Textbook Question
Describe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:
a.
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- 1. A Review of General Chemistry6h 54m
- Orgo 1: Pre-Course Review25m
- What is Organic Chemistry?10m
- Atomic Structure24m
- Wave Function9m
- Molecular Orbitals25m
- Sigma and Pi Bonds18m
- Octet Rule25m
- Bonding Preferences21m
- Formal Charges11m
- Skeletal Structure19m
- Lewis Structure20m
- Condensed Structural Formula22m
- Index of Hydrogen Deficiency (Structural)28m
- Constitutional Isomers21m
- Resonance Structures1h 0m
- Hybridization23m
- Molecular Geometry18m
- Electronegativity25m
- 2. Molecular Representations2h 3m
- 3. Acids and Bases4h 15m
- 4. Alkanes and Cycloalkanes5h 13m
- Alkane Nomenclature50m
- Alkyl Groups21m
- Naming Cycloalkanes10m
- Naming Bicyclic Compounds10m
- Naming Alkyl Halides7m
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- Naming Alcohols14m
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- Cis vs Trans21m
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- Newman Projections14m
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- Barrier To Rotation9m
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- Chair Flip9m
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- A-Values17m
- Decalin12m
- 5. Chirality5h 36m
- Types of Isomers21m
- Chirality12m
- Chirality Test 1 - Internal Line of Symmetry16m
- Chirality Test 2 - Stereocenters34m
- Cahn-Ingold-Prelog Nomenclature1h 2m
- Types of Stereoisomers18m
- Atropisomers24m
- Meso Compounds18m
- Chirality Test 3 - Disubstituted Cycloalkanes Shortcuts30m
- Isometric Relationships22m
- Fischer Projection10m
- Fischer Configurations11m
- Optical Activity5m
- Enantiomeric Excess25m
- Calculations with Enantiomeric Percentages13m
- Non-Carbon Chiral Centers8m
- 6. Thermodynamics and Kinetics1h 40m
- 7. Substitution Reactions2h 13m
- 8. Elimination Reactions2h 53m
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- 10. Addition Reactions4h 29m
- General Mechanism – Addition Reaction9m
- Markovnikov's Rule7m
- Hydrohalogenation8m
- Acid-Catalyzed Hydration20m
- Oxymercuration-Reduction23m
- Hydroboration-Oxidation34m
- Catalytic Hydrogenation and Wilkinson's Catalyst10m
- Halogenation14m
- Halohydrin Formation21m
- Cyclopropanation14m
- Epoxidation8m
- Epoxide Ring Opening15m
- Syn Vicinal Dihydroxylation14m
- Weak Oxidative Cleavage11m
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- Oxidative Cleavage3m
- Alkyne Oxidative Cleavage7m
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- 11. Radical Reactions2h 57m
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- Alcohol Nomenclature7m
- Ether Nomenclature11m
- Epoxide Nomenclature26m
- Thiol and Sulfide Nomenclature14m
- Synthesis of Alcohols Overview12m
- Leaving Group Conversions - Using HX11m
- Leaving Group Conversions - SOCl2 and PBr317m
- Leaving Group Conversions - Sulfonyl Chlorides8m
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- Williamson Ether Synthesis3m
- Making Ethers - Alcohol Condensation4m
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- Making Ethers - Acid-Catalyzed Alkoxylation6m
- Making Ethers - Cumulative Practice10m
- Cleavage of Ethers10m
- Alcohol Protecting Groups3m
- t-Butyl Ether Protecting Groups5m
- Silyl Ether Protecting Groups10m
- Sharpless Asymmetric Epoxidation15m
- Reactions of Thiols10m
- Oxidation of Sulfides8m
- 13. Alcohols and Carbonyl Compounds2h 17m
- 14. Synthetic Techniques1h 34m
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- Infrared Spectroscopy16m
- IR Spectroscopy - Frequencies31m
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- 1H Nuclear Magnetic Resonance - General Features10m
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- 1H NMR - Chemical Shifts24m
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- NMR Practice14m
- 13C NMR - General Features7m
- Structure Determination - Molecular Sentences55m
