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Chapter 23: Q3P (page 759)

What enone product would you expect from aldol condensation of each of the following compounds?

Short Answer

Expert verified

ENONEcontains 伪-尾unsaturated carbonyl compound having alkene which is conjugated to ketone in the same compound.

Step by step solution

01

(a) first product is:

02

(b) second product is:


03

(c)third product is:

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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.

The bicyclic ketone shown below does not undergo aldol self-condensation even though it has two hydrogen atoms. Explain.

The following molecule was formed by an intramolecular aldol reaction. What dicarbonyl precursor was used for its preparation?

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

The Mannich reaction of a ketone, an amine, and an aldehyde is one of the few three-component reactions in organic chemistry. Cyclohexanone, for example, reacts with dimethylamine and acetaldehyde to yield an amino ketone. The reaction takes place in two steps, both of which are typical carbonyl-group reactions.

(a)The first step is reaction between the aldehyde and the amine to yield an intermediate iminium ion R2C=NR2+plus water. Propose a mechanism, and show the structure of the intermediate iminium ion.

(b)The second step is reaction between the iminium ion intermediate and the ketone to yield the final product. Propose a mechanism.
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