Table of contents
- 1. A Review of General Chemistry(448)
- Summary(0)
- Intro to Organic Chemistry(7)
- Atomic Structure(19)
- Wave Function(0)
- Molecular Orbitals(12)
- Sigma and Pi Bonds(13)
- Octet Rule(3)
- Bonding Preferences(15)
- Formal Charges(27)
- Skeletal Structure(20)
- Lewis Structure(30)
- Condensed Structural Formula(35)
- Degrees of Unsaturation(31)
- Constitutional Isomers(15)
- Resonance Structures(91)
- Hybridization(35)
- Molecular Geometry(31)
- Electronegativity(64)
- 2. Molecular Representations(96)
- 3. Acids and Bases(439)
- 4. Alkanes and Cycloalkanes(435)
- IUPAC Naming(31)
- Alkyl Groups(22)
- Naming Cycloalkanes(18)
- Naming Bicyclic Compounds(3)
- Naming Alkyl Halides(26)
- Naming Alkenes(67)
- Naming Alcohols(22)
- Naming Amines(23)
- Cis vs Trans(84)
- Conformational Isomers(5)
- Newman Projections(17)
- Drawing Newman Projections(31)
- Barrier To Rotation(5)
- Ring Strain(5)
- Axial vs Equatorial(10)
- Cis vs Trans Conformations(12)
- Equatorial Preference(31)
- Chair Flip(7)
- Calculating Energy Difference Between Chair Conformations(9)
- A-Values(6)
- Decalin(1)
- 5. Chirality(307)
- Constitutional Isomers vs. Stereoisomers(63)
- Chirality(12)
- Test 1:Plane of Symmetry(11)
- Test 2:Stereocenter Test(13)
- R and S Configuration(69)
- Enantiomers vs. Diastereomers(6)
- Atropisomers(11)
- Meso Compound(1)
- Test 3:Disubstituted Cycloalkanes(9)
- What is the Relationship Between Isomers?(24)
- Fischer Projection(23)
- R and S of Fischer Projections(23)
- Optical Activity(16)
- Enantiomeric Excess(13)
- Calculations with Enantiomeric Percentages(11)
- Non-Carbon Chiral Centers(2)
- 6. Thermodynamics and Kinetics(204)
- 7. Substitution Reactions(260)
- 8. Elimination Reactions(233)
- 9. Alkenes and Alkynes(263)
- 10. Addition Reactions(696)
- Addition Reaction(8)
- Markovnikov(3)
- Hydrohalogenation(67)
- Acid-Catalyzed Hydration(55)
- Oxymercuration(29)
- Hydroboration(62)
- Hydrogenation(37)
- Halogenation(42)
- Halohydrin(49)
- Carbene(27)
- Epoxidation(30)
- Epoxide Reactions(57)
- Dihydroxylation(45)
- Ozonolysis(69)
- Ozonolysis Full Mechanism(1)
- Oxidative Cleavage(9)
- Alkyne Oxidative Cleavage(13)
- Alkyne Hydrohalogenation(14)
- Alkyne Halogenation(36)
- Alkyne Hydration(21)
- Alkyne Hydroboration(22)
- 11. Radical Reactions(237)
- 12. Alcohols, Ethers, Epoxides and Thiols(313)
- Alcohol Nomenclature(22)
- Naming Ethers(29)
- Naming Epoxides(9)
- Naming Thiols(5)
- Alcohol Synthesis(11)
- Leaving Group Conversions - Using HX(23)
- Leaving Group Conversions - SOCl2 and PBr3(16)
- Leaving Group Conversions - Sulfonyl Chlorides(29)
- Leaving Group Conversions Summary(19)
- Williamson Ether Synthesis(50)
- Making Ethers - Alkoxymercuration(7)
- Making Ethers - Alcohol Condensation(11)
- Making Ethers - Acid-Catalyzed Alkoxylation(18)
- Making Ethers - Cumulative Practice(8)
- Ether Cleavage(28)
- Alcohol Protecting Groups(1)
- t-Butyl Ether Protecting Groups(0)
- Silyl Ether Protecting Groups(9)
- Sharpless Epoxidation(2)
- Thiol Reactions(14)
- Sulfide Oxidation(2)
- 13. Alcohols and Carbonyl Compounds(410)
- 14. Synthetic Techniques(87)
- 15. Analytical Techniques:IR, NMR, Mass Spect(328)
- Purpose of Analytical Techniques(0)
- Infrared Spectroscopy(12)
- Infrared Spectroscopy Table(32)
- IR Spect:Drawing Spectra(14)
- IR Spect:Extra Practice(8)
- NMR Spectroscopy(6)
- 1H NMR:Number of Signals(16)
- 1H NMR:Q-Test(8)
- 1H NMR:E/Z Diastereoisomerism(1)
- H NMR Table(25)
- 1H NMR:Spin-Splitting (N + 1) Rule(20)
- 1H NMR:Spin-Splitting Simple Tree Diagrams(4)
- 1H NMR:Spin-Splitting Complex Tree Diagrams(8)
- 1H NMR:Spin-Splitting Patterns(5)
- NMR Integration(13)
- NMR Practice(43)
- Carbon NMR(45)
- Structure Determination without Mass Spect(11)
