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Chapter 23: Q23-20P (page 775)

Show how you might use an enamine reaction to prepare each of the following compounds:

Short Answer

Expert verified

These are carbon nucleophiles which are very useful in biological chemistry. Enamines are readily prepared by a reaction between a ketone and a secondary amine:

Step by step solution

01

Enamines:

These are carbon nucleophiles which are very useful in biological chemistry. Enamines are readily prepared by a reaction between a ketone and a secondary amine:

02

Formation of the first product from enamine:

03

Formation of second product from enamine:

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Most popular questions from this chapter

Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction.

(a) Trimethyl acetaldehyde

(b) Cyclobutanone

(c) Benzophenone (diphenyl ketone)

(d) 3-Pentanone

(e) Decanal

(f) 3-Phenyl-2-propenal

The first step in the citric acid cycle of food metabolism is reaction of oxaloacetate with acetyl CoA to give citrate. Propose a mechanism, using acid or base catalysis as needed.

The compound known as Hagemannโ€™s ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation.

(a)The first step is an aldol-like condensation between ethyl acetoacetate and formaldehyde to yield an ฮฑ,ฮฒ-unsaturated product. Write the reaction, and show the structure of the product.

(b)The second step is a Michael reaction between ethyl acetoacetate and the unsaturated product of the first step. Show the structure of the product.

As shown in Figures 23-4, the Claisen reaction is reversible. That is, a๐›ƒ-keto ester can be cleaved by base into two fragments. Using curved arrows to indicate electron flow, show the mechanism by which this cleavage occurs.

The Knoevenagel reaction is a carbonyl condensation reaction of an ester with an aldehyde or ketone to yield an ฮฑ,ฮฒ-unsaturated product. Show the mechanism for the Knoevenagel reaction of diethyl malonate with benzaldehyde.
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