Table of contents
- 1. A Review of General Chemistry(576)
- Summary(19)
- Intro to Organic Chemistry(20)
- Atomic Structure(27)
- Wave Function(18)
- Molecular Orbitals(21)
- Sigma and Pi Bonds(21)
- Octet Rule(20)
- Bonding Preferences(24)
- Formal Charges(28)
- Skeletal Structure(20)
- Lewis Structure(39)
- Condensed Structural Formula(35)
- Degrees of Unsaturation(32)
- Constitutional Isomers(19)
- Resonance Structures(94)
- Hybridization(36)
- Molecular Geometry(32)
- Electronegativity(71)
- 2. Molecular Representations(99)
- 3. Acids and Bases(465)
- 4. Alkanes and Cycloalkanes(588)
- IUPAC Naming(32)
- Alkyl Groups(23)
- Naming Cycloalkanes(20)
- Naming Bicyclic Compounds(20)
- Naming Alkyl Halides(26)
- Naming Alkenes(68)
- Naming Alcohols(22)
- Naming Amines(23)
- Cis vs Trans(85)
- Conformational Isomers(20)
- Newman Projections(20)
- Drawing Newman Projections(31)
- Barrier To Rotation(21)
- Ring Strain(21)
- Axial vs Equatorial(20)
- Cis vs Trans Conformations(20)
- Equatorial Preference(31)
- Chair Flip(20)
- Calculating Energy Difference Between Chair Conformations(19)
- A-Values(26)
- Decalin(20)
- 5. Chirality(433)
- Constitutional Isomers vs. Stereoisomers(65)
- Chirality(21)
- Test 1:Plane of Symmetry(20)
- Test 2:Stereocenter Test(20)
- R and S Configuration(71)
- Enantiomers vs. Diastereomers(19)
- Atropisomers(20)
- Meso Compound(20)
- Test 3:Disubstituted Cycloalkanes(20)
- What is the Relationship Between Isomers?(25)
- Fischer Projection(23)
- R and S of Fischer Projections(23)
- Optical Activity(21)
- Enantiomeric Excess(24)
- Calculations with Enantiomeric Percentages(21)
- Non-Carbon Chiral Centers(20)
- 6. Thermodynamics and Kinetics(242)
- 7. Substitution Reactions(283)
- 8. Elimination Reactions(319)
- 9. Alkenes and Alkynes(311)
- 10. Addition Reactions(796)
- Addition Reaction(20)
- Markovnikov(20)
- Hydrohalogenation(72)
- Acid-Catalyzed Hydration(57)
- Oxymercuration(30)
- Hydroboration(63)
- Hydrogenation(39)
- Halogenation(46)
- Halohydrin(49)
- Carbene(27)
- Epoxidation(33)
- Epoxide Reactions(61)
- Dihydroxylation(48)
- Ozonolysis(70)
- Ozonolysis Full Mechanism(20)
- Oxidative Cleavage(20)
- Alkyne Oxidative Cleavage(20)
- Alkyne Hydrohalogenation(21)
- Alkyne Halogenation(36)
- Alkyne Hydration(22)
- Alkyne Hydroboration(22)
- 11. Radical Reactions(313)
- 12. Alcohols, Ethers, Epoxides and Thiols(489)
- Alcohol Nomenclature(23)
- Naming Ethers(30)
- Naming Epoxides(20)
- Naming Thiols(21)
- Alcohol Synthesis(21)
- Leaving Group Conversions - Using HX(24)
- Leaving Group Conversions - SOCl2 and PBr3(19)
- Leaving Group Conversions - Sulfonyl Chlorides(29)
- Leaving Group Conversions Summary(20)
- Williamson Ether Synthesis(50)
- Making Ethers - Alkoxymercuration(20)
- Making Ethers - Alcohol Condensation(20)
- Making Ethers - Acid-Catalyzed Alkoxylation(20)
- Making Ethers - Cumulative Practice(20)
- Ether Cleavage(29)
- Alcohol Protecting Groups(20)
- t-Butyl Ether Protecting Groups(20)
