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![Page 1: Organic chemistry for medicine and biology students Chem 2311 Chapter 19 & 20 Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah Islamic.](https://reader036.fdocuments.us/reader036/viewer/2022062423/56649f335503460f94c4f177/html5/thumbnails/1.jpg)
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
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Diacids
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Physical Properties of carboxylic acids
Hydrogen bonding
Solubility in water
(lower acids)
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Acidity of carboxylic acids
pKa = -log Ka
As Ka increase or pKa decrease, the acidity increase
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Resonance and Inductive effect
Conversion of acids to salts
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Preparation of carboxylic acids
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Acids, hydroxy acids, amino acids, and unsaturated acids from cyanohydrines
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Reactions of carboxylic acids
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Hell-Volhard-Zelinsky Reaction
Treatment with bromine and a catalytic amount of phosphorus leads to the selective α-bromination of carboxylic acids.
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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.
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EstersNomenclature
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Examples
O
OMe H
OO
OPh
O
OEt
CH3 O
O
Cl
OEt
OH
CH3CH3 O
O
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Lactones (Cyclic Esters)
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Reactions of Esters with Grignard Reagent
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Formation of Amides (Ammonolysis of Esters)
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Reduction of EstersEsters can be reduced to primary alcohols
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The Cliasen Condensation
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Acid HalidesThey are prepared from the reaction of acids with thionyl chloride or
phosphorus halides
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Reactions of acid chloridesAcid chlorides react rapidly with most nucleophiles such as water,
alcohols and ammonia
Acyl halides have irritating odors. Benzoyl chlorid is a lachrymator
(tear gas)
CH3 Cl
O
CH3 OH
O
CH3 OR
O
CH3 NH2
O
H2O
EtOH
NH3
+
+
+
HCl
HCl
HCl
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Reaction with Grignard Reagent
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Preparation of mixed anhydrides
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• Mixed anhydrides CH3 O
OO
Ph
Acetic benzoic anhydride
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Nucleophilic substitution of anhydrides
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Amides
• Nomenclature
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• Properties of Amides
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Amide Resonance
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Reactions of Amides (Hydrolysis and Reduction)
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