Solution

ID: past-exam-of-the-chemistry-b-course-of-the-university-of-cambridge/2021/paper-1/b5/b/i/solution

Two molecules of the carboxylic acid form a cyclic carboxylic-acid dimer. Let Ar denote the meta-methylphenyl group. One molecule donates its OH hydrogen to the other's carbonyl oxygen, and the second donates back:
The two contacts close an eight-membered hydrogen-bonded ring, shown explicitly below.
Both molecules therefore act once as hydrogen-bond donor and once as hydrogen-bond acceptor, giving two O–H···O=C contacts. This is the conventional self-complementary dimer motif; the schematic is not a prediction of every weaker contact in an unprovided crystal structure.
Figure 1.
Original hydrogen-bonding structures for the two pure-compound homodimers
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