- Mass Spectrometry(9)
- Mass Spect:Fragmentation(40)
- Mass Spect:Isotopes(8)
- 16. Conjugated Systems(280)
- Conjugation Chemistry(45)
- Stability of Conjugated Intermediates(19)
- Allylic Halogenation(6)
- Reactions at the Allylic Position(0)
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)(30)
- Diels-Alder Reaction(38)
- Diels-Alder Forming Bridged Products(19)
- Diels-Alder Retrosynthesis(20)
- Molecular Orbital Theory(3)
- Drawing Atomic Orbitals(0)
- Drawing Molecular Orbitals(5)
- HOMO LUMO(13)
- Orbital Diagram:3-atoms- Allylic Ions(0)
- Orbital Diagram:4-atoms- 1,3-butadiene(0)
- Orbital Diagram:5-atoms- Allylic Ions(6)
- Orbital Diagram:6-atoms- 1,3,5-hexatriene(3)
- Orbital Diagram:Excited States(2)
- Pericyclic Reaction(1)
- Thermal Cycloaddition Reactions(6)
- Photochemical Cycloaddition Reactions(5)
- Thermal Electrocyclic Reactions(8)
- Photochemical Electrocyclic Reactions(8)
- Cumulative Electrocyclic Problems(12)
- Sigmatropic Rearrangement(16)
- Cope Rearrangement(5)
- Claisen Rearrangement(10)
- 17. Ultraviolet Spectroscopy(0)
- 18. Aromaticity(142)
- 19. Reactions of Aromatics: EAS and Beyond(296)
- Electrophilic Aromatic Substitution(11)
- Benzene Reactions(1)
- EAS:Halogenation Mechanism(12)
- EAS:Nitration Mechanism(11)
- EAS:Friedel-Crafts Alkylation Mechanism(11)
- EAS:Friedel-Crafts Acylation Mechanism(12)
- EAS:Any Carbocation Mechanism(5)
- Electron Withdrawing Groups(74)
- EAS:Ortho vs. Para Positions(2)
- Acylation of Aniline(1)
- Limitations of Friedel-Crafts Alkyation(2)
- Advantages of Friedel-Crafts Acylation(0)
- Blocking Groups - Sulfonic Acid(1)
- EAS:Synergistic and Competitive Groups(4)
- Side-Chain Halogenation(19)
- Side-Chain Oxidation(9)
- Reactions at Benzylic Positions(0)
- Birch Reduction(6)
- EAS:Sequence Groups(7)
- EAS:Retrosynthesis(57)
- Diazo Replacement Reactions(9)
- Diazo Sequence Groups(3)
- Diazo Retrosynthesis(7)
- Nucleophilic Aromatic Substitution(19)
- Benzyne(13)
- 20. Phenols(11)
- 21. Aldehydes and Ketones: Nucleophilic Addition(238)
- Naming Aldehydes(9)
- Naming Ketones(12)
- Oxidizing and Reducing Agents(2)
- Oxidation of Alcohols(3)
- Ozonolysis(0)
- DIBAL(10)
- Alkyne Hydration(1)
- Nucleophilic Addition(2)
- Cyanohydrin(4)
- Organometallics on Ketones(3)
- Overview of Nucleophilic Addition of Solvents(0)
- Hydrates(2)
- Hemiacetal(4)
- Acetal(17)
- Acetal Protecting Group(12)
- Thioacetal(0)
- Imine vs Enamine(111)
- Addition of Amine Derivatives(17)
- Wolff Kishner Reduction(8)
- Baeyer-Villiger Oxidation(0)
- Acid Chloride to Ketone(1)
- Nitrile to Ketone(5)
- Wittig Reaction(9)
- Ketone and Aldehyde Synthesis Reactions(6)
- 22. Carboxylic Acid Derivatives: NAS(326)
- Carboxylic Acid Derivatives(22)
- Naming Carboxylic Acids(17)
- Diacid Nomenclature(1)
- Naming Esters(11)
- Naming Nitriles(7)
- Acid Chloride Nomenclature(6)
- Naming Anhydrides(8)
- Naming Amides(14)
- Nucleophilic Acyl Substitution(112)
- Carboxylic Acid to Acid Chloride(17)
- Fischer Esterification(17)
- Acid-Catalyzed Ester Hydrolysis(33)
- Saponification(17)
- Transesterification(12)
- Lactones, Lactams and Cyclization Reactions(13)
- Carboxylation(13)
- Decarboxylation Mechanism(6)
- Review of Nitriles(0)
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides(0)
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon(101)
- Tautomerization(16)
- Tautomers of Dicarbonyl Compounds(4)
- Enolate(20)
- Acid-Catalyzed Alpha-Halogentation(7)
- Base-Catalyzed Alpha-Halogentation(1)
- Haloform Reaction(6)
- Hell-Volhard-Zelinski Reaction(4)
- Overview of Alpha-Alkylations and Acylations(1)
- Enolate Alkylation and Acylation(15)
- Enamine Alkylation and Acylation(7)
- Beta-Dicarbonyl Synthesis Pathway(1)
- Acetoacetic Ester Synthesis(8)