- Silyl Ether Protecting Groups(20)
- Sharpless Epoxidation(23)
- Thiol Reactions(20)
- Sulfide Oxidation(20)
- 13. Alcohols and Carbonyl Compounds(452)
- 14. Synthetic Techniques(142)
- 15. Analytical Techniques:IR, NMR, Mass Spect(531)
- Purpose of Analytical Techniques(19)
- Infrared Spectroscopy(24)
- Infrared Spectroscopy Table(32)
- IR Spect:Drawing Spectra(20)
- IR Spect:Extra Practice(9)
- NMR Spectroscopy(21)
- 1H NMR:Number of Signals(27)
- 1H NMR:Q-Test(20)
- 1H NMR:E/Z Diastereoisomerism(20)
- H NMR Table(25)
- 1H NMR:Spin-Splitting (N + 1) Rule(21)
- 1H NMR:Spin-Splitting Simple Tree Diagrams(26)
- 1H NMR:Spin-Splitting Complex Tree Diagrams(20)
- 1H NMR:Spin-Splitting Patterns(23)
- NMR Integration(20)
- NMR Practice(52)
- Carbon NMR(49)
- Structure Determination without Mass Spect(22)
- Mass Spectrometry(20)
- Mass Spect:Fragmentation(41)
- Mass Spect:Isotopes(20)
- 16. Conjugated Systems(593)
- Conjugation Chemistry(46)
- Stability of Conjugated Intermediates(21)
- Allylic Halogenation(20)
- Reactions at the Allylic Position(20)
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)(31)
- Diels-Alder Reaction(46)
- Diels-Alder Forming Bridged Products(22)
- Diels-Alder Retrosynthesis(20)
- Molecular Orbital Theory(20)
- Drawing Atomic Orbitals(20)
- Drawing Molecular Orbitals(20)
- HOMO LUMO(20)
- Orbital Diagram:3-atoms- Allylic Ions(20)
- Orbital Diagram:4-atoms- 1,3-butadiene(20)
- Orbital Diagram:5-atoms- Allylic Ions(20)
- Orbital Diagram:6-atoms- 1,3,5-hexatriene(20)
- Orbital Diagram:Excited States(20)
- Pericyclic Reaction(21)
- Thermal Cycloaddition Reactions(20)
- Photochemical Cycloaddition Reactions(21)
- Thermal Electrocyclic Reactions(20)
- Photochemical Electrocyclic Reactions(21)
- Cumulative Electrocyclic Problems(20)
- Sigmatropic Rearrangement(24)
- Cope Rearrangement(19)
- Claisen Rearrangement(21)
- 17. Ultraviolet Spectroscopy(70)
- 18. Aromaticity(243)
- 19. Reactions of Aromatics: EAS and Beyond(597)
- Electrophilic Aromatic Substitution(24)
- Benzene Reactions(20)
- EAS:Halogenation Mechanism(20)
- EAS:Nitration Mechanism(20)
- EAS:Friedel-Crafts Alkylation Mechanism(22)
- EAS:Friedel-Crafts Acylation Mechanism(21)
- EAS:Any Carbocation Mechanism(20)
- Electron Withdrawing Groups(75)
- EAS:Ortho vs. Para Positions(19)
- Acylation of Aniline(19)
- Limitations of Friedel-Crafts Alkyation(20)
- Advantages of Friedel-Crafts Acylation(20)
- Blocking Groups - Sulfonic Acid(19)
- EAS:Synergistic and Competitive Groups(20)
- Side-Chain Halogenation(20)
- Side-Chain Oxidation(20)
- Reactions at Benzylic Positions(20)
- Birch Reduction(20)
- EAS:Sequence Groups(20)
- EAS:Retrosynthesis(58)
- Diazo Replacement Reactions(20)
- Diazo Sequence Groups(20)
- Diazo Retrosynthesis(20)
- Nucleophilic Aromatic Substitution(20)
- Benzyne(20)
- 20. Phenols(78)
- 21. Aldehydes and Ketones: Nucleophilic Addition(567)
- Naming Aldehydes(20)
- Naming Ketones(20)
- Oxidizing and Reducing Agents(21)
