Question

Question: Draw a stepwise mechanism for the conversion of heptane-2,6-dione to 3-methylcyclohex-2-enone with NaOEt, EtOH.

Short answer

Answer

Step-by-step solution

Aldol reaction

Aldol reaction in the presence of base is termed as base-catalyzed aldol reaction. It is performed under NaOEt, EtOH and is a reversible reaction.

Explanation for the mechanism

In the first step of the reaction, $Et{O}^{-}$from NaOEt abstracts an alpha hydrogen to create a nucleophilic carbon center. Then, the intermolecular attack takes place to form a six-membered ring.

Negative charge on oxygen abstracts proton from EtOH to form hydroxyl group in the compound. Further,$Et{O}^{-}$abstracts proton to create negative charge. The rearrangement takes place to form 3-methylcyclohex-2-enone.

The mechanism is shown below:

Mechanism of the reaction