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Chem 341 Review for Finals Structure Determination • NMR –Chemical shifts, splitting patterns, integrations • IR –ROH, C=O • Formula => # of Rings + Pi-Bonds Chem 341 Review for Finals Structure and Bonding • s- Bonds & p-Bonds • Resonance Structures • Aromaticity –Heterocycles • Pyramidal Amines & Flat Amides • Cyclohexane Chem 341 Review for Finals Physical Properties Boiling Points and Water Solubility • Hydrocarbons – weak forces, van der Waals Attraction • Ethers, Ketones, Esters, Halides –medium strength attraction: dipoles • Alcohols, Acids, Amides – strong attraction: hydrogen bonds Chem 341 Review for Finals Isomers • Structural Isomers • Stereoisomers –Enantiomers (Chirality; R/S nomenclature) –Diastereomers (meso isomers) • epimers and anomers • tautomers: ketones and enols Chem 341 Review for Finals Classes of Compounds • Synthetic Polymers – Polyesters, Polyamides, – Radical Polymerization of alkenes • Lipids and Detergents –Fats, Waxes, Soaps, Detergents, miceles, Phospholipid bi-layers • Carbohydrates – hexose, pentose, furanose, pyranose, aldose, ketose, di- and polysaccharides, anomeric center Chem 341 Review for Finals Classes of Compounds • Amino Acids – acidic, basic, neutral – isoelectric point – peptides and proteins • Nucleotides and Nucleic Acids – purine and pyrimidine bases – ribose and deoxyribose – phosphate links between sugars – hydrogen bonding of base pairs Chem 341 Review for Finals Acidity • pKa and pH relationships –Alcohols - phenols - carboxylic acids –Alkyl amines - aryl amines • Amino Acids –Isoelectric point Chem 341 Review for Finals Reaction Types • Reaction Energy Diagrams • Additions to Alkenes –H2, HBr, Br2 • Electrophilic Aromatic Substitution (ortho/para vs meta directing groups) - Nitration, bromination, alkylation, sulfonation, alkylation, acylation Chem 341 Review for Finals Reaction Types • Reaction Energy Diagrams • Additions to Alkenes – H2, HBr, Br2 • Reactions of Organic Halides - Sn1, Sn2, E2 - Carbocation stabilities Chem 341 Review for Finals Reaction Types • Reactions of Alcohols –Dehydration, conversion to alkyl halides –Oxidation of alcohols to aldehydes or acids –Concept of oxidizing and reducing agents • Ether Synthesis • Epoxide ring opening Chem 341 Review for Finals Reaction Types • RMgBr (Grignard Reagents) –Preparation from alkyl halides –Reactions with aldehydes, ketones, and esters • Nucleophilic Addition to Ketones – Irreversible additions: LiAlH4 RMgBr – Reversible additions: alcohols => hemiacetal & acetal – Addition-Elimination: amines => imines Chem 341 Review for Finals Reaction Types • Reactions involving Enol Intermediates – Exchange of ketone a-hydrogens with D2O – Aldol condensation: addition of enolate anion to an aldehyde carbonyl carbon • Carboxylic acid derivatives – Relative reactivity: Acid halides > Anhydrides > Esters > Amides > – Synthesis and Hydrolysis of Esters and Amides – Reactions of Esters with RMgBr and LiAlH4 Chem 341 Review for Finals Reaction Types • Reactions of Amines • Carbohydrates – Reactions interconverting aldehydes and cyclic hemiacetals, the anomeric center Chem 341 Review for Finals Key Reactions Mechanisms • Electrophilic Addition to Alkenes – HBr Addition to 1-hexene • SN2 Reaction –amine reaction with 1° halide • SN1 Reaction –water reaction with 3° halide Chem 341 Review for Finals Key Reactions Mechanisms • E2 Elimination –base reaction with a 2° halide to give alkene • Electrophilic Aromatic Substitution – nitration of benzene • Hemiacetal Formation –Acid catalyzed reaction of alcohols with aldehydes to give hemiacetal (sugars) Chem 341 Review for Finals Key Reactions Mechanisms • Nucleophilic addition to Carbonyl Groups –Base catalyzed hydrolysis of esters • Acid Catalyzed Esterification –Synthesis of esters from acids and alcohols • Aldol Condensation – enolate anion addition to carbonyl carbon