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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

The following reaction involves a conjugate addition reaction followed by an intramolecular Claisen condensation. Write both steps, and show their mechanisms.

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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Using curved arrows to indicate the electron flow in each step, show how the base-catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone.

Predict the product(s) and provide the mechanism for each reaction below.
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