Chem 341 Review for Finals Structure Determination

1. Chem 341 Review for FinalsStructure Determination NMR Chemical shifts, splitting patterns, integrations IR ROH, C=O Formula => # of Rings + Pi-Bonds

2. Chem 341 Review for FinalsStructure and Bonding s- Bonds & p-Bonds Resonance Structures Aromaticity Heterocycles Pyramidal Amines & Flat Amides Cyclohexane

3. Chem 341 Review for FinalsPhysical PropertiesBoiling 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

4. Chem 341 Review for FinalsIsomers Structural Isomers Stereoisomers Enantiomers (Chirality; R/S nomenclature) Diastereomers (meso isomers) epimers and anomers tautomers: ketones and enols

5. Chem 341 Review for FinalsClasses 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

6. Chem 341 Review for FinalsClasses 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

7. Chem 341 Review for FinalsAcidity pKa and pH relationships Alcohols - phenols - carboxylic acids Alkyl amines - aryl amines Amino Acids Isoelectric point

8. Chem 341 Review for FinalsReaction 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

9. Chem 341 Review for FinalsReaction Types Reaction Energy Diagrams Additions to Alkenes H2, HBr, Br2 Reactions of Organic Halides Sn1, Sn2, E2 Carbocation stabilities

10. Chem 341 Review for FinalsReaction 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

11. Chem 341 Review for FinalsReaction 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

12. Chem 341 Review for FinalsReaction 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

13. Chem 341 Review for FinalsReaction Types Reactions of Amines Carbohydrates Reactions interconverting aldehydes and cyclic hemiacetals, the anomeric center

14. Chem 341 Review for FinalsKey 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

15. Chem 341 Review for FinalsKey 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)

16. Chem 341 Review for FinalsKey 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