An acid chloride treated with ammonia in ethanol yields which product?

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Multiple Choice

An acid chloride treated with ammonia in ethanol yields which product?

Acid chlorides are highly reactive toward nucleophiles, so ammonia acts as the nucleophile and attacks the carbonyl carbon. The chloride leaves, giving a tetrahedral intermediate that collapses to form a primary amide (RCONH2). The reaction also produces HCl, which is neutralized by excess ammonia to form ammonium chloride, driving the reaction forward. Because the attacking nitrogen is NH3, the amide ends up with two hydrogens on the nitrogen, i.e., a primary amide. If a different amine were used, a secondary amide would form; if hydrolysis or reaction with alcohol predominated, other products like carboxylic acid or an ester could arise, but ammonia in this medium preferentially yields the primary amide.

Acid chlorides are highly reactive toward nucleophiles, so ammonia acts as the nucleophile and attacks the carbonyl carbon. The chloride leaves, giving a tetrahedral intermediate that collapses to form a primary amide (RCONH2). The reaction also produces HCl, which is neutralized by excess ammonia to form ammonium chloride, driving the reaction forward. Because the attacking nitrogen is NH3, the amide ends up with two hydrogens on the nitrogen, i.e., a primary amide. If a different amine were used, a secondary amide would form; if hydrolysis or reaction with alcohol predominated, other products like carboxylic acid or an ester could arise, but ammonia in this medium preferentially yields the primary amide.

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