In the following sequence of reactions, the major products B and C respectively are : [figure]
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Answer
(2) [figure]
Solution
[figure]
Na/dry ether reacts at the C–Br bond (weaker and more reactive than C–Cl), so Wurtz coupling joins two rings and gives A.
Mg/ether converts both C–Cl into C–MgCl, and D2O then replaces each MgCl by D, which gives B.
CoF2 exchanges Cl for F (Swarts reaction), which gives C.
Answer: (2)