Which reagent cannot be used to prepare an alkyl halide from an alcohol?

The products $A$ and $B$ obtained in the following reactions,respectively,are
$3 ROH + PCl_3 \rightarrow 3 RCl + A$
$ROH + PCl_5 \rightarrow RCl + HCl + B$

Which among the following reactions does $NOT$ form alkyl halides?

$Ph-CH(OH)-CH_3 \xrightarrow{SOCl_2}$ major product

$2$-Bromobutane is obtained by the reaction of:

The major product in the following reaction sequence is: