What is the product of a reaction between an acyl chloride and a secondary alcohol?
It's a bit tricky because there's probably a reagent that's missing. You might add DMAP or triethylamine to this reaction which would further activate the acyl chloride. But the alcohol oxygen is the most nucleophilic moiety in this reaction. The most electrophilic moiety is the carbonyl group, especially since it's activated by the electron withdrawing chlorine.

Thus we would predict that a standard acylation (a carbonyl reaction) will take place where we add a nucleophile to the carbon of a carbonyl group. After which, reformation of the carbonyl group will result in kicking out a chloride anion. Finally, a very fast proton transfer will take place that breaks the O-H bond you are referring to. Notice that this is really an after thought and not really the key point of this reaction.

Take a look at the mechanism for the reaction in your textbook (or here).