- Oxidation of Alcohols(20)
- Ozonolysis(19)
- DIBAL(20)
- Alkyne Hydration(19)
- Nucleophilic Addition(25)
- Cyanohydrin(20)
- Organometallics on Ketones(21)
- Overview of Nucleophilic Addition of Solvents(20)
- Hydrates(20)
- Hemiacetal(20)
- Acetal(21)
- Acetal Protecting Group(21)
- Thioacetal(18)
- Imine vs Enamine(111)
- Addition of Amine Derivatives(19)
- Wolff Kishner Reduction(20)
- Baeyer-Villiger Oxidation(21)
- Acid Chloride to Ketone(20)
- Nitrile to Ketone(21)
- Wittig Reaction(20)
- Ketone and Aldehyde Synthesis Reactions(10)
- 22. Carboxylic Acid Derivatives: NAS(468)
- Carboxylic Acid Derivatives(22)
- Naming Carboxylic Acids(21)
- Diacid Nomenclature(20)
- Naming Esters(20)
- Naming Nitriles(20)
- Acid Chloride Nomenclature(20)
- Naming Anhydrides(20)
- Naming Amides(20)
- Nucleophilic Acyl Substitution(112)
- Carboxylic Acid to Acid Chloride(20)
- Fischer Esterification(20)
- Acid-Catalyzed Ester Hydrolysis(35)
- Saponification(19)
- Transesterification(21)
- Lactones, Lactams and Cyclization Reactions(17)
- Carboxylation(20)
- Decarboxylation Mechanism(21)
- Review of Nitriles(20)
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides(99)
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon(266)
- Tautomerization(21)
- Tautomers of Dicarbonyl Compounds(21)
- Enolate(22)
- Acid-Catalyzed Alpha-Halogentation(20)
- Base-Catalyzed Alpha-Halogentation(19)
- Haloform Reaction(20)
- Hell-Volhard-Zelinski Reaction(20)
- Overview of Alpha-Alkylations and Acylations(20)
- Enolate Alkylation and Acylation(19)
- Enamine Alkylation and Acylation(21)
- Beta-Dicarbonyl Synthesis Pathway(20)
- Acetoacetic Ester Synthesis(22)
- Malonic Ester Synthesis(21)
- 25. Condensation Chemistry(263)
- 26. Amines(218)
- 27. Heterocycles(152)
- Nomenclature of Heterocycles(19)
- Acid-Base Properties of Nitrogen Heterocycles(20)
- Reactions of Pyrrole, Furan, and Thiophene(20)
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes(19)
- Addition Reactions of Furan(18)
- EAS Reactions of Pyridine(18)
- SNAr Reactions of Pyridine(18)
- Side-Chain Reactions of Substituted Pyridines(20)
- 28. Carbohydrates(525)
- Monosaccharide(20)
- Monosaccharides - D and L Isomerism(21)
- Monosaccharides - Drawing Fischer Projections(21)
- Monosaccharides - Common Structures(20)
- Monosaccharides - Forming Cyclic Hemiacetals(23)
- Monosaccharides - Cyclization(20)
- Monosaccharides - Haworth Projections(21)
- Mutarotation(20)
- Epimerization(22)
- Monosaccharides - Aldose-Ketose Rearrangement(22)
- Monosaccharides - Alkylation(21)
- Monosaccharides - Acylation(21)
- Glycoside(22)
- Monosaccharides - N-Glycosides(20)
- Monosaccharides - Reduction (Alditols)(20)
- Monosaccharides - Weak Oxidation (Aldonic Acid)(21)
- Reducing Sugars(23)
- Monosaccharides - Strong Oxidation (Aldaric Acid)(20)
- Monosaccharides - Oxidative Cleavage(20)
- Monosaccharides - Osazones(19)
- Monosaccharides - Kiliani-Fischer(22)
- Monosaccharides - Wohl Degradation(23)
