Organic Chemistry MCAT Practice Exam

What product is formed when adding water to an enamine?

1. Alcohol

2. Carboxylic acid

3. Carbonyl compound

4. Hemiacetal

The correct answer is: Carbonyl compound

When water is added to an enamine, the product formed is a carbonyl compound. Enamines are derivatives of carbonyl compounds in which an amino group is bonded to one of the carbon atoms involved in the carbonyl structure. Upon hydrolysis, the enamine undergoes a rearrangement that ultimately leads to the regeneration of the carbonyl moiety, typically as an aldehyde or ketone, depending on the specific enamine being hydrolyzed. The reaction is often facilitated by the addition of water, which acts as a nucleophile, attacking the electrophilic carbon atom of the enamine. This results in the breaking of the C=N bond and the formation of a carbonyl compound, typically accompanied by the release of an amine as a byproduct. As a result, the process yields the carbonyl compound that is characteristic of the parent structure from which the enamine was derived. Understanding the reactivity of enamines and their transformation in hydrolysis is fundamental in organic chemistry, especially in discussions about nucleophilic addition reactions and the roles of different functional groups.