Domanda del libro di testo
Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.
(b)
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25. Condensation Chemistry
Conjugate Addition
Scelta multipla
Predict the major, organic product for the following reaction.
A
B
C
D
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Identify the type of reaction: The reaction involves a conjugate addition (1,4-addition) of a Gilman reagent (Ph2CuLi) to an α,β-unsaturated ketone.
Recognize the role of the reagents: Ph2CuLi is a lithium diorganocuprate, which is known for performing 1,4-additions to α,β-unsaturated carbonyl compounds.
Determine the site of addition: In a 1,4-addition, the nucleophile (Ph group from Ph2CuLi) will add to the β-carbon of the α,β-unsaturated ketone, resulting in the formation of a new carbon-carbon bond.
Consider the stereochemistry: The addition of the Ph group to the β-carbon can lead to the formation of a chiral center. However, since the product is achiral, the stereochemistry is not a concern in this case.
Complete the reaction with a protonation step: After the addition of the Ph group, the enolate intermediate is protonated by the H⁺ quench, resulting in the final product, which is an achiral ketone with a phenyl group added to the β-position.
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