Which of the Following Could Not Be Used to Synthesize $\rightarrow$

Which of the following could not be used to synthesize 2-bromopentane efficiently?

A) 1-Pentene + HBr $\rightarrow$
B) 2-Pentene + HBr $\rightarrow$
C) 2-Pentanol + HBr $\rightarrow$
D) 2-Pentanol + PBr₃ $\rightarrow$
E) All of the above would afford good yields of 2-bromopentane.