Aspirin (acetylsalicylic acid) is produced by the acetylation of salicylic acid ($o$-hydroxybenzoic acid) with acetic anhydride in the presence of an acid catalyst:

Salicylic acid is $o$-hydroxybenzoic acid.

When phenol is treated with chloroform ($\text{CHCl}_3$) in the presence of aqueous sodium hydroxide, an aldehyde group ($-\text{CHO}$) is introduced at the ortho position of the benzene ring, yielding salicylaldehyde ($o$-hydroxybenzaldehyde). This reaction proceeds via the intermediate dichlorocarbene ($:\text{CCl}_2$) electrophile and is universally known as the Reimer-Tiemann reaction.

To find the IUPAC name for $\text{C}_6\text{H}_5-\text{C}(\text{CH}_3)_2-\text{OH}$:

• Longest carbon chain containing the principal functional group (alcohol $-\text{OH}$): A 3-carbon chain (propane), numbered $\text{C}^1\text{H}_3-\text{C}^2(\text{OH})(\text{C}_6\text{H}_5)-\text{C}^3\text{H}_3$.
• The principal functional group $-\text{OH}$ is at carbon 2 $\rightarrow$ propan-2-ol.
• Carbon 2 has a phenyl group ($\text{C}_6\text{H}_5-$) substituent.

Analysis of intermolecular forces and boiling points of comparable molecular weights:

• $n$-Butane (B): Non-polar hydrocarbon with only weak London dispersion forces $\rightarrow$ lowest boiling point ($309\text{ K}$ or below, $\text{b.p.} = -0.5^\circ\text{C} \approx 272.5\text{ K}$).
• Ethoxyethane (D): Weak dipole-dipole interactions without hydrogen bonding $\rightarrow \text{b.p.} = 307.6\text{ K}$.
• Pentan-1-al (C): Polar carbonyl group with strong dipole-dipole attractions $\rightarrow \text{b.p.} = 376\text{ K}$.
• Pentan-1-ol (A): Extensive intermolecular hydrogen bonding between hydroxyl groups $\rightarrow$ highest boiling point ($411\text{ K}$).