Organic Chemistry: A Short Course Hart • 13th Edition • 9781111425562

Ch. 1 - Bonding and Isomerism

Intro to Organic Chemistry Atomic Structure Octet Rule Bonding Preferences Sigma and Pi Bonds Lewis Structure Electronegativity Constitutional Isomers Skeletal Structure Condensed Structural Formula Formal Charges Resonance Structures Hybridization Functional Groups Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch. 2 - Alkanes and Cycloalkanes; Conformational and Geometric Isomerism

IUPAC Naming Alkyl Groups Naming Alkyl Halides Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Intermolecular Forces How To Determine Solubility Conformational Isomers Newman Projections Drawing Newman Projections Naming Cycloalkanes Axial vs Equatorial Equatorial Preference Chair Flip Cis vs Trans Conformations Free Radical Halogenation

Ch. 3 - Alkenes and Alkynes

Naming Alkenes Cis vs Trans Halogenation Acid-Catalyzed Hydration Hydrohalogenation Markovnikov Addition Reaction Carbocation Stability Equilibrium Constant Energy Diagram Gibbs Free Energy Hydroboration Hydrogenation Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Diels-Alder Reaction Free Radical Polymerization Dihydroxylation Ozonolysis Epoxidation Alkyne Halogenation Hydrogenation of Alkynes Alkyne Hydrohalogenation Alkyne Hydration Acetylide

Ch. 4 - Aromatic Compounds

Aromaticity Benzene Reactions Naming Benzene Rings Electrophilic Aromatic Substitution EAS: Halogenation Mechanism EAS: Nitration Mechanism EAS: Friedel-Crafts Alkylation Mechanism EAS: Friedel-Crafts Acylation Mechanism EAS: Any Carbocation Mechanism Electron Withdrawing Groups EAS: Ortho vs. Para Positions

Ch. 5 - Stereoisomerism

Constitutional Isomers vs. Stereoisomers Chirality Test 1: Plane of Symmetry Test 2: Stereocenter Test R and S Configuration Optical Activity Fischer Projection R and S of Fischer Projections Enantiomers vs. Diastereomers Meso Compound What is the Relationship Between Isomers? Racemic Mixture Achiral

Ch. 6 - Organic Halogen Compounds; Substitution and Elimination Reactions

Alkyl Halide Nucleophilic Substitution SN2 Reaction SN1 Reaction Substitution Comparison Dehydrohalogenation E2 Mechanism E2 - Cumulative Practice E1 Reaction SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch. 7 - Alcohols, Phenols, and Thiols

Hydroxyl Group Naming Alcohols Alcohol Nomenclature Phenol Acidity Dehydration Reaction Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Oxidation of Alcohols Naming Thiols Thiol Reactions

Ch. 8 - Ethers and Epoxides

Naming Ethers Preparation of Organometallics Making Ethers - Alcohol Condensation Making Ethers - Acid-Catalyzed Alkoxylation Williamson Ether Synthesis Ether Cleavage Epoxidation Epoxide Reactions

Ch. 9 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols Nucleophilic Addition Overview of Nucleophilic Addition of Solvents Hemiacetal Acetal Hydrates Organometallics on Ketones Cyanohydrin Addition of Amine Derivatives DIBAL Acetal and Hemiacetal Tautomerization Enolate Aldol Condensation Crossed Aldol Condensation

Ch. 10 - Carboxylic Acids and Their Derivatives

Carboxylic Acid Naming Carboxylic Acids Diacid Nomenclature Side-Chain Oxidation Carboxylation Carboxylic Acid Derivatives Naming Esters Fischer Esterification (Simplified) Fischer Esterification Nucleophilic Acyl Substitution Lactones, Lactams and Cyclization Reactions Acid-Catalyzed Ester Hydrolysis Saponification Ester Naming Nitriles Acid Chloride Nomenclature Naming Anhydrides Naming Amides Carboxylic Acid to Acid Chloride Transesterification Claisen Condensation

Ch. 11 - Amines and Related Nitrogen Compounds

Naming Amines Amine Alkylation Amines by Reduction Reductive Amination Diazo Replacement Reactions Diazo Sequence Groups

Ch. 12 - Spectroscopy and Structure Determination

Purpose of Analytical Techniques NMR Spectroscopy 1H NMR: Number of Signals H NMR Table NMR Integration 1H NMR: Spin-Splitting (N + 1) Rule 1H NMR: Spin-Splitting Patterns NMR Practice Carbon NMR Structure Determination without Mass Spect Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Extra Practice Mass Spectrometry Mass Spect: Fragmentation

Ch. 13 - Heterocyclic Compounds

Aromatic Heterocycles Basicity of Aromatic Heterocycles Nucleophilic Aromatic Substitution

Ch. 16 - Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Drawing Fischer Projections Monosaccharides - Common Structures Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation Glycoside Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Disaccharide Polysaccharide

Ch. 17 - Amino Acids, Peptides, and Proteins

Proteins and Amino Acids Polar Amino Acids Amino Acid Chart L and D Amino Acids Acid-Base Properties of Amino Acids Isoelectric Point Peptide Bond