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Which of the following compounds exhibits intermolecular hydrogen bonding?

1. Ortho-chlorophenol
2. Chloral
3. Meta-hydroxybenzaldehyde
4. Para-hydroxybenzaldehyde

Correct answer: Para-hydroxybenzaldehyde

Solution

Ortho-chlorophenol forms an intramolecular hydrogen bond between the OH proton and the Cl atom (ring geometry allows proximity), suppressing intermolecular H-bonding. Chloral (CCl3CHO) has no OH donor. Meta- and para-hydroxybenzaldehyde both have free OH groups that cannot reach any intramolecular acceptor, so they engage in intermolecular H-bonding. Para-hydroxybenzaldehyde is the standard answer.

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