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Triethylene glycol is one of the products obtained from the reaction of excess ethylene oxide and hydroxide ion. Propose a mechanism for its formation.
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Indice
- 1. A Review of General Chemistry6h 57m
- Orgo 1: Pre-Course Review25m
- What is Organic Chemistry?10m
- Atomic Structure24m
- Wave Function9m
- Molecular Orbital Theory25m
- Sigma and Pi Bonds19m
- Octet Rule25m
- Bonding Preferences21m
- Formal Charges11m
- Skeletal Structure19m
- Lewis Structure20m
- Condensed Structural Formula22m
- Index of Hydrogen Deficiency (Structural)30m
- 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
- Naming Alkenes8m
- Naming Alcohols14m
- Naming Amines13m
- Cis vs Trans21m
- Conformational Isomers13m
- Newman Projections14m
- Drawing Newman Projections16m
- Barrier To Rotation9m
- Ring Strain9m
- Axial vs Equatorial7m
- Cis vs Trans Conformations4m
- Equatorial Preference14m
- Chair Flip9m
- Calculating Energy Difference Between Chair Conformations26m
- 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 43m
- 7. Substitution Reactions2h 13m
- 8. Elimination Reactions2h 53m
- 9. Alkenes and Alkynes3h 2m
- 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
- Ozonolysis Full Mechanism24m
- Oxidative Cleavage3m
- Alkyne Oxidative Cleavage7m
- Alkyne Hydrohalogenation3m
- Alkyne Halogenation2m
- Alkyne Hydration10m
- Alkyne Hydroboration2m
- 11. Radical Reactions2h 57m
- 12. Alcohols, Ethers, Epoxides and Thiols3h 30m
- 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
- Leaving Group Conversions Summary5m
- Williamson Ether Synthesis3m
- Making Ethers - Alcohol Condensation4m
- Making Ethers - Alkoxymercuration4m
- 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
- 15. Analytical Techniques: IR, NMR, Mass Spect7h 14m
- Purpose of Analytical Techniques5m
- Infrared Spectroscopy16m
- IR Spectroscopy - Frequencies31m
- IR Spect: Drawing Spectra40m
- IR Spect: Extra Practice26m
- 1H Nuclear Magnetic Resonance - General Features10m
- 1H NMR - Total Number of Signals26m
- 1H NMR - Proton Relationships26m
- 1H NMR: E/Z Diastereoisomerism8m
- 1H NMR - Chemical Shifts24m
- 1H NMR - Spin-Splitting without J-Values22m
- 1H NMR: Spin-Splitting Simple Tree Diagrams11m
- 1H NMR: Spin-Splitting Complex Tree Diagrams12m
- 1H NMR Spin-Splitting - Common Patterns8m
- 1H NMR - Integration18m
- NMR Practice14m
- 13C NMR - General Features7m
- Structure Determination - Molecular Sentences55m
- Mass Spect - Introduction12m
- Mass Spect - Fragmentation28m
- Mass Spect - Common Isotopes27m
- 16. Conjugated Systems6h 41m
- Introduction to Conjugation15m
- Stability of Conjugated Intermediates5m
- Allylic Halogenation14m
- Reactions at the Allylic Position39m
- Conjugated Hydrohalogenation28m
- Diels-Alder Reaction - General Features12m
- Diels-Alder - Bridged Products11m
- Diels-Alder Retrosynthesis11m
- 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
- Thermal Cycloaddition Reactions29m
- Photochemical Cycloaddition Reactions26m
- Thermal Electrocyclic Reactions14m
- Photochemical Electrocyclic Reactions10m
- Cumulative Electrocyclic Reactions25m
- Introduction to Sigmatropic Shifts19m
- Cope Rearrangement9m
- Claisen Rearrangement16m
- 17. Ultraviolet Spectroscopy51m
- 18. Aromaticity2h 33m
- Aromaticity - Introduction8m
- Four Tests of Aromaticity10m
- Counting Pi Electrons7m
- Aromaticity of Hydrocarbons18m
- Aromaticity of Annulene17m
- Aromaticity of Heterocycles20m
- Inscribed Polygon Method17m
- Benzene Nomenclature13m
- Acidity of Aromatic Hydrocarbons10m
- Basicity of Aromatic Heterocycles10m
- Ionization of Aromatics18m
- 19. Reactions of Aromatics: EAS and Beyond5h 11m
- Electrophilic Aromatic Substitution – General Mechanism10m
- Electrophilic Aromatic Substitution – Reactions12m
- Generating Electrophiles – EAS Halogenation8m
- Generating Electrophiles – EAS Nitration10m
- Generating Electrophiles – Friedel-Crafts Alkylation7m
- Generating Electrophiles – Friedel-Crafts Acylation6m
- Generating Electrophiles – Any Carbocation7m
- EAS – Monosubstituted Benzene22m
- EAS-o, p-Major Products5m
- EAS – Protection of Aniline Derivatives10m
- Limitations of Friedel-Crafts Alkyation19m
