Cool so far, right? Now, the challenge becomes how do we name these guys because sometimes, first of all, they're not always three-membered rings. And second of all, there are a lot of substituents. So it turns out that there are 3 different common ways to name epoxides and I'm going to go over all of them right now. Let's start off with what we call the cycloalkane convention. In this type of naming system, what we do is we name the entire ring as if it was an alkane first. Okay? So as you can see here, I have a 6-membered ring. But how many of those atoms are actually carbons? Only 5 of them are. I've got 1, 2, 3, 4, 5. Now you might be wondering why I started the one there. I didn't need to. I'm just using that. I mean maybe I did, but I'm just using that as an example right now just to count carbons. Okay? So I have 5 carbons, but what I'm telling you is that we should actually name it as a cycloalkane, not by the number of carbons. So what that means is that usually when we're naming an alkane, we would say there are 5 carbons, so this would be cyclopentane. But it's not. We're going to call this actually cyclohexane because we go by the shape. What we're worried about here is the shape of the molecule, not how many carbons it has in it. So this would be a cyclohexane first of all as our root. Now the difference is if we have oxygens inside of a ring, which is by definition a cyclic ether, right? Then we're going to add the prefix oxa. And what oxa is going to tell us is that there is one member of this ring that is an oxygen. Okay? So if I call it oxacyclohexane, what I'm saying is that I have a 6-membered ring where one of the atoms is an oxygen, not a carbon. Okay? And then obviously location if necessary. So let's go ahead and just talk about this for a second. The root is going to be the oxacyclohexane. I have that written here. Now we just have to talk about locations. How do we know where to put those guys? Well, it turns out that the oxygen is always going to get your one spot. So when I put the one here, that didn't really count. That wasn't true numbering. The way that I should really number it is starting from the oxygen because that's the highest priority atom inside the ring. And then obviously, I should number to give the lowest overall number or to go to the next highest priority, Okay? So this would be 3-methyl-one oxacyclohexane. Cool so far? Just so you guys know, this also applies to rings that have more than 1 oxygen. If I had 2 oxygens, that would be what was called a dioxa. Okay? Just putting that out there, you could use prefixes as well. Okay? So now let's go ahead and talk about another naming system. This is going to be commonly used for non-three-membered rings. So if not three-membered as you can see, I was dealing with a 6-membered one here. This is usually the one we use. Okay? So if it's 4-membered, 5-membered, 6-membered, etcetera, you would use this naming system. Now, if it is a 3-membered ring, we could still use it but this is not going to be the most common way to name it. Okay?
Table of contents
- 1. A Review of General Chemistry5h 5m
- Summary23m
- Intro to Organic Chemistry5m
- Atomic Structure16m
- Wave Function9m
- Molecular Orbitals17m
- Sigma and Pi Bonds9m
- Octet Rule12m
- Bonding Preferences12m
- Formal Charges6m
- Skeletal Structure14m
- Lewis Structure20m
- Condensed Structural Formula15m
- Degrees of Unsaturation15m
- Constitutional Isomers14m
- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
- Electronegativity22m
- 2. Molecular Representations1h 14m
- 3. Acids and Bases2h 46m
- 4. Alkanes and Cycloalkanes4h 19m
- IUPAC Naming29m
- Alkyl Groups13m
- Naming Cycloalkanes10m
- Naming Bicyclic Compounds10m
- Naming Alkyl Halides7m
- Naming Alkenes3m
- Naming Alcohols8m
- Naming Amines15m
- Cis vs Trans21m
- Conformational Isomers13m
- Newman Projections14m
- Drawing Newman Projections16m
- Barrier To Rotation7m
- Ring Strain8m
- Axial vs Equatorial7m
- Cis vs Trans Conformations4m
- Equatorial Preference14m
- Chair Flip9m
- Calculating Energy Difference Between Chair Conformations17m
- A-Values17m
- Decalin7m
- 5. Chirality3h 39m
- Constitutional Isomers vs. Stereoisomers9m
- Chirality12m
- Test 1:Plane of Symmetry7m
- Test 2:Stereocenter Test17m
- R and S Configuration43m
- Enantiomers vs. Diastereomers13m
- Atropisomers9m
- Meso Compound12m
- Test 3:Disubstituted Cycloalkanes13m
- What is the Relationship Between Isomers?16m
- Fischer Projection10m
- R and S of Fischer Projections7m
- Optical Activity5m
- Enantiomeric Excess20m
- Calculations with Enantiomeric Percentages11m