- Malonic Ester Synthesis(11)
- 25. Condensation Chemistry(154)
- 26. Amines(129)
- 27. Heterocycles(0)
- Nomenclature of Heterocycles(0)
- Acid-Base Properties of Nitrogen Heterocycles(0)
- Reactions of Pyrrole, Furan, and Thiophene(0)
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes(0)
- Addition Reactions of Furan(0)
- EAS Reactions of Pyridine(0)
- SNAr Reactions of Pyridine(0)
- Side-Chain Reactions of Substituted Pyridines(0)
- 28. Carbohydrates(163)
- Monosaccharide(9)
- Monosaccharides - D and L Isomerism(4)
- Monosaccharides - Drawing Fischer Projections(4)
- Monosaccharides - Common Structures(0)
- Monosaccharides - Forming Cyclic Hemiacetals(13)
- Monosaccharides - Cyclization(9)
- Monosaccharides - Haworth Projections(7)
- Mutarotation(7)
- Epimerization(7)
- Monosaccharides - Aldose-Ketose Rearrangement(5)
- Monosaccharides - Alkylation(9)
- Monosaccharides - Acylation(4)
- Glycoside(10)
- Monosaccharides - N-Glycosides(3)
- Monosaccharides - Reduction (Alditols)(6)
- Monosaccharides - Weak Oxidation (Aldonic Acid)(4)
- Reducing Sugars(10)
- Monosaccharides - Strong Oxidation (Aldaric Acid)(8)
- Monosaccharides - Oxidative Cleavage(0)
- Monosaccharides - Osazones(0)
- Monosaccharides - Kiliani-Fischer(4)
- Monosaccharides - Wohl Degradation(5)
- Monosaccharides - Ruff Degradation(12)
- Disaccharide(12)
- Polysaccharide(11)
- 29. Amino Acids(82)
- Proteins and Amino Acids(43)
- L and D Amino Acids(9)
- Polar Amino Acids(0)
- Amino Acid Chart(4)
- Acid-Base Properties of Amino Acids(16)
- Isoelectric Point(10)
- Amino Acid Synthesis: HVZ Method(0)
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis(0)
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis(0)
- Synthesis of Amino Acids: Strecker Synthesis(0)
- Reactions of Amino Acids: Esterification(0)
- Reactions of Amino Acids: Acylation(0)
- Reactions of Amino Acids: Hydrogenolysis(0)
- Reactions of Amino Acids: Ninhydrin Test(0)
- 30. Peptides and Proteins(0)
- Peptides(0)
- Primary Protein Structure(0)
- Secondary Protein Structure(0)
- Tertiary Protein Structure(0)
- Disulfide Bonds(0)
- Quaternary Protein Structure(0)
- Summary of Protein Structure(0)
- Intro to Peptide Sequencing(0)
- Peptide Sequencing: Partial Hydrolysis(0)
- Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide(0)
- Peptide Sequencing: Edman Degradation(0)
- Merrifield Solid-Phase Peptide Synthesis(0)
- 31. Catalysis in Organic Reactions(0)
- 32. Lipids (0)
- 34. Nucleic Acids(0)
- 35. Transition Metals(42)
- Electron Configuration of Elements(0)
- Coordination Complexes(0)
- Ligands(0)
- Electron Counting(0)
- The 18 and 16 Electron Rule(0)
- Cross-Coupling General Reactions(0)
- Heck Reaction(10)
- Stille Reaction(5)
- Suzuki Reaction(13)
- Sonogashira Coupling Reaction(5)
- Fukuyama Coupling Reaction(0)
- Kumada Coupling Reaction(0)
- Negishi Coupling Reaction(5)
- Buchwald-Hartwig Amination Reaction(4)
- Eglinton Reaction(0)
- 36. Synthetic Polymers(0)
- Introduction to Polymers(0)
- Chain-Growth Polymers(0)
- Radical Polymerization(0)
- Cationic Polymerization(0)
- Anionic Polymerization(0)
- Polymer Stereochemistry(0)
- Ziegler-Natta Polymerization(0)
- Copolymers(0)
- Step-Growth Polymers(0)
- Step-Growth Polymers: Urethane(0)
- Step-Growth Polymers: Polyurethane Mechanism(0)
- Step-Growth Polymers: Epoxy Resin(0)
- Polymers Structure and Properties(0)
21. Aldehydes and Ketones: Nucleophilic Addition
Imine vs Enamine
21. Aldehydes and Ketones: Nucleophilic Addition
Imine vs Enamine: Study with Video Lessons, Practice Problems & Examples
59PRACTICE PROBLEM
Draw a mechanism for the hydrolysis of the acetal given below in the presence of an acid.
Draw a mechanism for the hydrolysis of the acetal given below in the presence of an acid.