The aryl bromide shown is mixed with bromomethane and treated with sodium in dry ether (Wurtz-Fittig conditions). How many distinct coupled products are possible, counting the cross-product and both homo-coupled products?

Answer: C

The compound shown is bromobenzene. The three possible couplings are aryl-aryl (biphenyl), aryl-methyl (toluene, the cross product) and methyl-methyl (ethane). These are three different compounds, so the answer is 3.

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