9. Which of the following reaction sequences would convert 2-butanol into 2-deuterobutane?
(A) 1. H2SO4, heat 2. BD3 in THF, then H2O2, NaOH
(B) 1. H2SO4, heat 2. D2, Pd/C
(C) 1. PBr3 2. Mg/ether, then D2O
(D) 1. PBr3 2. NaOD, then D2O
(E) 1. PBr3 2. NaD in hexane