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Chapter 23: Q25E (page 783)

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

Short Answer

Expert verified

The molecule is formed by the aldol reaction.

Step by step solution

01

Product

The given product is,

02

Reactant

The reaction for the formation of the given product by aldol reaction is,

Thus, the reactant used for the production of given product is,

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Most popular questions from this chapter

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.

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 Darzens reaction involves a two-step, base-catalyzed condensation of ethyl chloroacetate with a ketone to yield an epoxy ester. The first step is a carbonyl condensation reaction, and the second step is an SN2 reaction. Write both steps, and show their mechanisms.

1-Butanol is prepared commercially by a route that begins with an aldol reaction. Show the steps that are likely to be involved.

The major product formed by intramolecular aldol cyclization of 2,5-heptanedione (Problem 23-51) has two singlet absorptions in the 1H NMR spectrum, at 1.65 d and 1.90 d, and has no absorptions in the range 3 to 10 d. What is its structure?
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