Step 1: Understand the nature of reactions of alcohols.
Alcohols can react either by breaking the O–H bond or the C–O bond depending on the reagent used.
Step 2: Analyze reaction with acid anhydride.
In reaction with acid anhydride, alcohol behaves as a nucleophile through oxygen atom and the hydrogen of –OH is removed.
Thus, the O–H bond is broken and ester is formed.
Step 3: Analyze other options.
(B) Thionyl chloride: Breaks the C–O bond to form alkyl chloride.
(C) Lucas reagent: Also involves cleavage of C–O bond.
(D) Phosphorus halides: Replace –OH by halogen by breaking C–O bond.
Step 4: Conclusion.
Only reaction with acid anhydride involves breaking of O–H bond.