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Explore the physical properties, reactions, and preparation methods of carboxylic acids and their derivatives in this comprehensive guide by Prof. Dr. Adel M. Awadallah from the Islamic University of Gaza. Understand concepts like acidity, resonance, and the Hell-Volhard-Zelinsky Reaction.
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Organic chemistry for medicine and biology students Chem 2311 Chapter 19 & 20 Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah Islamic University of Gaza
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
Acids, hydroxy acids, amino acids, and unsaturated acids from cyanohydrines
Hell-Volhard-Zelinsky Reaction Treatment with bromine and a catalytic amount of phosphorus leads to the selective α-bromination of carboxylic acids.
Mechanism of the Hell-Volhard-Zelinsky ReactionPhosphorus reacts with bromine to give phosphorus tribromide, and in the first step this converts the carboxylic acid into an acyl bromide.
Esters Nomenclature
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)