- Monosaccharides - Ruff Degradation(20)
- Disaccharide(22)
- Polysaccharide(21)
- 29. Amino Acids(314)
- Proteins and Amino Acids(48)
- L and D Amino Acids(22)
- Polar Amino Acids(20)
- Amino Acid Chart(20)
- Acid-Base Properties of Amino Acids(25)
- Isoelectric Point(20)
- Amino Acid Synthesis: HVZ Method(20)
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis(20)
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis(20)
- Synthesis of Amino Acids: Strecker Synthesis(20)
- Reactions of Amino Acids: Esterification(19)
- Reactions of Amino Acids: Acylation(19)
- Reactions of Amino Acids: Hydrogenolysis(21)
- Reactions of Amino Acids: Ninhydrin Test(20)
- 30. Peptides and Proteins(239)
- Peptides(20)
- Primary Protein Structure(20)
- Secondary Protein Structure(20)
- Tertiary Protein Structure(20)
- Disulfide Bonds(20)
- Quaternary Protein Structure(19)
- Summary of Protein Structure(20)
- Intro to Peptide Sequencing(20)
- Peptide Sequencing: Partial Hydrolysis(20)
- Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide(20)
- Peptide Sequencing: Edman Degradation(20)
- Merrifield Solid-Phase Peptide Synthesis(20)
- 31. Catalysis in Organic Reactions(158)
- 32. Lipids (194)
- 33. The Organic Chemistry of Metabolic Pathways(272)
- Intro to Metabolism(19)
- ATP and Energy(19)
- Intro to Coenzymes(19)
- Coenzymes in Metabolism(20)
- Energy Production in Biochemical Pathways(20)
- Intro to Glycolysis(19)
- Catabolism of Carbohydrates: Glycolysis(20)
- Glycolysis Summary(20)
- Pyruvate Oxidation (Simplified)(20)
- Anaerobic Respiration(18)
- Catabolism of Fats: Glycerol Metabolism(20)
- Intro to Citric Acid Cycle(20)
- Structures of the Citric Acid Cycle(19)
- The Citric Acid Cycle(19)
- 34. Nucleic Acids(138)
- 35. Transition Metals(337)
- Electron Configuration of Elements(20)
- Coordination Complexes(20)
- Ligands(19)
- Electron Counting(20)
- The 18 and 16 Electron Rule(20)
- Cross-Coupling General Reactions(20)
- Heck Reaction(20)
- Stille Reaction(20)
- Suzuki Reaction(20)
- Sonogashira Coupling Reaction(20)
- Fukuyama Coupling Reaction(20)
- Kumada Coupling Reaction(20)
- Negishi Coupling Reaction(20)
- Buchwald-Hartwig Amination Reaction(20)
- Eglinton Reaction(19)
- Catalytic Allylic Alkylation(20)
- Alkene Metathesis(19)
- 36. Synthetic Polymers(251)
- Introduction to Polymers(19)
- Chain-Growth Polymers(20)
- Radical Polymerization(20)
- Cationic Polymerization(17)
- Anionic Polymerization(20)
- Polymer Stereochemistry(20)
- Ziegler-Natta Polymerization(19)
- Copolymers(20)
- Step-Growth Polymers(20)
- Step-Growth Polymers: Urethane(17)
- Step-Growth Polymers: Polyurethane Mechanism(19)
- Step-Growth Polymers: Epoxy Resin(20)
- Polymers Structure and Properties(20)
10. Addition Reactions
Halohydrin
10. Addition Reactions
Halohydrin: Videos & Practice Problems
12 of 49
Problem 12
Determine the reagents needed for (4R,5S)-1-ethyl-4,5-dimethylcyclohexene to form the given product.
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