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Ch22. Carbonyl Alpha-Substitution Reactions - Keto-enol Tautomerism Carbonyl compounds react with base to create enolate - Halogenation - Alkylation onto a-Carbon of ketones and aldehydes 1.LDA (or NaH) 2.RX 1) LDA 2) Br

Ch22. Carbonyl Alpha-Substitution Reactions - Keto-enol Tautomerism Carbonyl compounds react with base to create enolate - Halogenation - Alkylation onto a-Carbon of ketones and aldehydes 1.LDA (or NaH) 2.RX 1) LDA 2) Br

Chemistry
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Chapter 22: Carbonyl Alpha-Substitution Reactions** - **Keto-Enol Tautomerism** - This concept involves the equilibrium between keto (carbonyl) and enol (alcohol) forms of carbonyl compounds, which is fundamental in understanding their reactivity. - **Reactivity of Carbonyl Compounds with Bases** - When carbonyl compounds are treated with a base, they form enolates. These reactive intermediates are crucial in substitution reactions. - **Types of Alpha-Substitution Reactions:** - **Halogenation** - Involves the substitution of a hydrogen atom on the alpha-carbon with a halogen. - **Alkylation** - Refers to the addition of an alkyl group to the alpha-carbon. This is typically done in the presence of strong bases and an alkyl halide (RX). **Diagram Explanation:** The diagram illustrates a two-step reaction sequence for the alkylation of a carbonyl compound: 1. **Formation of Enolate:** - Begin with a cyclic ketone. Treatment with a strong base like Lithium Diisopropylamide (LDA) or Sodium Hydride (NaH) generates the enolate ion by deprotonating the alpha carbon. 2. **Alkylation Reaction:** - The enolate ion reacts with an alkyl halide (shown here as a bromide) in a nucleophilic substitution reaction, resulting in the alkylation of the alpha-carbon.
Transcribed Image Text:**Chapter 22: Carbonyl Alpha-Substitution Reactions** - **Keto-Enol Tautomerism** - This concept involves the equilibrium between keto (carbonyl) and enol (alcohol) forms of carbonyl compounds, which is fundamental in understanding their reactivity. - **Reactivity of Carbonyl Compounds with Bases** - When carbonyl compounds are treated with a base, they form enolates. These reactive intermediates are crucial in substitution reactions. - **Types of Alpha-Substitution Reactions:** - **Halogenation** - Involves the substitution of a hydrogen atom on the alpha-carbon with a halogen. - **Alkylation** - Refers to the addition of an alkyl group to the alpha-carbon. This is typically done in the presence of strong bases and an alkyl halide (RX). **Diagram Explanation:** The diagram illustrates a two-step reaction sequence for the alkylation of a carbonyl compound: 1. **Formation of Enolate:** - Begin with a cyclic ketone. Treatment with a strong base like Lithium Diisopropylamide (LDA) or Sodium Hydride (NaH) generates the enolate ion by deprotonating the alpha carbon. 2. **Alkylation Reaction:** - The enolate ion reacts with an alkyl halide (shown here as a bromide) in a nucleophilic substitution reaction, resulting in the alkylation of the alpha-carbon.
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