4. Assuming the mechanistic pathway for each of the following reactions is predominantly SN1, which of these alkyl halide syntheses is predicted to occur at the greatest rate?
a) CH3CH2CH2CHOH + HI
b) (CH3)2CHOH + HBr
c) CH3CHOHCH2CH3 + HCl
d) CH3CHOHCH2CH3 + HBr
e) (CH3)2COH + HI