A mixture of bromobenzene, 1-bromo-4-methylbenzene and bromomethane (all in equal amount) is treated with sodium metal in dry ether. Assuming every possible coupling of two different or identical groups occurs, how many different coupled products are formed?

Answer: D

Three different groups (phenyl, 4-methylphenyl and methyl) can couple in pairs, with repetition allowed: 3 identical (biphenyl, 4,4'-dimethylbiphenyl, ethane) + 3 mixed (4-methylbiphenyl, toluene, 1,4-dimethylbenzene) = 6 combinations (n(n+1)/2 with n = 3).

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