JEE Advanced levelSingle correct optionDifficulty 3 of 3hx087
1-Bromobutane is treated with 2 equivalents of lithium metal in dry ether to give X. Two equivalents of X react with CuI to give the Gilman reagent Y, and Y then reacts with CHX3I to give the hydrocarbon Z. Z is
Apentane
Boctane
Chexane
Dbutane
Answer: A
X is butyllithium; two BuLi with CuI give lithium dibutylcuprate (CX4HX9)X2CuLi. A Gilman reagent transfers one alkyl group to an alkyl halide in a coupling reaction: BuX2CuLi+CHX3IBu−CHX3+BuCu+LiI. The new hydrocarbon CHX3CHX2CHX2CHX2CHX3 is pentane.