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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 43b

Predict the product of the following reactions.
(b) Chemical reaction diagram showing reactants and conditions for Robinson Annulation.

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Identify the reaction type: The presence of KOH, H2O, and heat suggests a Claisen condensation reaction, which typically involves the formation of a β-keto ester or β-diketone.
Analyze the reactants: The first reactant is an ethyl ester of a cyclic carboxylic acid, and the second reactant is an α,β-unsaturated ketone. The ester will undergo deprotonation at the α-carbon by the strong base KOH.
Form the enolate ion: The base (KOH) will deprotonate the α-carbon of the ester, forming an enolate ion. This enolate is nucleophilic and will attack the electrophilic carbonyl carbon of the α,β-unsaturated ketone.
Perform the nucleophilic attack: The enolate ion attacks the carbonyl carbon of the α,β-unsaturated ketone, leading to the formation of a new carbon-carbon bond. This step results in the formation of a β-keto ester intermediate.
Complete the reaction: The intermediate undergoes intramolecular rearrangement and elimination of the ethoxide ion, resulting in the formation of the final product, which is a β-diketone. The reaction is driven to completion by the heat provided.

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