Questions: Which is the thermodynamic enolate of 2-methylcyclohexanone?
I
II
III
IV
Multiple Choice
IV
Transcript text: Which is the thermodynamic enolate of 2-methylcyclohexanone?
I
II
III
IV
Multiple Choice
IV
Solution
Solution Steps
Step 1: Identify the alpha carbons
The alpha carbons are the carbon atoms adjacent to the carbonyl group (C=O). In 2-methylcyclohexanone, there are two alpha carbons: one bearing the methyl group, and the other on the other side of the carbonyl group.
Step 2: Determine the possible enolates
An enolate is formed by deprotonation of an alpha carbon, forming a double bond between the alpha carbon and the carbonyl carbon. The thermodynamic enolate is the more substituted, more stable enolate. In this case, the more substituted enolate is the one with the double bond formed between the more substituted alpha carbon (the one bearing the methyl group) and the carbonyl carbon.
Step 3: Identify the correct structure
Structure I corresponds to the enolate formed by deprotonation at the less substituted alpha carbon.
Structure II corresponds to the enolate formed by deprotonation at the more substituted alpha carbon (the one with the methyl group). This is the thermodynamic enolate.
Structures III and IV are not enolates.