Assuming the Mechanistic Pathway for Each of the Following Reactions $\to$

Assuming the mechanistic pathway for each of the following reactions is predominately S_N1,which of these alkyl halide syntheses is predicted to occur at the greatest rate?

A) CH₃CH₂CH₂CH₂OH + HI $\to$
B) (CH₃) ₂CHCH₂OH + HBr $\to$
C) CH₃CHOHCH₂CH₃ + HCl $\to$
D) CH₃CHOHCH₂CH₃ + HBr $\to$
E) (CH₃) ₃COH + HI $\to$