- Mass Spect - Introduction12m
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- 16. Conjugated Systems6h 41m
- Introduction to Conjugation15m
- Stability of Conjugated Intermediates5m
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- Reactions at the Allylic Position39m
- Conjugated Hydrohalogenation28m
- Diels-Alder Reaction - General Features12m
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- Basics of Molecular Orbital Theory10m
- Drawing Atomic Orbitals7m
- Drawing Molecular Orbitals19m
- Frontier Molecular Orbital Theory - Finding HOMO/LUMO4m
- Orbital Diagram:3-atoms- Allylic Ions14m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
- Orbital Diagram:5-atoms- Allylic Ions10m
- Orbital Diagram:6-atoms- 1,3,5-hexatriene13m
- Orbital Diagram:Excited States5m
- Intro to Pericyclic Reactions13m
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- Introduction to Sigmatropic Shifts19m
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- 18. Aromaticity2h 33m
- Aromaticity - Introduction8m
- Four Tests of Aromaticity10m
- Counting Pi Electrons7m
- Aromaticity of Hydrocarbons18m
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- Inscribed Polygon Method17m
- Benzene Nomenclature13m
- Acidity of Aromatic Hydrocarbons10m
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- 19. Reactions of Aromatics: EAS and Beyond5h 22m
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- EAS-o, p-Major Products5m
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- Blocking Groups - Sulfonic Acid12m
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- Side-Chain Halogenation6m
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- Reactions at Benzylic Positions32m
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- EAS – Sequence Groups10m
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- Diazonium Compounds – Replacements Reactions6m
- Diazo Compounds – Sequence Groups5m
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- SNAr Addition-Elimination Mechanism32m
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- 20. Phenols55m
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- Aldehyde Nomenclature8m
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- Intro to Redox9m
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- Weak Oxidative Cleavage7m
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- Nucleophilic Addition8m
- Cyanohydrins11m
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- Hydrates6m
- Hemiacetals9m
- Acetal12m
- Acetals as Protecting Groups16m
- Thioacetals and Raney Nickel Reduction6m
- Imines vs Enamines15m
- Addition of Ammonia Derivatives5m
- Wolff Kishner Reduction7m
- Baeyer-Villiger Oxidation40m
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- 22. Carboxylic Acid Derivatives: NAS3h 1m
- COOH Derivatives and Nucleophilic Acyl Substitution7m
- Carboxylic Acid Nomenclature11m
- Diacid Nomenclature6m
- Ester Nomenclature7m
- Nitrile Nomenclature3m
- Acid Chloride Nomenclature5m
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- Nucleophilic Acyl Substitution – The Three Rules18m
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- Lactones, Lactams and Cyclization Reactions12m
- Carbonation of Grignard Reagents5m
- Decarboxylation14m
- Review of Nitriles46m
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 50m
- Alpha Carbons and Tautomerization9m
- Tautomers of Dicarbonyl Compounds6m
- Enolates4m
- Acid-Catalyzed Alpha-Halogenation4m
- Base-Catalyzed Alpha-Halogenation3m
- Haloform Reaction8m
- Hell-Volhard-Zelinski Reaction3m
- Overview of α-Carbon Alkylations and Acylations6m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis12m
- 25. Condensation Chemistry2h 23m
- 26. Amines1h 43m
- 27. Heterocycles2h 0m
- Nomenclature of Heterocycles15m
- Acid-Base Properties of Nitrogen Heterocycles10m
- Reactions of Pyrrole, Furan, and Thiophene13m
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes16m
- Addition Reactions of Furan8m
