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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:

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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:

Formation of the first product from enamine:

Formation of second product from enamine:

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Most popular questions from this chapter

The Stork enamine reaction and the intramolecular aldol reaction can be carried out in sequence to allow the synthesis of cyclohexanones. For example, the reaction of the pyrrolidine enamine of cyclohexanone with 3-buten-2-one, followed by enamine hydrolysis and base treatment, yields the product indicated. Write each step, and show the mechanism of each.

The third and fourth steps in the synthesis of Hagemann’s ester from ethyl acetoacetate and formaldehyde (Problem 23-71) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.

The following reaction involves two successive intramolecular Michael reactions. Write both steps, and show their mechanisms.