Textbook Question
Show how the following products might be synthesized from suitable Michael donors and acceptors.
(e)
25. Condensation Chemistry
Michael Addition
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Determine the product in the following conjugated addition reaction.
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B
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D
Verified step by step guidance1
Identify the reactants: The reaction involves an α,β-unsaturated carbonyl compound and a nucleophile. The α,β-unsaturated carbonyl compound is the one with the ethoxy group (EtO) and a cyano group (CN) attached to the carbonyl carbon.
Recognize the reaction type: This is a conjugate addition reaction, also known as a Michael addition, where the nucleophile will add to the β-carbon of the α,β-unsaturated carbonyl compound.
Determine the nucleophile: In this reaction, the nucleophile is generated by the deprotonation of the ethyl cyanoacetate by sodium ethoxide (NaOEt) in ethanol (EtOH), forming an enolate ion.
Predict the addition: The enolate ion will attack the β-carbon of the α,β-unsaturated carbonyl compound, resulting in the formation of a new carbon-carbon bond.
Consider the final step: After the conjugate addition, the reaction mixture is treated with aqueous acid (H3O+), which will protonate the enolate ion to form the final product, a β-cyano carbonyl compound.
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