- EAS Reactions of Pyridine17m
- SNAr Reactions of Pyridine18m
- Side-Chain Reactions of Substituted Pyridines20m
- 28. Carbohydrates6h 25m
- Monosaccharide20m
- Monosaccharides – D and L Isomerism9m
- Monosaccharides – Drawing Fischer Projections18m
- Monosaccharides – Common Structures8m
- Monosaccharides – Forming Cyclic Hemiacetals13m
- Monosaccharides – Cyclization19m
- Monosaccharides – Haworth Projections15m
- Monosaccharides – Mutarotation11m
- Monosaccharides – Epimerization9m
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- Monosaccharides – Alkylation10m
- Monosaccharides – Acylation10m
- Monosaccharides – O-Glycosides10m
- Monosaccharides – N-Glycosides22m
- Monosaccharides – Reduction (Alditols)14m
- Monosaccharides – Weak Oxidation (Aldonic Acid)9m
- Monosaccharides – Reducing Sugars25m
- Monosaccharides – Strong Oxidation (Aldaric Acid)11m
- Monosaccharides – Oxidative Cleavage (Periodic Acid)29m
- Monosaccharides – Osazones10m
- Monosaccharides – Modern Kiliani-Fischer Synthesis25m
- Monosaccharides – Wohl Degradation12m
- Monosaccharides – Ruff Degradation13m
- Condensation Into Disaccharide32m
- Polysaccharides11m
- 29. Amino Acids4h 20m
- Introduction to Proteins20m
- Amino Acid Configuration14m
- The 20 Amino Acids - Introduction14m
- Amino Acid Chart1h 14m
- Acid-Base Properties of Amino Acids35m
- Isoelectric Point15m
- Amino Acid Synthesis: HVZ Method12m
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis16m
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis13m
- Synthesis of Amino Acids: Strecker Synthesis13m
- Reactions of Amino Acids: Esterification7m
- Reactions of Amino Acids: Acylation3m
- Reactions of Amino Acids: Hydrogenolysis6m
- Reactions of Amino Acids: Ninhydrin Test11m
- 30. Peptides and Proteins2h 42m
- Peptides12m
- Primary Protein Structure4m
- Secondary Protein Structure17m
- Tertiary Protein Structure11m
- Disulfide Bonds17m
- Quaternary Protein Structure10m
- Summary of Protein Structure7m
- Intro to Peptide Sequencing2m
- Peptide Sequencing: Partial Hydrolysis25m
- Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide7m
- Peptide Sequencing: Edman Degradation28m
- Merrifield Solid-Phase Peptide Synthesis18m
- 31. Catalysis in Organic Reactions1h 30m
- 32. Lipids 2h 50m
- 33. The Organic Chemistry of Metabolic Pathways2h 52m
- Intro to Metabolism6m
- ATP and Energy6m
- Intro to Coenzymes3m
- Coenzymes in Metabolism16m
- Energy Production in Biochemical Pathways5m
- Intro to Glycolysis3m
- Catabolism of Carbohydrates: Glycolysis27m
- Glycolysis Summary15m
- Pyruvate Oxidation (Simplified)4m
- Anaerobic Respiration11m
- Catabolism of Fats: Glycerol Metabolism11m
- Intro to Citric Acid Cycle7m
- Structures of the Citric Acid Cycle19m
- The Citric Acid Cycle35m
- 34. Nucleic Acids1h 32m
- 35. Transition Metals6h 14m
- Electron Configuration of Elements45m
- Coordination Complexes20m
- Ligands24m
- Electron Counting10m
- The 18 and 16 Electron Rule13m
- Cross-Coupling General Reactions40m
- Heck Reaction40m
- Stille Reaction13m
- Suzuki Reaction25m
- Sonogashira Coupling Reaction17m
- Fukuyama Coupling Reaction15m
- Kumada Coupling Reaction13m
- Negishi Coupling Reaction16m
- Buchwald-Hartwig Amination Reaction19m
- Eglinton Reaction17m
- Catalytic Allylic Alkylation18m
- Alkene Metathesis23m
- 36. Synthetic Polymers1h 49m
- Introduction to Polymers6m
- Chain-Growth Polymers10m
- Radical Polymerization15m
- Cationic Polymerization8m
- Anionic Polymerization8m
- Polymer Stereochemistry3m
- Ziegler-Natta Polymerization4m
- Copolymers6m
- Step-Growth Polymers11m
- Step-Growth Polymers: Urethane6m
- Step-Growth Polymers: Polyurethane Mechanism10m
- Step-Growth Polymers: Epoxy Resin8m
- Polymers Structure and Properties8m
24. Enolate Chemistry: Reactions at the Alpha-Carbon
Enamine Alkylation and Acylation
3:03 minutesOpen Question
Provide the major product after each step for the following reaction.
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