Rank the following isomers from the one with the lowest boiling point to the one with the highest boiling point. Explain your answer.

Using the intermolecular forces of attraction concept, explain why propionic acid (bp = 141 °C) has a higher boiling point than propaneperoxoic acid (bp = 120°C; explodes) even though the former has a lower molecular weight than the latter.

The two N-containing isomers below have a boiling point difference of 19.0 °C. Meanwhile, the two O-containing isomers have a boiling point difference of 83.2 °C. The two N-containing isomers have a much smaller boiling point difference than the two O-containing isomers. Explain this observation.

Identify: (i) compounds that can form intermolecular hydrogen bonds; (ii) compounds that can form hydrogen bonds with water; (iii) compounds which you think are soluble in water. CH₃(CH₂)₂CH₃, CH₂=CH-CH₃, CH₃CHO and CH₃COOH.

Determine which compound has the higher boiling point for each of the following pairs: (i): 3-methylpiperidine or 1,3-dimethylpyrrolidine, and (ii): 2,4-dimethylpyrrolidine or 4-methylpyrrolidin-2-one. Explain.

Choose the molecules that would form a hydrogen bond to methanol.

i. CH₃CH₂CH₂OCH₂CH₂CH₂OH

ii. CH₃CH₂CH₂N(CH₃)₂

iii. CH₃CH₂CH₂Cl

Determine the smallest possible straight-chain alkane that is liquid at 37 °C.