the following compounds forms hydrogen bonds between its molecules?

1. CH₃CH₂OCH₂CH₂OH

2. CH₃CH₂N(CH₃)₂

3. CH₃CH₂CH₂CH₂Br

In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.

c. 2,2,5-trimethylhexane or nonane