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Natural Products Nomenclature Acidity Preparation Reactions
Carboxylic Acids Natural Products Nomenclature Acidity Preparation Reactions
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Analgesics
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Fats and Fatty Acids
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Prostaglandins
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Penicillins from mold
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From Ergot Fungus
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Common Nomenclature
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I.U.P.A.C. Nomenclature
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Dicarboxylic Acids
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A Diacid
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Unusually High Melting and Boiling Points
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Boiling Points
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Acidity is due to Delocalization of the Charge in the Conjugate Base
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Alcohol vs. Acid
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e- Withdrawing Groups Enhance Acidity
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Benzoic acids
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Deprotonation
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Carboxylic Acid Preparations
Oxidation of 1o alcohols and aldehydes with Na2Cr2O7/H2SO4 KMnO4 oxidation of alkylbenzenes Grignard reaction with CO2 (Carboxylation) Hydrolysis of a carboxylic derivative: e.g. acid chloride, acid anhydride, ester, amide, nitrile
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Grignard Reaction with CO2
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Mechanism
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Hydrolysis of a Nitrile
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Reduction of Carboxylic Acids
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Carboxylic Acid Derivatives
Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution
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Reactivity of Acid Derivatives
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I.U.P.A.C. Nomenclature (uses carboxylic acid template)
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Acid Chlorides
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Acid Anhydrides
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Esters
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Amides
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Lactones (cyclic esters)
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Gamma Hydroxybutyrate
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All Acid Derivatives can be Hydrolyzed
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What are the 3 Hydrolysis Products?
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Draw the Hydrolysis Products
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Hydrolysis of Penicillin
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Aspartame
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Nucleophilic Acyl Substitution
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Nucleophilic Acyl Substitution
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Hydrolysis of an Acid Chloride
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Acid Chloride Preparation
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With Acid Chlorides, No Catalyst is Needed Anhydride Prep.
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Ester Preparation from an acid chloride
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Amide Preparation from an Acid Chloride
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Amide from Anhydride
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Fischer Esterification
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Flavors and Fragrances
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Intramolecular Fischer Esterification - GHB
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Lactam (cyclic amide) Formation
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b-Lactams as Antibiotics
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Acid Catalyzed “Olysis” Reactions
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Transesterification a Methanolysis
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Aspirin Synthesis
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Basic Hydrolysis Saponification
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Basic Hydrolysis of an Amide
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Mechanism
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Reduction of Esters with LiAlH4
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DIBAH Diisobutyl Aluminum Hydride
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