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  Bonds &  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 –H 2, HBr, Br 2 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 – H 2, HBr, Br 2 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: LiAlH 4 RMgBr – Reversible additions: alcohols => hemiacetal & acetal – Addition-Elimination: amines => imines

Chem 341 Review for Finals Reaction Types Reactions involving Enol Intermediates – Exchange of ketone  -hydrogens with D 2 O – 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 LiAlH 4

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 S N 2 Reaction –amine reaction with 1° halide S N 1 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