Download Reactions for Exam 3: Formation and Derivatives of Carboxylic Acids and Nitriles - Prof. S and more Exams Organic Chemistry in PDF only on Docsity! List of Reactions for Exam 3 (CH232, summer 2007) * = mechanism covered chapter 20 - carboxylic acids and nitriles carboxylic acid formation via KMnO4 oxidation of alkenes benzoic acid formation via KMnO4 oxidation of alkylbenzenes * carboxylic acid formation via Jones oxidation of 1˚ alcohols * carboxylic acid formation via hydrolysis of nitriles (coupled with KCN rxn with RX = homologation rxn) * carboxylic acid formation via Grignard reagent carboxylation (rxn with CO2) reduction of carboxylic acids to alcohols with LiAlH4 (or with BH3/THF) * alkylation of cyanide anion by RX to make nitriles (SN2 rxn) * NH2-amide dehydration with SOCl2 * nitrile hydrolysis to make carboxylic acids * nitrile reduction by LiAlH4 to make 1˚ amines * nitrile reaction with Grignard reagents to give ketones chapter 21 - carboxylic acid derivatives and nucleophilic acyl substitution (NAS) * carboxylic acid conversion to acid chloride with SOCl2 * carboxylic acid conversion to esters (by carboxylate alkylation, diazomethane rxn, or Fischer esterification) * carboxylic acid conversion to amides using amine + DCC * acid chloride rxn with H2O (hydrolysis) to make acids * acid chloride rxn with ROH (alcoholysis) to make esters * acid chloride rxn with NH3, RNH2, or R2NH (aminolysis) to make acids * acid chloride reduction by LiAlH4 to make 1˚ ROH's * acid chloride rxn with Grignard reagents (RMgX) to make 3˚ ROH's acid chloride rxn with Gilman reagents (R2CuLi) to make ketones * anhydride NAS reactions (hydrolysis, alcoholysis, and aminolysis) to make acids, esters, and amides, respectively anhydride reduction by LiAlH4 to make 1˚ ROH's * ester rxn with H2O (hydrolysis) to make acids (acid or base catalyzed) * ester rxn with ROH (alcoholysis) to make another ester (acid or base catalyzed) - transesterification * ester rxn with ammonia or amines (aminolysis) to make amides * ester reduction by LiAlH4 to make 1˚ ROH's * ester reduction by DIBAH to make aldehydes * ester reaction with Grignard reagents (RMgX twice) to make 3˚ ROH's * amide rxn with H2O (hydrolysis) to give acids (acid or base catalyzed and heat needed) * amide reduction by LiAlH4 to make amines * NH2-amide dehydration by SOCl2 to make nitriles (as also covered in ch 21) chapter 22 - carbonyl alpha-substitution reactions (enolate chemistry I) * keto-enol tautomerization of aldehydes and ketones * alpha-halogenation of aldehydes and ketones * Hell-Volhard-Zelinskii reaction - alpha-bromination of carboxylic acids * enolate anion formation from aldehydes, ketones, and esters (also α-deprotonation of nitriles) * enolate anion halogenation * enolate anion selenation / oxidation / elimination to make α,β-unsaturated aldehydes, ketones, or esters * enolate anion alkylation * thermal decarboxylation (loss of CO2) of 1,3-diacids or 3-keto-acids * malonic ester synthesis of substituted acetic acids * acetoacetic ester synthesis of substituted acetones
