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Definitions and explanations for various terms related to carboxylic acids, including nomenclature, structure and bonding, physical properties, acidity, salts, preparation methods, and reactions. It covers topics such as carboxyl group hybridization, resonance forms, hydrogen bonding, acidity factors, and common reactions.
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Side-chain oxidation of alkylbenzenes The benzylic C must have at least one H Oxidation of 10 alcohols The carboxylic acids formed have the same number of C with the alcohols. Oxidation of aldehydes The formed carboxylic acids have the same number of C with the aldehydes. Ozonolysis of alkynes Useful if we start with symmetric alkynes Carboxylation of Grignard reagents The reaction converts an RX to a carboxylic acid with one more carbon than the starting halide. The halide could be 10, 20, 30 , aryl or vinyl halide, but cant contain OH, NH or SH groups. Preparation and hydrolysis of nitriles The reaction converts an RX to a carboxylic acid with one more carbon than the starting halide. The halide can only be methyl, 10 or 20 halides. 30, aryl or vinyl halides dont work. Preparation and hydrolysis of cyanohydrin TERM 8
Reaction with base Reduction with LiAlH4 Formation of acyl chlorides Esterification Mechanism of acid-catalyzed esterification (Fischer Esterification) Protonation of carbonyl group activates carbonyl carbon. Nucleophilic addition of alcohol to protonated carbonyl group forms tetrahedral intermediate. Elimination of water from tetrahedral intermediate restores carbonyl group. Intramolecular ester formation: Lactones Formed by intramolecular esterification in a hydroxy acid compound (contain a hydroxyl group and a carboxylic acid functional group) The reaction is most favorable if the resulting ring is 5 or 6-membered. Decarboxylation Simple carboxylic acids that contain only one CO2H group dont go thermal decarboxylation easily. But for diacids with the two CO2H groups separated by one other carbon or b-keto acids, thermal decarboxylation occurs readily. One carbonyl group assists the loss of CO2 from the CO2H group. The product is a carboxylic acid. The product of decarboxylation of diacids (R = OH) is acids; decarboxylation of b-keto acids (R = alkyl) results in ketones.