TAILIEUCHUNG - Lecture Organic chemistry - Chapter 18: Enols, enolates, enals, and enones

Chapter 18 provides knowledge of enols, enolates, enals, and enones. The main contents of this chapter include all of the following: Keto-enol equilibria, aldol condensation, intramolecular aldol, preparation,.and other contents. | Chapter 18: Enols, Enolates, Enals, and Enones α-Hydrogens in carbonyl compounds are acidic 12/13/2014 1 Deprotonation of a carbonyl compound: Stoichiometric deprotonation: KH, LDA Compare: propene ~40 Dominant form Enolates: “Oxaallyls” Acetone enolate Note: RLi and RMgX usually add to carbonyl Equilibrium deprotonation: NaOH, NaOR Reactivity: Ambident, attack on either O or C: Alkylation on C is dominant Kinetic protonation on O, followed by tautomerism Tautomerization Enolate formation can be regioselective Traces of acid (free amine, slight excess of ketone) give equilibration to more stable enolate Keto-Enol Equilibria H+ or –OH cat. K <<1 usually We often don’t need stoichiometric enolate formation: Acid or base forms enols or enolates in equilibrium concentrations, sufficient for many further transformations. H+ or –OH cat. Worse, because CH3 stabilizes keto form “Keto form” “Enol form” Mechanisms of enol to keto tautomerization (and the reverse): Acid-catalyzed Base-catalyzed

• Hoá học
• Organic chemistry
• Lecture Organic chemistry
• Hóa học hữu cơ
• Bài giảng Hóa học hữu cơ
• Keto enol equilibria
• Adol condensation
• In this workbook
• experiments are elaborated using small scale glassware and equipments from a Small Lab Kit
• developed at the Department of Chemistry
• Faculty of Science
• Chulalongkorn University in Thailand
• This Small Lab Kit was created as a result of the research project entitled “Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” sponsored by Thai Research Fund (RDG 3 07 2543)
• One of the outcomes of this project is the organic laboratory book entitled “Organic Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” written in Thai by professors from 7 universities in this project
• They compiled
• adjusted and tested the experiments taken from several traditional organic chemistry laboratory books using the prototype of Small Lab Kit
• Currently
• some selected experiments from this Thai organic chemistry laboratory text have further been modified
• rewritten and edited in English as appeared in this workbook
• Some experiments ar
• Ebook Organic chemistry
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