JEE Advanced levelSingle correct optionDifficulty 3 of 3hx162
A mixture of bromobenzene and 1-bromo-4-methylbenzene (1 : 1) is treated with sodium in dry ether (Fittig reaction). Counting only the aromatic coupling products, the number of different compounds formed (biaryls) is
A4
B6
C3
D2
Answer: C
Two aryl radicals/organosodium species can combine in three ways: Ph−Ph (biphenyl), 4-CHX3CX6HX4−CX6HX4−4-CHX3 (4,4′-dimethylbiphenyl) and the cross product 4-CHX3CX6HX4−CX6HX5 (4-methylbiphenyl). Hence 3.