Table of contents
- 1. A Review of General Chemistry
- Summary
- Intro to Organic Chemistry
- Atomic Structure
- Wave Function
- Molecular Orbitals
- Sigma and Pi Bonds
- Octet Rule
- Bonding Preferences
- Formal Charges
- Skeletal Structure
- Lewis Structure
- Condensed Structural Formula
- Degrees of Unsaturation
- Constitutional Isomers
- Resonance Structures
- Hybridization
- Molecular Geometry
- Electronegativity
- 2. Molecular Representations
- 3. Acids and Bases
- 4. Alkanes and Cycloalkanes
- IUPAC Naming
- Alkyl Groups
- Naming Cycloalkanes
- Naming Bicyclic Compounds
- Naming Alkyl Halides
- Naming Alkenes
- Naming Alcohols
- Naming Amines
- Cis vs Trans
- Conformational Isomers
- Newman Projections
- Drawing Newman Projections
- Barrier To Rotation
- Ring Strain
- Axial vs Equatorial
- Cis vs Trans Conformations
- Equatorial Preference
- Chair Flip
- Calculating Energy Difference Between Chair Conformations
- A-Values
- Decalin
- 5. Chirality
- Constitutional Isomers vs. Stereoisomers
- Chirality
- Test 1:Plane of Symmetry
- Test 2:Stereocenter Test
- R and S Configuration
- Enantiomers vs. Diastereomers
- Atropisomers
- Meso Compound
- Test 3:Disubstituted Cycloalkanes
- What is the Relationship Between Isomers?
- Fischer Projection
- R and S of Fischer Projections
- Optical Activity
- Enantiomeric Excess
- Calculations with Enantiomeric Percentages
- Non-Carbon Chiral Centers
- 6. Thermodynamics and Kinetics
- 7. Substitution Reactions
- 8. Elimination Reactions
- 9. Alkenes and Alkynes
- 10. Addition Reactions
- Addition Reaction
- Markovnikov
- Hydrohalogenation
- Acid-Catalyzed Hydration
- Oxymercuration
- Hydroboration
- Hydrogenation
- Halogenation
- Halohydrin
- Carbene
- Epoxidation
- Epoxide Reactions
- Dihydroxylation
- Ozonolysis
- Ozonolysis Full Mechanism
- Oxidative Cleavage
- Alkyne Oxidative Cleavage
- Alkyne Hydrohalogenation
- Alkyne Halogenation
- Alkyne Hydration
- Alkyne Hydroboration
- 11. Radical Reactions
- 12. Alcohols, Ethers, Epoxides and Thiols
- Alcohol Nomenclature
- Naming Ethers
- Naming Epoxides
- Naming Thiols
- Alcohol Synthesis
- Leaving Group Conversions - Using HX
- Leaving Group Conversions - SOCl2 and PBr3
- Leaving Group Conversions - Sulfonyl Chlorides
- Leaving Group Conversions Summary
- Williamson Ether Synthesis
- Making Ethers - Alkoxymercuration
- Making Ethers - Alcohol Condensation
- Making Ethers - Acid-Catalyzed Alkoxylation
- Making Ethers - Cumulative Practice
- Ether Cleavage
- Alcohol Protecting Groups
- t-Butyl Ether Protecting Groups
- Silyl Ether Protecting Groups
- Sharpless Epoxidation
- Thiol Reactions
- Sulfide Oxidation
- 13. Alcohols and Carbonyl Compounds
- 14. Synthetic Techniques
- 15. Analytical Techniques:IR, NMR, Mass Spect
- Purpose of Analytical Techniques
- Infrared Spectroscopy
- Infrared Spectroscopy Table
- IR Spect:Drawing Spectra
- IR Spect:Extra Practice
- NMR Spectroscopy
- 1H NMR:Number of Signals
- 1H NMR:Q-Test
- 1H NMR:E/Z Diastereoisomerism
- H NMR Table
- 1H NMR:Spin-Splitting (N + 1) Rule
- 1H NMR:Spin-Splitting Simple Tree Diagrams
- 1H NMR:Spin-Splitting Complex Tree Diagrams
- 1H NMR:Spin-Splitting Patterns
- NMR Integration
- NMR Practice
