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Draw the structures of products A and B in the following reaction sequence.
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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
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides
Hydrolysis of Thioesters
Scelta multipla
Which of the following is the major product formed by acid-catalyzed hydrolysis of a thioester lactone?
A
A and a
B
An and a
C
A and an
D
An and a
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Guida verificata passo dopo passo1
Recognize that a thioester lactone is a cyclic thioester, meaning it contains a sulfur atom bonded to a carbonyl carbon within a ring structure.
Understand that acid-catalyzed hydrolysis involves protonation of the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon and making it more susceptible to nucleophilic attack by water.
Identify that water acts as the nucleophile, attacking the protonated carbonyl carbon, leading to ring opening and formation of a tetrahedral intermediate.
Realize that the tetrahedral intermediate collapses, breaking the C–S bond (the thioester bond), which results in the formation of a carboxylic acid and a thiol as the products.
Conclude that the major products of acid-catalyzed hydrolysis of a thioester lactone are a carboxylic acid and a thiol, because the thioester bond is cleaved and the ring is opened.
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