Which reagents form an ester from an acid chloride?

Master NCEA Level 3 Organic Chemistry Reaction Schemes. Prepare with multiple choice questions, complete with hints and detailed explanations. Ace your exam with our comprehensive tools!

Multiple Choice

Which reagents form an ester from an acid chloride?

When forming esters from an acid chloride, the essential step is nucleophilic acyl substitution: a nucleophile attacks the carbonyl carbon and chloride leaves. The nucleophile in this case is an alcohol, which donates its lone pair to the acyl chloride, displacing chloride and giving an ester plus HCl. That’s why the combination of an acid chloride with an alcohol forms an ester: RCOCl + R'OH → RCOOR' + HCl. Water, on the other hand, tends to hydrolyze the acid chloride, producing the carboxylic acid rather than an ester. Ammonia would attack to form an amide (RCONH2) instead of an ester. A base alone doesn’t provide the nucleophile needed to form an ester; it may help by deprotonating the alcohol to give a stronger nucleophile, but the actual ester formation requires the alcohol itself.

When forming esters from an acid chloride, the essential step is nucleophilic acyl substitution: a nucleophile attacks the carbonyl carbon and chloride leaves. The nucleophile in this case is an alcohol, which donates its lone pair to the acyl chloride, displacing chloride and giving an ester plus HCl.

That’s why the combination of an acid chloride with an alcohol forms an ester: RCOCl + R'OH → RCOOR' + HCl. Water, on the other hand, tends to hydrolyze the acid chloride, producing the carboxylic acid rather than an ester. Ammonia would attack to form an amide (RCONH2) instead of an ester. A base alone doesn’t provide the nucleophile needed to form an ester; it may help by deprotonating the alcohol to give a stronger nucleophile, but the actual ester formation requires the alcohol itself.

More practice questions