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Chapter 23: Q22P (page 777)

How would you prepare the following compound using a Robinson annulation reaction between a𝛃-diketone and an𝛂,𝛃 -unsaturated ketone? Draw the structures of both reactants and the intermediate Michael addition product

Short Answer

Expert verified

The given compound is formed by using the Michael addition reaction.

Step by step solution

01

Reaction

After analyzing the given compound, we find that this is a Michael addition reaction and the addition is taking place between two ketone compounds, and the formation of intermediate occurs as follows:

02

After heating the compound, a water molecule is removed and desired product is formed:

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Most popular questions from this chapter

Treatment of the minor product formed in the intramolecular aldol cyclization of 2,5-heptanedione (Problems 23-51 and 23-52) with aqueous NaOH converts it into the major product. Propose a mechanism to account for this base-catalyzed isomerization.

What product would you expect to obtain from the base treatment of

1,6-cyclo-decanedione?

Using curved arrows to indicate the electron flow in each step, show how the base-catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone.

In the mixed Claisen reaction of cyclopentanone with ethyl format, a much higher yield of the desired product is obtained by first mixing the two carbonyl components and then adding a base, rather than by first mixing base with cyclopentanone and then adding ethyl format. Explain.

What condensation products would you expect to obtain by treatment of the following substances with sodium ethoxide in ethanol?

(a)Ethyl butanoate

(b)Cycloheptanone

(c)3,7-Nonanedione

(d)3-Phenylpropanal
See all solutions

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