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Due to hydrogen bonding, which of the following molecules does NOT form a ring structure either in its monomeric form or in its dimeric form?

1. CH3COOH
2. Salicylaldehyde
3. C6H5OH (Phenol)
4. CCl3CHO. H2O (Chloral hydrate)

Correct answer: C6H5OH (Phenol)

Solution

CH3COOH: classic 8-membered cyclic dimer via O-H...O=C hydrogen bonds — forms ring. Salicylaldehyde (2-hydroxybenzaldehyde): intramolecular H-bond between OH and CHO forms a 5-membered ring — forms ring. CCl3CHO.H2O (chloral hydrate = CCl3CH(OH)2): the two OH groups can participate in a cyclic dimeric H-bond — forms ring. Phenol (C6H5OH): the OH group can H-bond intermolecularly but the symmetric dimer or monomer has no geometry that closes into a ring. Phenol does not form a cyclic H-bonded structure.

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