Textbook Question
In your own words, explain why it is not possible to make primary alkyl halides, such as 1-bromopentane, using the electrophilic addition of HCl or HBr to an alkene.
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Table of contents
- 1. A Review of General Chemistry5h 6m
- Summary23m
- Intro to Organic Chemistry4m
- Atomic Structure17m
- Wave Function9m
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- Formal Charges6m
- Skeletal Structure14m
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- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
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- 2. Molecular Representations1h 14m
- 3. Acids and Bases2h 46m
- 4. Alkanes and Cycloalkanes4h 17m
- IUPAC Naming29m
- Alkyl Groups13m
- Naming Cycloalkanes10m
- Naming Bicyclic Compounds10m
- Naming Alkyl Halides7m
- Naming Alkenes3m
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- 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
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- Optical Activity5m
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- 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 19m
- 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
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- Alkyne Hydroboration2m
- 11. Radical Reactions1h 58m
- 12. Alcohols, Ethers, Epoxides and Thiols2h 40m
- Alcohol Nomenclature4m
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- Naming Epoxides18m
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- Alcohol Synthesis7m
- Leaving Group Conversions - Using HX11m
- Leaving Group Conversions - SOCl2 and PBr313m
- Leaving Group Conversions - Sulfonyl Chlorides5m
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- Williamson Ether Synthesis3m
- Making Ethers - Alkoxymercuration4m
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- Making Ethers - Acid-Catalyzed Alkoxylation4m
- Making Ethers - Cumulative Practice10m
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- Thiol Reactions6m
- Sulfide Oxidation4m
- 13. Alcohols and Carbonyl Compounds2h 17m
- 14. Synthetic Techniques1h 26m
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- Infrared Spectroscopy16m
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- H NMR Table24m
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- NMR Integration18m
- NMR Practice14m
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- 16. Conjugated Systems6h 13m
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- Reactions at the Allylic Position39m
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- Diels-Alder Reaction9m
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- Orbital Diagram:3-atoms- Allylic Ions13m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
- Orbital Diagram:5-atoms- Allylic Ions10m
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- DIBAL5m
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- Overview of Nucleophilic Addition of Solvents13m
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- Imine vs Enamine15m
- Addition of Amine Derivatives5m
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- Wittig Reaction18m
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- 22. Carboxylic Acid Derivatives: NAS2h 51m
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- Diacid Nomenclature6m
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- Naming Nitriles3m
- Acid Chloride Nomenclature5m
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- Nucleophilic Acyl Substitution18m
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- Fischer Esterification5m
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- 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
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- 28. Carbohydrates5h 53m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
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- Mutarotation11m
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- Monosaccharides - N-Glycosides18m
- Monosaccharides - Reduction (Alditols)12m
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- Reducing Sugars23m
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- Monosaccharides - Oxidative Cleavage27m
- Monosaccharides - Osazones10m
- Monosaccharides - Kiliani-Fischer23m
- Monosaccharides - Wohl Degradation12m
- Monosaccharides - Ruff Degradation12m
- Disaccharide30m
- Polysaccharide11m
- 29. Amino Acids4h 20m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart1h 18m
- 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
Markovnikov
Multiple Choice
Which of the following reaction conditions results in Markovnikov addition to an unsymmetric alkene?
A
Addition of in the presence of peroxides
B
Addition of in the presence of and (oxymercuration-demercuration)
C
Addition of in the presence of followed by (hydroboration-oxidation)
D
Addition of in the presence of dilute
0 Comments
Verified step by step guidance1
Understand that Markovnikov addition refers to the regioselectivity where the proton (H\+) adds to the carbon of the double bond with more hydrogens, and the other part (e.g., OH) adds to the more substituted carbon.
Analyze the reaction conditions given: Addition of H2O in the presence of peroxides typically leads to anti-Markovnikov addition due to a radical mechanism.
Oxymercuration-demercuration (Hg2+ and OAc2) is known to give Markovnikov addition without carbocation rearrangement, so this is a strong candidate.
Hydroboration-oxidation (B2H6 followed by H2O2) results in anti-Markovnikov addition because the boron adds to the less substituted carbon.
Addition of H2O in the presence of dilute H2SO4 proceeds via a carbocation intermediate, which leads to Markovnikov addition due to the stability of the carbocation formed on the more substituted carbon.
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