- Advantages of Friedel-Crafts Acylation6m
- Blocking Groups - Sulfonic Acid12m
- EAS – Polysubstituted Benzene13m
- Side-Chain Halogenation6m
- Side-Chain Oxidation4m
- Reactions at Benzylic Positions32m
- Birch Reduction10m
- EAS:Sequence Groups4m
- EAS:Retrosynthesis29m
- Diazo Replacement Reactions6m
- Diazo Sequence Groups5m
- Diazo Retrosynthesis13m
- Nucleophilic Aromatic Substitution28m
- Benzyne16m
- 20. Phenols55m
- 21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
- Aldehyde Nomenclature8m
- Ketone Nomenclature7m
- Intro to Redox9m
- Oxidation28m
- Ozonolysis7m
- DIBAL5m
- Alkyne Hydration9m
- Nucleophilic Addition8m
- Cyanohydrin11m
- Organometallics on Ketones19m
- Overview of Nucleophilic Addition of Solvents13m
- Hydrates6m
- Hemiacetal9m
- Acetal12m
- Acetal Protecting Group16m
- Thioacetal6m
- Imine vs Enamine15m
- Addition of Amine Derivatives5m
- Wolff Kishner Reduction7m
- Baeyer-Villiger Oxidation39m
- Acid Chloride to Ketone7m
- Nitrile to Ketone9m
- Wittig Reaction18m
- Ketone and Aldehyde Synthesis Reactions14m
- 22. Carboxylic Acid Derivatives: NAS2h 51m
- Carboxylic Acid Derivatives7m
- Naming Carboxylic Acids9m
- Diacid Nomenclature6m
- Naming Esters5m
- Naming Nitriles3m
- Acid Chloride Nomenclature5m
- Naming Anhydrides7m
- Naming Amides5m
- Nucleophilic Acyl Substitution18m
- Carboxylic Acid to Acid Chloride6m
- Fischer Esterification5m
- Acid-Catalyzed Ester Hydrolysis4m
- Saponification3m
- Transesterification5m
- Lactones, Lactams and Cyclization Reactions10m
- Carboxylation5m
- Decarboxylation Mechanism14m
- Review of Nitriles46m
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 50m
- Tautomerization9m
- Tautomers of Dicarbonyl Compounds6m
- Enolate4m
- Acid-Catalyzed Alpha-Halogentation4m
- Base-Catalyzed Alpha-Halogentation3m
- Haloform Reaction8m
- Hell-Volhard-Zelinski Reaction3m
- Overview of Alpha-Alkylations and Acylations6m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis12m
- 25. Condensation Chemistry2h 9m
- 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. Carbohydrates5h 54m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
- Monosaccharides - Drawing Fischer Projections18m
- Monosaccharides - Common Structures6m
- Monosaccharides - Forming Cyclic Hemiacetals12m
- Monosaccharides - Cyclization18m
- Monosaccharides - Haworth Projections13m
- Mutarotation11m
- Epimerization9m
- Monosaccharides - Aldose-Ketose Rearrangement8m
- Monosaccharides - Alkylation10m
- Monosaccharides - Acylation8m
- Glycoside6m
- Monosaccharides - N-Glycosides18m
- Monosaccharides - Reduction (Alditols)12m
- Monosaccharides - Weak Oxidation (Aldonic Acid)7m
- Reducing Sugars23m
- Monosaccharides - Strong Oxidation (Aldaric Acid)11m
- Monosaccharides - Oxidative Cleavage27m
- Monosaccharides - Osazones10m
- Monosaccharides - Kiliani-Fischer23m
- Monosaccharides - Wohl Degradation12m
- Monosaccharides - Ruff Degradation12m
- Disaccharide30m
- Polysaccharide11m
- 29. Amino Acids4h 16m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart1h 14m
- Acid-Base Properties of Amino Acids33m
- Isoelectric Point14m
- 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
10. Addition Reactions
Epoxide Ring Opening
Scelta multipla
Predict the major, organic product for the following reaction.
A
B
C
D
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Guida verificata passo dopo passo1
Identify the starting material: The given structure is an epoxide, which is a three-membered cyclic ether.
Recognize the reaction conditions: The reaction involves NaOH in water, which suggests a basic hydrolysis of the epoxide.
Understand the mechanism: In basic conditions, the nucleophile (OH-) will attack the less hindered carbon of the epoxide, leading to ring opening.
Predict the stereochemistry: The attack by OH- will occur from the opposite side of the leaving group (epoxide oxygen), leading to an anti addition and inversion of configuration at the attacked carbon.
Determine the product: The reaction will yield a diol, with hydroxyl groups on adjacent carbons. Consider the stereochemistry to determine if the product is achiral, a pair of enantiomers, a meso compound, or a single stereoisomer.
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