Predict the products formed when cyclohexanone reacts with the following reagents. (h) sodium acetylide, then mild H3O+

Verified step by step guidance

1. Identify the functional group in cyclohexanone, which is a ketone, and recognize that it can undergo nucleophilic addition reactions.
2. Understand that sodium acetylide (NaC≡CH) is a strong nucleophile due to the acetylide ion (C≡C⁻), which can attack electrophilic carbon centers.
3. Recognize that the carbonyl carbon in cyclohexanone is electrophilic and susceptible to nucleophilic attack by the acetylide ion.
4. Predict that the acetylide ion will attack the carbonyl carbon of cyclohexanone, leading to the opening of the carbonyl group and formation of an alkoxide intermediate.
5. Consider the role of mild H₃O⁺, which will protonate the alkoxide intermediate, resulting in the formation of an alcohol product with the acetylide group attached to the former carbonyl carbon.

Key Concepts

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in carbonyl compounds like ketones and aldehydes. In the case of cyclohexanone, sodium acetylide acts as a strong nucleophile, attacking the carbonyl carbon, leading to the formation of an alkoxide intermediate.

Acetylide Ion

The acetylide ion is a strong nucleophile derived from terminal alkynes, formed by deprotonating the alkyne with a strong base like sodium amide or sodium hydride. In this reaction, sodium acetylide provides a carbon nucleophile that can effectively add to the electrophilic carbonyl carbon of cyclohexanone, resulting in a new carbon-carbon bond.

Hydrolysis

Hydrolysis is a chemical reaction involving the addition of water to a compound, often leading to the breakdown of that compound. After the nucleophilic addition of sodium acetylide to cyclohexanone, mild H3O+ (acidic water) is used to protonate the alkoxide intermediate, converting it into an alcohol, which is the final product of the reaction.