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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

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

Tautomerism of ketoester:

Attack of enol on iminium ion:

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Most popular questions from this chapter

The aldol reaction is catalyzed by acid as well as the base. What is the reactive nucleophile in the acid-catalyzed aldol reaction? Propose a mechanism.

The bicyclic ketone shown below does not undergo aldol self-condensation even though it has two hydrogen atoms. Explain.

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

What product would you obtain from a base-catalyzed Michael reaction of 2,4-pentanedione with each of the following α-β unsaturated acceptors?

(a) 2-Cyclohexenone

(b) Propenenitrile

What enone product would you expect from aldol condensation of each of the following compounds?

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

Short Answer

Step by step solution

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

Tautomerism of ketoester:

Attack of enol on iminium ion:

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Most popular questions from this chapter

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