Chemistry 211 - Review Sheet for Exam #3

You should be familiar with the concepts listed below.Know reaction mechanisms for carboxylic acids and derivatives, as well as esters and amines.

Chapter 20: Carboxylic acids Carboxylic acid derivatives Acyl chlorides Acid anhydrides Esters Carboxamides Nomenclature Acid structure Nucleophilic substitution Acyl chloride preparation Thionyl chloride (SOCl2) Acid anhydride preparation Acid-catalyzed ester hydrolysis Basic hydrolysis of esters Saponification Ester reactions with ammonia and amines Amide preparation Lactams (cyclic amides) Nitriles preparation Hydrolysis of nitriles Approximate pKa values: NH4+/NH3 ~ 9 RNH3+/RNH2 ~ 10.5 HOH/OH- ~ 15.7 ROH/RO- ~ 16 NH3/NH2- ~ 36 RH/R- ~ 50-60

Chapter 21: Ester enolates β-keto esters (pKa ~ 11) Claisen condensation Intramolecular Claisen condensations Mixed Claisen condensation Ketone acylation with esters Ketone synthesis via β-keto esters Acetoacetic ester synthesis Malonic ester synthesis Barbiturates (reaction of malonic ester and urea, followed by alkylation) Michaels reaction General Review Information: Reaction mechanisms Transition states Grignard reaction Electrophiles Nucleophiles Substitution reactions Addition reactons Resonance structures Oxidation - reduction Lewis acids & bases Bronsted-Lowry acid Synthesis planning Retrosynthesis

Chapter 22: Amines Alkylamines & Aryl amines 1o, 2o, 3o, and 4o amines Amine nomenclature Structure and bonding Amine bond angles Physical properties Melting and boiling points Amine basicity (Table 22.1) pKa and pKb Tetraalkylammonium salts as phase-transfer catalysts Amine preparation Gabriel synthesis (phthalimide) of primary amines Hydrazine Amine preparation via reduction Reductive amination Reaction of amines with alkyl halides Electrophilic substitution in arylamines Protecting group nitrites and nitrous acid Nitrosation of alkylamines Nitrosamines from 2o amines Diazonium ion Nitrosation of arylamines Reactions of aryl diazonium ions Reductive deamination Azo coupling