- Non-Carbon Chiral Centers8m
- 6. Thermodynamics and Kinetics1h 22m
- 7. Substitution Reactions1h 48m
- 8. Elimination Reactions2h 30m
- 9. Alkenes and Alkynes2h 9m
- 10. Addition Reactions3h 18m
- Addition Reaction6m
- Markovnikov5m
- Hydrohalogenation6m
- Acid-Catalyzed Hydration17m
- Oxymercuration15m
- Hydroboration26m
- Hydrogenation6m
- Halogenation6m
- Halohydrin12m
- Carbene12m
- Epoxidation8m
- Epoxide Reactions9m
- Dihydroxylation8m
- Ozonolysis7m
- Ozonolysis Full Mechanism24m
- Oxidative Cleavage3m
- Alkyne Oxidative Cleavage6m
- Alkyne Hydrohalogenation3m
- Alkyne Halogenation2m
- Alkyne Hydration6m
- Alkyne Hydroboration2m
- 11. Radical Reactions1h 58m
- 12. Alcohols, Ethers, Epoxides and Thiols2h 42m
- Alcohol Nomenclature4m
- Naming Ethers6m
- Naming Epoxides18m
- Naming Thiols11m
- Alcohol Synthesis7m
- Leaving Group Conversions - Using HX11m
- Leaving Group Conversions - SOCl2 and PBr313m
- Leaving Group Conversions - Sulfonyl Chlorides7m
- Leaving Group Conversions Summary4m
- Williamson Ether Synthesis3m
- Making Ethers - Alkoxymercuration4m
- Making Ethers - Alcohol Condensation4m
- Making Ethers - Acid-Catalyzed Alkoxylation4m
- Making Ethers - Cumulative Practice10m
- Ether Cleavage8m
- Alcohol Protecting Groups3m
- t-Butyl Ether Protecting Groups5m
- Silyl Ether Protecting Groups10m
- Sharpless Epoxidation9m
- Thiol Reactions6m
- Sulfide Oxidation4m
- 13. Alcohols and Carbonyl Compounds2h 17m
- 14. Synthetic Techniques1h 26m
- 15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
- Purpose of Analytical Techniques5m
- Infrared Spectroscopy16m
- Infrared Spectroscopy Table31m
- IR Spect:Drawing Spectra40m
- IR Spect:Extra Practice26m
- NMR Spectroscopy10m
- 1H NMR:Number of Signals26m
- 1H NMR:Q-Test26m
- 1H NMR:E/Z Diastereoisomerism8m
- H NMR Table24m
- 1H NMR:Spin-Splitting (N + 1) Rule22m
- 1H NMR:Spin-Splitting Simple Tree Diagrams11m
- 1H NMR:Spin-Splitting Complex Tree Diagrams12m
- 1H NMR:Spin-Splitting Patterns8m
- NMR Integration18m
- NMR Practice14m
- Carbon NMR4m
- Structure Determination without Mass Spect47m
- Mass Spectrometry12m
- Mass Spect:Fragmentation28m
- Mass Spect:Isotopes27m
- 16. Conjugated Systems6h 13m
- Conjugation Chemistry13m
- Stability of Conjugated Intermediates4m
- Allylic Halogenation12m
- Reactions at the Allylic Position39m
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)26m
- Diels-Alder Reaction9m
- Diels-Alder Forming Bridged Products11m
- Diels-Alder Retrosynthesis8m
- Molecular Orbital Theory9m
- Drawing Atomic Orbitals6m
- Drawing Molecular Orbitals17m
- HOMO LUMO4m
- Orbital Diagram:3-atoms- Allylic Ions13m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
- Orbital Diagram:5-atoms- Allylic Ions10m
- Orbital Diagram:6-atoms- 1,3,5-hexatriene13m
- Orbital Diagram:Excited States4m
- Pericyclic Reaction10m
- Thermal Cycloaddition Reactions26m
- Photochemical Cycloaddition Reactions26m
- Thermal Electrocyclic Reactions14m
- Photochemical Electrocyclic Reactions10m
- Cumulative Electrocyclic Problems25m
- Sigmatropic Rearrangement17m
- Cope Rearrangement9m
- Claisen Rearrangement15m
- 17. Ultraviolet Spectroscopy51m
- 18. Aromaticity2h 34m
- 19. Reactions of Aromatics: EAS and Beyond5h 1m
- Electrophilic Aromatic Substitution9m
- Benzene Reactions11m
- EAS:Halogenation Mechanism6m
- EAS:Nitration Mechanism9m
- EAS:Friedel-Crafts Alkylation Mechanism6m
- EAS:Friedel-Crafts Acylation Mechanism5m
- EAS:Any Carbocation Mechanism7m
- Electron Withdrawing Groups22m
- EAS:Ortho vs. Para Positions4m
- Acylation of Aniline9m
- Limitations of Friedel-Crafts Alkyation19m
- Advantages of Friedel-Crafts Acylation6m
- Blocking Groups - Sulfonic Acid12m
- EAS:Synergistic and Competitive Groups13m
- Side-Chain Halogenation6m
- Side-Chain Oxidation4m
- Reactions at Benzylic Positions31m
- 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
- Naming Aldehydes8m
- Naming Ketones7m
- Oxidizing and Reducing Agents9m
- Oxidation of Alcohols28m
- 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 53m
- 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 Acylations5m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis15m
- 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 53m
- 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 - Acylation7m
- 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 Acids3h 20m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart18m
- 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
12. Alcohols, Ethers, Epoxides and Thiols
Naming Epoxides
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