Concept:
Boiling points of alcohols depend on:
- Hydrogen bonding (present in all alcohols)
- Molecular mass (higher mass $\Rightarrow$ higher boiling point)
- Branching (more branching $\Rightarrow$ lower boiling point due to less surface area)
Step 1: Compare carbon chain length.
Higher carbon chain $\Rightarrow$ stronger van der Waals forces $\Rightarrow$ higher boiling point.
So:
\[
\text{propan-1-ol}<\text{butanol isomers}<\text{pentan-1-ol}
\]
Step 2: Compare branching among butanol isomers.
Butan-1-ol = primary alcohol (less branched)
Butan-2-ol = secondary alcohol (more branched)
More branching $\Rightarrow$ lower boiling point.
So:
\[
\text{butan-2-ol}<\text{butan-1-ol}
\]
Step 3: Combine both trends.
\[
\text{Propan-1-ol}<\text{butan-2-ol}<\text{butan-1-ol}<\text{pentan-1-ol}
\]