(a)
The –OH group of alcohol or the –COOH group of a carboxylic acid is replaced by –Cl using phosphorus pentachloride $(i.e.,PCl_{5})$
$ROH + PCl_{5} \rightarrow RCl + POCl_{3} + HCl$
alcohol
$RCOOH + PCl_{5} \rightarrow RCOCl + {POCl}_{3} + HCl$
acid