- Carbon NMR
- Structure Determination without Mass Spect
- Mass Spectrometry
- Mass Spect:Fragmentation
- Mass Spect:Isotopes
- 16. Conjugated Systems
- Conjugation Chemistry
- Stability of Conjugated Intermediates
- Allylic Halogenation
- Reactions at the Allylic Position
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
- Diels-Alder Reaction
- Diels-Alder Forming Bridged Products
- Diels-Alder Retrosynthesis
- Molecular Orbital Theory
- Drawing Atomic Orbitals
- Drawing Molecular Orbitals
- HOMO LUMO
- Orbital Diagram:3-atoms- Allylic Ions
- Orbital Diagram:4-atoms- 1,3-butadiene
- Orbital Diagram:5-atoms- Allylic Ions
- Orbital Diagram:6-atoms- 1,3,5-hexatriene
- Orbital Diagram:Excited States
- Pericyclic Reaction
- Thermal Cycloaddition Reactions
- Photochemical Cycloaddition Reactions
- Thermal Electrocyclic Reactions
- Photochemical Electrocyclic Reactions
- Cumulative Electrocyclic Problems
- Sigmatropic Rearrangement
- Cope Rearrangement
- Claisen Rearrangement
- 17. Ultraviolet Spectroscopy
- 18. Aromaticity
- 19. Reactions of Aromatics: EAS and Beyond
- Electrophilic Aromatic Substitution
- Benzene Reactions
- EAS:Halogenation Mechanism
- EAS:Nitration Mechanism
- EAS:Friedel-Crafts Alkylation Mechanism
- EAS:Friedel-Crafts Acylation Mechanism
- EAS:Any Carbocation Mechanism
- Electron Withdrawing Groups
- EAS:Ortho vs. Para Positions
- Acylation of Aniline
- Limitations of Friedel-Crafts Alkyation
- Advantages of Friedel-Crafts Acylation
- Blocking Groups - Sulfonic Acid
- EAS:Synergistic and Competitive Groups
- Side-Chain Halogenation
- Side-Chain Oxidation
- Reactions at Benzylic Positions
- Birch Reduction
- EAS:Sequence Groups
- EAS:Retrosynthesis
- Diazo Replacement Reactions
- Diazo Sequence Groups
- Diazo Retrosynthesis
- Nucleophilic Aromatic Substitution
- Benzyne
- 20. Phenols
- 21. Aldehydes and Ketones: Nucleophilic Addition
- Naming Aldehydes
- Naming Ketones
- Oxidizing and Reducing Agents
- Oxidation of Alcohols
- Ozonolysis
- DIBAL
- Alkyne Hydration
- Nucleophilic Addition
- Cyanohydrin
- Organometallics on Ketones
- Overview of Nucleophilic Addition of Solvents
- Hydrates
- Hemiacetal
- Acetal
- Acetal Protecting Group
- Thioacetal
- Imine vs Enamine
- Addition of Amine Derivatives
- Wolff Kishner Reduction
- Baeyer-Villiger Oxidation
- Acid Chloride to Ketone
- Nitrile to Ketone
- Wittig Reaction
- Ketone and Aldehyde Synthesis Reactions
- 22. Carboxylic Acid Derivatives: NAS
- Carboxylic Acid Derivatives
- Naming Carboxylic Acids
- Diacid Nomenclature
- Naming Esters
- Naming Nitriles
- Acid Chloride Nomenclature
- Naming Anhydrides
- Naming Amides
- Nucleophilic Acyl Substitution
- Carboxylic Acid to Acid Chloride
- Fischer Esterification
- Acid-Catalyzed Ester Hydrolysis
- Saponification
- Transesterification
- Lactones, Lactams and Cyclization Reactions
- Carboxylation
- Decarboxylation Mechanism
- Review of Nitriles
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon
- Tautomerization
- Tautomers of Dicarbonyl Compounds
- Enolate
- Acid-Catalyzed Alpha-Halogentation
- Base-Catalyzed Alpha-Halogentation
- Haloform Reaction
- Hell-Volhard-Zelinski Reaction
- Overview of Alpha-Alkylations and Acylations
