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

2. Carboxylic Acids (General)
carboxyl group
three ways to represent a carboxylic acid
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

7. 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

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

9. 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 !!!

10. 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)

11. What happens to Fischer Esterification ?
Nucleophilic Acyl Substitution !!!
Please take a look at eq on page 301
Protecting group
Tetrahedral intermediate

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