# What is the product of a reaction between an acyl chloride and a secondary alcohol?

For the following two reactants, I want to predict the major product.

I would have thought the second reactant $\ce{CH3CH(OH)CH3}$ splits into $\ce{CH3CHCH+}$ and $\ce{OH-}$ , and the $\ce{OH-}$ would replace the $\ce{Cl-}$ in the first reactant $\ce{Phenyl-COCl}$, giving B. My main reason for thinking this would occur is that I always see e.g. water form $\ce{H+ and OH-}$.

However, the answer is C. The $\ce{CH3CH(OH)CH3}$ gives up only its $\ce{H+}$, and the rest of it joins $\ce{Phenyl-COCl}$ to form C.

How do I predict which atom(s) will leave/join? And for this particular question, how do I know the bond in the 2nd reactant cleaves at O-H not at C-OH?

• I don't understand what you're asking. The answer is C. Why or what are you asking about D? – Zhe Feb 15 '17 at 3:18
• Sorry! Typo. I am asking why the H+ leaves the CH3CH(OH)CH3, leaving the CH3CH(O)CH3- to swap with the Cl- (giving C). Rather than CH3CH(OH)CH splitting into CH3CHCH+ and OH-, and the OH- replacing the Cl- in the first reactant. – K-Feldspar Feb 15 '17 at 3:20
• In other words, why does the 2nd reactant split at the O-H bond and not the C-OH bond. Thank you. Let me know if my question still doesn't make sense and I will try and re-word it. – K-Feldspar Feb 15 '17 at 3:23