Step 1: Dimerization via hydrogen bonding.
Carboxylic acids like propanoic acid associate into dimers through two intermolecular hydrogen bonds.
Step 2: Behavior in vapor phase.
In vapor, without competing solvent interactions, propanoic acid readily forms dimers.
Step 3: Behavior in aqueous solution.
Water molecules compete for hydrogen bonds, disrupting acid–acid association; dimers do not persist.
Step 4: Behavior in aprotic solvents.
Aprotic solvents lack strong hydrogen-bond-donating ability, allowing the dimer to remain intact.
Step 5: Conclusion.
Propanoic acid exists as a dimer in vapor phase and in aprotic solvents.