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Enols and Enolates

Topic Review on "Title":

Background Information for Enols and Enolates
An enol contains a OH attached to a C=C.  An enolate ion is a structure in which a O- is next to C=C or C=O is next to C-.  Tautomerize is moving an electron pair to form another double bond, along with the movement of a H.  Alpha substitution is replacement of H on alpha carbon, which is C next to C=O.  Carbonyl condensation is a reaction in which the electrophile is another carbonyl compound. 

Halogenation of Carbonyl Compounds
Ketones and aldehydes are halogenated on the α-carbon in the presence of acid to form α-halo ketones and aldehydes.  Ketones and aldehydes are halogenated on the α-carbon in the presence of base to form α-halo ketones and aldehydes.  In the presence of excess base and excess halogen, methyl ketones form carboxylate anions and haloforms in the haloform reaction.  In the Hell-Volhard-Zelinsky reaction, carboxylic acids are halogenated with phosphorus trihalides to yield α-halo carboxylic acids.

Alkylation of Carbonyl Compounds
Ketones and aldehydes can be treated with lithium diisopropylamide (LDA), followed by an alkyl halide, to yield α-alkyl ketones and aldehydes. Ketones and aldehydes are reacted with a secondary amine and an alkyl halide, followed by acidification to yield α-alkyl ketones and aldehydes.

Condensation of Carbonyl Compounds
Ketones and aldehydes undergo aldol condensation, in the presence of base, to form β-hydroxy aldehydes and ketones (aldols), which lose water to form α,β-unsaturated aldehydes and ketones.  Esters condense in the presence of base, followed by hydrolysis, to yield β-ketoesters.

Alkylation of Dicarbonyl Compounds
Diethyl malonate is reacted with base, alkylated, then hydrolyzed to yield a substituted acetic acid, carbon dioxide, and ethanol.  Ethyl acetoacetate is treated with base, alkylated, then hydrolyzed to yield a substituted acetone, carbon dioxide, and ethanol.


Rapid Study Kit for "Title":
Flash Movie Flash Game Flash Card
Core Concept Tutorial Problem Solving Drill Review Cheat Sheet

"Title" Tutorial Summary :
The background information for enols and enolates include definitions and structures.  The halogenation of carbonyl compounds include halogenation of ketones and aldehydes in the presence of acid or base, the haloform reaction, and the Hell-Volhard-Zelinsky reaction are discussed.  The alkylation of carbonyl compounds can be done in the presence of lithium diisopropyl amide or with enamines.  Carbonyl compounds can be condensed through the aldol condensation or the Claisen ester condensation.  Dicarbonyl compounds can be alkylated through the malonic ester synthesis and the acetoacetic ester synthesis.

Tutorial Features:

This tutorial provides the comprehensive coverage of the chapter with easy introduction and simple illustration. It features:

  • Concept map showing interconnections of new concepts in this tutorial and those previously introduced.
  • Definition slides introduce terms as they are needed.
  • Visual representation of concepts.
  • Use of colors to emphasis points.
  • Detailed stepwise explanations and animations of reactions and mechanisms.
  • Examples worked out step-by-step throughout the tutorial.
  • A concise summary is given at the conclusion of the tutorial.

"Title" Topic List:

Background Information for Enols and Enolates

  • Definitions
  • Structures

Halogenation of Carbonyl Compounds

  • Halogenation of Ketones and Aldehydes in the Presence of Acid
  • Halogenation of Ketones and Aldehydes in the Presence of Base
  • Haloform Reaction
  • Hell-Volhard-Zelinsky Reaction

Alkylation of Carbonyl Compounds

  • Alkylation of LDA
  • Alkylation of Enamines

Condensation of Carbonyl Compounds

  • Aldol Condensation
  • Claisen Ester Condensation

Alkylation of Dicarbonyl Compounds

  • Malonic Ester Synthesis
  • Acetoacetic Ester Synthesis


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