When a simple unsymmetrical ketone such as $C_3{H}_{6}O$ (propanone) is treated with base, which of the following best describes the enolates that can be formed?

• A. Two different enolates can be formed, one from deprotonation at each alpha carbon.
• B. No enolate is formed because ketones do not have acidic hydrogens.
• C. Only one enolate can be formed because both alpha carbons are equivalent.
• D. Three different enolates can be formed due to resonance structures.

Answer: (A)

Verified step by step guidance

1. Identify the structure of propanone (acetone), which is CH3-CO-CH3, a simple ketone with two methyl groups attached to the carbonyl carbon.
2. Recognize that alpha carbons are the carbons adjacent to the carbonyl carbon. In propanone, both alpha carbons are the two methyl groups on either side of the carbonyl.
3. Determine whether the alpha carbons are equivalent or not. Since both sides have identical methyl groups, the alpha carbons are equivalent.
4. Understand that enolate formation involves deprotonation of an alpha hydrogen by a base, generating a resonance-stabilized enolate ion.
5. Conclude that because the alpha carbons are equivalent, only one type of enolate can be formed by deprotonation at either alpha carbon, leading to the same enolate structure.