Ch23. Carbonyl Condensation Reactions The Aldol Addition and Condensation - Aldehydes & Ketones react in basic solution (NaOH) to yield Aldol; aldehyde (or ketone) + alcohol (Addition) Dehydration (-H2O) of Aldol product yields a,ß-unsaturated ketones, aldehydes (Condensation) NaOH - Mixed Aldol Reactions: possibly leads to a mixture CHO + - Intramolecular Aldol reactions NaOH/H₂O Heat ? 3 Michael Addition: a,ß-unsaturated ketones/aldehydes react with enolate (nucleophile) as 1,4-(conjugate) addition - Robinson Annulation: Enolate-Michael addition, followed by Intramolecular Aldol Condensation Base 1) NaOCH₂CH₂ 2) H+ - Dieckmann Cyclization: Intramolecular Claisen Condensation The Claisen Condensation - Esters react with strong base (NaOR, LDA, NAH) to yield Claisen product; 2 esters react and one alcohol leaves Mixed Claisen Reactions
Ch23. Carbonyl Condensation Reactions The Aldol Addition and Condensation - Aldehydes & Ketones react in basic solution (NaOH) to yield Aldol; aldehyde (or ketone) + alcohol (Addition) Dehydration (-H2O) of Aldol product yields a,ß-unsaturated ketones, aldehydes (Condensation) NaOH - Mixed Aldol Reactions: possibly leads to a mixture CHO + - Intramolecular Aldol reactions NaOH/H₂O Heat ? 3 Michael Addition: a,ß-unsaturated ketones/aldehydes react with enolate (nucleophile) as 1,4-(conjugate) addition - Robinson Annulation: Enolate-Michael addition, followed by Intramolecular Aldol Condensation Base 1) NaOCH₂CH₂ 2) H+ - Dieckmann Cyclization: Intramolecular Claisen Condensation The Claisen Condensation - Esters react with strong base (NaOR, LDA, NAH) to yield Claisen product; 2 esters react and one alcohol leaves Mixed Claisen Reactions
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Chapter 23: Carbonyl Condensation Reactions**
**The Aldol Addition and Condensation**
- **Aldehydes & Ketones** react in basic solution (NaOH) to yield an Aldol; the reaction involves an aldehyde (or ketone) and an alcohol (Addition).
- Dehydration (-H₂O) of the Aldol product yields α,β-unsaturated ketones and aldehydes (Condensation).
- **Diagram 1:** Shows a ketone reacting with NaOH to form an Aldol.
- **Mixed Aldol Reactions:** These reactions can potentially lead to a mixture of products.
- **Diagram 2:** Displays an aldehyde reacting with a ketone in the presence of NaOH and heat, leading to an unspecified product (?).
- **Intramolecular Aldol Reactions:** These involve reactions occurring within the same molecule.
- **Michael Addition:** This involves α,β-unsaturated ketones/aldehydes reacting with an enolate (nucleophile) as a 1,4-(conjugate) addition.
- **Robinson Annulation:** This is a two-step reaction involving an Enolate-Michael addition followed by intramolecular Aldol Condensation.
- **Diagram 3:** Illustrates an enolate reacting with a ketone and a base to form an annulated product.
**The Claisen Condensation**
- **Esters** react with a strong base (NaOR, LDA, NaH) to yield a Claisen product; two esters react, and one alcohol is removed.
- **Mixed Claisen Reactions:**
- **Diagram 4:** Demonstrates Claisen Condensation where two esters react using NaOCH₂CH₃ followed by an acid (H⁺) to form a product.
- **Dieckmann Cyclization:** An intramolecular Claisen Condensation process.
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Step 1: Carbonyl condensation reaction
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