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Chapter 23: Q47E (page 783)

Propose a mechanism to account for the following reaction of an enamine with an alkyl halide:

Short Answer

Expert verified

The above reaction is the Stork Enamine Alkylation reaction.

Step by step solution

01

The reaction is start with the Sn2 mechanism by the displacement of Br- ion from enamine:

02

Tautomerism of ketoester:

03

Attack of enol on iminium ion:

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Most popular questions from this chapter

Ethyl dimethyl acetoacetate reacts instantly at room temperature when treated with ethoxide ion to yield two products, ethyl acetate, and ethyl 2-methyl propanoate. Propose a mechanism for this cleavage reaction.

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

In contrast to the rapid reaction shown in Problem 23-60, ethyl acetoacetate requires a temperature over 150 °C to undergo the same kind of cleavage reaction. How can you explain the difference in reactivity?

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

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