2. Molecular Representations

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.

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(a) CH₃CH₂OCH₃ or CH₃CH(OH)CH₃

(b) CH₃CH₂CH₂CH₃ or CH₃CH₂CH₂CH₂CH₃

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

b. isopropyl chloride and tert-butyl bromide

PRACTICE:Which of the following pairs of molecules would have the highest boiling point?

Rank the following compounds from highest boiling to lowest boiling:

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

c. 2,2,5-trimethylhexane or nonane

Explain why

a. H₂O (100 °C) has a higher boiling point than CH₃OH 165 °C2.

b. H₂O (100 °C) has a higher boiling point than NH₃ (-33 °C).

Rank the boiling points of the following molecules. Explain your ranking ( 1 = highest bp; 3 = lowest bp ).

Explain the following:

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

Choose the molecule in each pair you'd expect to have the higher boiling point. Explain your reasoning.

(b)

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

e. CH₃(CH₂)₃CH₃

f. CH₂=CH—CH₂CH₃

g. CH₃COCH₃

h. CH₃CH₂COOH

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

b. nonane or 2-methylheptane

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(d)