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Chapter 24: Q.13. (page 962)

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

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01

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.

02

Explanation for the mechanism

In the first step of the reaction, EtO-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,EtO-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

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Most popular questions from this chapter

Question: 4-Methylpyridine reacts with benzaldehyde (C6H5CHO)in the presence of a base to form A.

(a) Draw a stepwise mechanism for this reaction.

(b) Would you expect 2-methylpyridine or 3-methylpyridine to undergo a similar type of condensation reaction? Explain why or why not.

Question: Draw the product of each Robinson annulation from the given starting materials using OHin H2Osolution.

Question: Isophorone is formed from three molecules of acetone [CH32=CO]in the presence of base. Draw a mechanism for this process.

Question: What product is formed when each pair of compounds is treated with NaOEt in ethanol?

Question: Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.
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