Chemistry 211 - Review Sheet for Exam #2

You should be familiar with the concepts listed below. Know reaction mechanisms for reactions with aldehydes, ketones, carboxylic acids and carboxylic acid derivatives. Know nomenclature. Understand synthesis planning steps to make complex molecules from less complex ones.

Chapter 17: Aldehydes Ketones Nomenclature Carbonyl group Orbital hybridization Physical properties Preparation of aldehydes and ketones ozonolysis hydration of alkynes Friedel-Crafts acylation of aromatic compounds 1o alcohol oxidation 2o alcohol oxidation Aldehyde & ketone reactions Reduction to alcohols Addition of Grignard reagents Hydration of aldehydes & ketones Cyanohydrin formation Hemiacetals (C-O-C-OH) Acetals (C-O-C-O-C) Protecting groups (acetals) Reaction with primary amines (imines) Reaction with secondary amines (enamines) Oxidation of aldehydes Ketal & hemiketal Organometallic addition Protecting groups

Chapter 18: Keto - enol tautomerism α-halogenation & mechanism Enolization Enol (in acid) Enolate (in base) Stablized enols Haloform reaction Aldol condensation α,β-unsaturated aldehydes (ketones) Mixed aldol condensation Conjugate addition to α,β-unsaturated carbonyl compounds Michaels reaction General Review Information: Reaction mechanisms Transition states Grignard reaction Electrophiles Nucleophiles Substitution reactions Addition reactons Resonance structures Oxidation - reduction Lewis acids & bases Brønsted-Lowry acid Synthesis planning Retrosynthesis

Chapter 19: Carboxylic acids Nomenclature Structure and bonding Physical properties Carboxylic acid acidity inductive effective resonance effect Salts of carboxylic acids Esters Saponification Ionization Sources of carboxylic acids Acids Grignard reagents Nitriles: preparation of carboxylic acids Carboxylic acid reactions formation of acid chlorides LiAlH4 reduction to alcohols esterification with alcohols Mechanism of acid-catalyzed esterification Tetrahedral intermediate Lactones α-halogenation Decarboxylation