Organic Chemistry 2 · Hydrolysis and esterification
Benzoyl chloride and water: products of hydrolysis
Conditions: Benzoyl chloride stirred with water at room temperature, no acid or base added.
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The question
Benzoyl chloride is stirred with water. What are the products?
Reveal the answer and explanation
Answer and explanation
Correct answer Benzoic acid and HCl
Correct: water replaces chloride at the acyl carbon.
Not this one Benzaldehyde and HOCl
Hydrolysis is a substitution at the acyl carbon, not a redox reaction; the carbon stays at the acid oxidation level.
Not this one Benzoic anhydride and HCl only
An anhydride can form if benzoate meets more acid chloride, but with water in excess the product is the acid.
Not this one Chlorobenzene and formic acid
The ring–carbonyl bond is not broken; the C–Cl bond is.
Worked solution
Water adds to the very electrophilic acyl chloride carbonyl, and the tetrahedral intermediate expels chloride, the best leaving group of all acid derivatives. Loss of a proton gives benzoic acid, and the chloride and proton form HCl. No catalyst is needed: chlorine donates almost nothing into the C=O, so even neutral water reacts readily.
What you'll practice
Predict the products when an acyl chloride is hydrolysed by water alone.
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