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Organic Chemistry Chapter 10 Part I

Organic Chemistry Chapter 10 Part I. Carboxylic Acids and Their Derivatives (Ester). Nanoplasmonic Research Group. Carboxylic Acids (General). three ways to represent a carboxylic acid. carboxyl group. acid derivatives. Organic Acids characterized the presence of a carboxylic group

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Organic Chemistry Chapter 10 Part I

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  1. Organic ChemistryChapter 10Part I Carboxylic Acids and Their Derivatives (Ester) Nanoplasmonic Research Group

  2. Carboxylic Acids (General) three ways to represent a carboxylic acid carboxyl group acid derivatives • Organic Acids characterized the presence of a carboxylic group • Bronsted-Lowry acids: Proton donors • Salts or Anions: Carboxylates

  3. Nomenclature • In IUPAC nomenclature: carboxylic acids have an -oic acid suffix • In common nomenclature, the suffix is usually -ic acid

  4. Physical Properties of Carboxylic Acids • Polar and form hydrogen bonds with each other • At high T, in vapor phase, carboxylic acids usually exist as dimeric pairs • Water solubility: Chain-length dependent

  5. Acidity of Carboxylic Acids • The acidity can be explained by either the stability of the acids or the stability of the conjugate base using inductive effect or resonance effect • The stability of the acids: Inductive effect • The stability of the conjugate base: Both

  6. Synthesis of Carboxylic Acids • Oxidation of Primary Alcohols and Aldehydes • Hydrolysis of Nitriles, Esters, or Amides with The Addition of Acid or Base • Roles of Acid or Base !!!!!! (page 298, 10.15) • Reaction of Grignard Reagents with Carbon Dioxide

  7. Carboxylic Acids Derivatives(Ester) • The R part of the -OR groups is named first , followed by the name of the acid, with the -icending changed to -ate • Ocurrence: the flavor and fragrance of many fruits and flowers • Hydrogen bond acceptor: Volatile than carboxylic acids • Cyclic ester: Lactone

  8. How to Prepare Ester ??- Fischer Esterification - • Refluxing a carboxylic acid in an alcohol, which acts as both solvent and reactant • Since the reaction is an equilibrium, how to push the equilibrium to the right ???? • le Chatelier’s principle !!!

  9. How to Push the equilibrium to the right ?- Fischer Esterification - • Using the alcohol as a solvent (in large excess) • Using Sulfuric Acid: It acts as an acid catalyst and as a dehydrating agent • Distillation (boiling point)

  10. What happens to Fischer Esterification ? • NucleophilicAcyl Substitution !!! • Please take a look at eq. 10.19 on page 301 • Protecting group • Tetrahedral intermediate

  11. Reactions of Esters • Saponification, Reduction,Ammonolysis, and Reaction with Grignard Reagent

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