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Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 20, Problema 43a

Predict the product of the following reactions.
(a) Chemical reaction diagram showing reactants and conditions for Robinson Annulation, including NaOH and ethanol.

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Identify the reaction type: The reaction involves a diketone and an α,β-unsaturated ketone in the presence of a base (NaOH) and heat, suggesting a Michael addition followed by an intramolecular aldol condensation.
Michael addition: The enolate ion formed from the diketone will attack the β-carbon of the α,β-unsaturated ketone, resulting in a 1,4-addition. This step forms a new carbon-carbon bond.
Intramolecular aldol condensation: The newly formed compound will undergo an intramolecular aldol reaction. The enolate ion generated from the remaining ketone group will attack the carbonyl carbon of the other ketone group, forming a cyclic β-hydroxy ketone.
Dehydration: The β-hydroxy ketone will undergo dehydration (loss of water) to form an α,β-unsaturated ketone, resulting in a conjugated cyclic product.
Consider stereochemistry: Analyze the stereochemistry of the final product, as the formation of new chiral centers during the reaction may lead to stereoisomers.

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