Essential Organic Chemistry Bruice • 3rd Edition •

Ch.1 - Remembering General Chemistry

Intro to Organic Chemistry Atomic Structure Wave Function Molecular Orbitals Sigma and Pi Bonds Octet Rule Bonding Preferences Formal Charges Skeletal Structure Lewis Structure Condensed Structural Formula Isomer Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch.2 - Acids and Bases

Organic Chemistry Reactions Reaction Mechanism Acids and Bases Give the conjugate acid for each compound below Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity Lewis Acids and Bases

Ch.3 - An Introduction to Organic Compounds

Degrees of Unsaturation Isomer Constitutional Isomers Functional Groups Carbonyl Amine Amide IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Alcohols Naming Ethers Naming Amines Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation Ring Strain Axial vs Equatorial Cis vs Trans Conformations Chair Flip Equatorial Preference Decalin

Ch. 4 - Isomers

Cis vs Trans Constitutional Isomers vs. Stereoisomers Chirality Test 1: Plane of Symmetry Test 2: Stereocenter Test R and S Configuration Enantiomers vs. Diastereomers Meso Compound Test 3: Disubstituted Cycloalkanes What is the Relationship Between Isomers? Achiral

Ch. 5 - Alkenes

Degrees of Unsaturation Naming Alkenes Gibbs Free Energy Energy Diagram Enthalpy Entropy

Ch. 6 - The Reactions of Alkenes and Alkynes

Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability Radical Stability Alkene Stability Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Hydrogenation Naming Alkenes Alkyne Hydrohalogenation Hydrogenation of Alkynes Alkyne Hydration Hydrogenation of Alkynes

Ch. 7 - Delocalized Electrons and Their Effect

Resonance Structures Diene Conjugation Chemistry Stability of Conjugated Intermediates Allylic Halogenation Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Diels-Alder Reaction Diels-Alder Forming Bridged Products Diels-Alder Retrosynthesis Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Electrophilic Aromatic Substitution Benzene Reactions

Ch. 8 - Substitution and Elimination Reactions of Alkyl Halides

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Solvents Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch. 9 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols

Alcohol Nomenclature Naming Epoxides Naming Thiols Dehydration Reaction Oxidizing and Reducing Agents Oxidizing Agent Ether Cleavage Epoxide Reactions Thiol Reactions

Ch. 10 - Determining the Structure of Organic Compounds

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

Ch. 11 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Naming Carboxylic Acids Acid Chloride Nomenclature Naming Anhydrides Naming Esters Naming Amides Naming Nitriles Carboxylic Acid Carboxylic Acid Derivatives Fischer Esterification (Simplified) Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride

Ch. 12 - Reactions of Aldehydes and Ketones

Naming Aldehydes Naming Ketones Nucleophilic Addition Preparation of Organometallics Grignard Reaction Cyanohydrin Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Imine vs Enamine Reductive Amination Conjugate Addition Ketone and Aldehyde Synthesis Reactions

Ch. 13 - Reactions at the Alpha-Carbon

Tautomerization Enolate Enolate Alkylation and Acylation Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen Condensation Decarboxylation Mechanism

Ch. 14 - Radicals

Radical Reaction Radical Stability Free Radical Halogenation Radical Selectivity

Ch. 15 - Synthetic Polymers

Free Radical Polymerization

Ch. 16 - The Organic Chemistry of Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Common Structures Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation Epimerization Monosaccharides - Aldose-Ketose Rearrangement Glycoside Disaccharide Polysaccharide

Ch. 17 - The Organic Chemistry of Amino Acids, Peptides, and Proteins

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