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MCAT Chemistry Practice Question – Amines

If hexanamide is treated with ethanol, what would be the expected products?

A. Hexanamide and water

B. Ethyl hexanoate and an amine

C. Hexanoic acid and an amine

D. No reaction



An amine group is a much stronger nucleophile than ethanol, and thus has very low propensity to leave the amide under these conditions. Another way to look at this could be that amides are significantly more stable than esters, so a reaction to form a less stable molecule would be unlikely without sufficiently specific conditions. Therefore, D. is the correct answer.

A. Hexanamide and water: incorrect. There is no reason to expect spontaneous transformation of ethanol into water.

B. Ethyl hexanoate and an amine; incorrect.

These could be the products of an acyl substitution reaction initiated by ethanol attacking the carbonyl carbon. However, since the amine produced would be a much better nucleophile than ethanol, much harsher conditions would be required to favor formation of the ester (perhaps an excess of ethanol with high heat and acid).

C. Hexanoic acid and an amine; incorrect. This sort of product might be possible under high heat with aqueous acid added, but the alcohol starting material is unaccounted for and water is not mentioned.


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