Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah

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Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah Organic chemistry for medicine and biology students Chem 2311 Chapter 10 Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah Islamic University of Gaza

Diacids

Physical Properties of carboxylic acids Hydrogen bonding Solubility in water (lower acids)

Acidity of carboxylic acids pKa = -log Ka As Ka increase or pKa decrease, the acidity increase

Resonance and Inductive effect Conversion of acids to salts

Preparation of carboxylic acids

Reactions of carboxylic acids

Esters Nomenclature

Examples

Lactones (Cyclic Esters)

Formation of Amides (Ammonolysis of Esters)

Reduction of Esters Esters can be reduced to primary alcohols

Acid Halides They are prepared from the reaction of acids with thionyl chloride or phosphorus halides

Reactions of acid chlorides Acid chlorides react rapidly with most nucleophiles such as water, alcohols and ammonia Acyl halides have irritating odors. Benzoyl chlorid is a lachrymator (tear gas)

Preparation of mixed anhydrides

Mixed anhydrides

Nucleophilic substitution of anhydrides

Amides Nomenclature

Properties of Amides

Amide Resonance

Reactions of Amides (Hydrolysis and Reduction)