Question

Arrange the compounds in each set in the order of increasing boiling point. (a) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{COOH}\) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CHO}\) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CH}_{2} \mathrm{OH}\) (b) CCC(=O)O CCCCO CCOCC

Short answer

Question: Arrange the following compounds in order of increasing boiling points: a) Heptanal, 1-heptanol, and hexanoic acid b) Ether, 1-butanol, and propanoic acid Answer: a) Heptanal < 1-heptanol < Hexanoic acid b) Ether < 1-butanol < Propanoic acid

Step-by-step solution

Set (a) - Analyzing Intermolecular Forces

1. Hexanoic acid has a carboxylic acid group, which can form hydrogen bonds due to its -OH group. 2. Heptanal has an aldehyde group, which has dipole-dipole interactions because of the polarized C=O bond. 3. 1-heptanol has an alcohol group, which can form hydrogen bonds due to its -OH group.

Set (a) - Comparing Boiling Points

All three compounds have relatively equal sizes and similar van der Waals forces. However, both hexanoic acid and 1-heptanol can form hydrogen bonds, which are stronger than heptanal's dipole-dipole interactions. Therefore, the order of increasing boiling points for set (a) is: Heptanal < 1-heptanol < Hexanoic acid

Set (b) - Analyzing Intermolecular Forces

1. Propanoic acid has a carboxylic acid group, which can form hydrogen bonds due to its -OH group. 2. 1-butanol has an alcohol group, which can form hydrogen bonds due to its -OH group. 3. Ether has an ether group, which has dipole-dipole interactions because of the polarized C-O bond.

Set (b) - Comparing Boiling Points

Ether has weaker dipole-dipole interactions compared to the hydrogen bonding in propanoic acid and 1-butanol. Between propanoic acid and 1-butanol, propanoic acid has a more polarized functional group (C=O) that contributes to stronger hydrogen bonding. Therefore, the order of increasing boiling points for set (b) is: Ether < 1-butanol < Propanoic acid