Hey guys. So just to catch you up, now we've learned 2 different addition reactions that both add alcohol to double bonds. The first one was hydration and if you remember, that was a Markovnikov alcohol that could rearrange. Then we had oxymercuration. Remember that oxymerc was also a Markovnikov alcohol, but it couldn't rearrange because it didn't have a carbocation intermediate. Now what that's going to do is that's going to bring us to our 3rd way to add alcohol to a double bond, but this one is just going to be weird. It's just going to have a lot of difference from the other 2 and that's why it's going to be really useful to us because it's a very unique reaction. The name of this reaction is hydroboration oxidation. So let's go ahead and just learn the general features first. Okay? So first of all, the intermediate for hydroboration oxidation is not going to be a carbocation. It's actually going to be its own thing. It's going to be what we call a 4 membered concerted intermediate. Now I know that already sounds terrible. I'm going to explain to you guys how to draw it, but it is kind of weird. It's a very unique looking intermediate. Okay? By the way, this isn't considered one more thing, it's not considered an intermediate, it's actually considered a transition state. Okay? So that's another thing that you want to keep in mind. It's actually not an intermediate, it's a transition state. Okay? Now the stereochemistry for this is going to be very unique. It's actually going to be syn addition. Okay? Now remember that I told you guys for oxymerc that anti addition meant that you get trans products? Well, it's the same kind of thing for syn addition. All syn addition means is that you're going to get cis products. Okay? And once I show you the mechanism, that will make more sense. Okay? And then finally, what's the product going to be? Well, I already told you you're taking a double bond and you're making an alcohol out of it. So that part hasn't changed. The only thing is that the stereochemistry is changing and the intermediate or the transition state is changing. Okay? What else? Well, can this rearrange? Remember that what kind of intermediates like to rearrange? Carbocations. Do I have one? No. So we're not going to get any rearrangements here. Okay? Finally, this is probably the most interesting part of hydroboration. Hydroboration is going to be one of the only one of only 2 reactions we're going to learn that are anti-Markovnikov. Okay? So what that means is that it's going to prefer to add my alcohol to the least substituted position. And that's really only going to make sense once I explain the mechanism. Okay? But the reason this is important is because later on when we get into synthesis, synthesis is all about taking molecules and making them into what you want. So having a reaction that adds anti-mark is going to allow me to add to branches. It's going to allow me to add to things that are on the peripheral or on the outside of a molecule instead of the things that are towards the center. You're going to see what I mean by that later, but this is a very important reaction. Just keep that in mind. So let's go ahead and look at the general product of this reaction. I have that double bond that I've been using forever, the same double bond. And notice that I'm adding some interesting reagents. What I'm adding here is BH3 or it says other boron source. Okay? Like oxymercuration, this is also going to be a 2 part reaction. Where in the first part, I'm going to add my boron and that's going to be the part that I call hydroboration. Hydroboration, the word bor comes from the word boron. So when I see that, I Okay? Now, the thing that is a little bit complicated about hydroboration is that different textbooks and different professors might have their own source of boron that they want to use. Okay? So most typically that source of boron is going to be BH3 or another one that's very common is B2H6. Okay? Now what you'll notice is that the empirical formula of B2H6 is the same as BH3. That's just a dimer. That just means you have 2 BH3s together and it makes B2H6. Alright? If you see those things, they're the same thing. But some professors do get a little bit creative with this and they'll use some other reagents. So some other ones that I've seen that you should just be on the lookout for in case you have any online homework or in case you just want to like look this up with an online resource is one of them is catecholborane. This actually looks like this thing right here. You don't need to know how to draw it. Just recognize that catecholborane is one of the reagents that is used for this. Now I said you don't need to draw it unless this is the one your professor uses. If your professor is always using catecholborane, then obviously you should learn how to draw that. Okay? Another one is a molecule called 9-bbn, which honestly I'm not going to draw, but it is a molecule that has boron on it. And then finally, any molecule that has the molecular formula R2BH. Okay? So that just means any source of boron that has a boron with 2 R groups sticking off of it. Okay? All of these could be used for the hydroboration step. The one that you're going to use is just go to class and just make sure that you know which one your professor talked about in class. Okay? So that's the hydroboration step. Now we're going to go to the second step. After we hydroborate, we're going to oxidize. Okay? And we're going to use hydrogen peroxide with a base as our oxidizing step. Okay? So we don't know a whole lot about oxidation reduction yet, so I'm just going to leave it right there for now. Now check out what my end products are. What I've got now is that even without knowing the mechanism, I can predict what my product is going to look like. Remember that we said that I'm going to get an alcohol? That's anti-Markovnikov and that's syn. So what that means is that my alcohol should go down here to the less substituted carbon and it should be cis to the hydrogen that it adds. Okay? So notice that cis, notice that right here I had a methyl group. Okay? If that methyl group the reason that that methyl group is being faced up towards the wedge here is because on the double bond I added 2 things. Remember that every addition reaction adds 2 single bonds to the double bond. I'm going to get an H on one side and an OH on the other. And those 2 need to be cis to each other because it's syn addition. So that's why I've drawn it like this. So does that make sense so far? Basically, we've got anti-Markovnikov alcohol that has syn addition. Alright?
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
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- 1H NMR:Spin-Splitting Simple Tree Diagrams11m
- 1H NMR:Spin-Splitting Complex Tree Diagrams12m
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- 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
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- 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
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- Cumulative Electrocyclic Problems25m
- Sigmatropic Rearrangement17m
- Cope Rearrangement9m
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- 17. Ultraviolet Spectroscopy51m
- 18. Aromaticity2h 34m
- 19. Reactions of Aromatics: EAS and Beyond5h 1m
- Electrophilic Aromatic Substitution9m
- Benzene Reactions11m
- EAS:Halogenation Mechanism6m
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- EAS:Friedel-Crafts Acylation Mechanism5m
- EAS:Any Carbocation Mechanism7m
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- Blocking Groups - Sulfonic Acid12m
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- Birch Reduction10m
- EAS:Sequence Groups4m
- EAS:Retrosynthesis29m
- Diazo Replacement Reactions6m
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- 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
10. Addition Reactions
Hydroboration
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