- Enolate Alkylation and Acylation
- Enamine Alkylation and Acylation
- Beta-Dicarbonyl Synthesis Pathway
- Acetoacetic Ester Synthesis
- Malonic Ester Synthesis
- 25. Condensation Chemistry
- 26. Amines
- 27. Heterocycles
- Nomenclature of Heterocycles
- Acid-Base Properties of Nitrogen Heterocycles
- Reactions of Pyrrole, Furan, and Thiophene
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes
- Addition Reactions of Furan
- EAS Reactions of Pyridine
- SNAr Reactions of Pyridine
- Side-Chain Reactions of Substituted Pyridines
- 28. Carbohydrates
- Monosaccharide
- Monosaccharides - D and L Isomerism
- Monosaccharides - Drawing Fischer Projections
- Monosaccharides - Common Structures
- Monosaccharides - Forming Cyclic Hemiacetals
- Monosaccharides - Cyclization
- Monosaccharides - Haworth Projections
- Mutarotation
- Epimerization
- Monosaccharides - Aldose-Ketose Rearrangement
- Monosaccharides - Alkylation
- Monosaccharides - Acylation
- Glycoside
- Monosaccharides - N-Glycosides
- Monosaccharides - Reduction (Alditols)
- Monosaccharides - Weak Oxidation (Aldonic Acid)
- Reducing Sugars
- Monosaccharides - Strong Oxidation (Aldaric Acid)
- Monosaccharides - Oxidative Cleavage
- Monosaccharides - Osazones
- Monosaccharides - Kiliani-Fischer
- Monosaccharides - Wohl Degradation
- Monosaccharides - Ruff Degradation
- Disaccharide
- Polysaccharide
- 29. Amino Acids
- Proteins and Amino Acids
- L and D Amino Acids
- Polar Amino Acids
- Amino Acid Chart
- Acid-Base Properties of Amino Acids
- Isoelectric Point
- Amino Acid Synthesis: HVZ Method
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis
- Synthesis of Amino Acids: Strecker Synthesis
- Reactions of Amino Acids: Esterification
- Reactions of Amino Acids: Acylation
- Reactions of Amino Acids: Hydrogenolysis
- Reactions of Amino Acids: Ninhydrin Test
- 30. Peptides and Proteins
- Peptides
- Primary Protein Structure
- Secondary Protein Structure
- Tertiary Protein Structure
- Disulfide Bonds
- Quaternary Protein Structure
- Summary of Protein Structure
- Intro to Peptide Sequencing
- Peptide Sequencing: Partial Hydrolysis
- Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide
- Peptide Sequencing: Edman Degradation
- Merrifield Solid-Phase Peptide Synthesis
- 31. Catalysis in Organic Reactions
- 32. Lipids
- 33. The Organic Chemistry of Metabolic Pathways
- Intro to Metabolism
- ATP and Energy
- Intro to Coenzymes
- Coenzymes in Metabolism
- Energy Production in Biochemical Pathways
- Intro to Glycolysis
- Catabolism of Carbohydrates: Glycolysis
- Glycolysis Summary
- Pyruvate Oxidation (Simplified)
- Anaerobic Respiration
- Catabolism of Fats: Glycerol Metabolism
- Intro to Citric Acid Cycle
- Structures of the Citric Acid Cycle
- The Citric Acid Cycle
- 34. Nucleic Acids
- 35. Transition Metals
- Electron Configuration of Elements
- Coordination Complexes
- Ligands
- Electron Counting
- The 18 and 16 Electron Rule
- Cross-Coupling General Reactions
- Heck Reaction
- Stille Reaction
- Suzuki Reaction
- Sonogashira Coupling Reaction
- Fukuyama Coupling Reaction
- Kumada Coupling Reaction
- Negishi Coupling Reaction
- Buchwald-Hartwig Amination Reaction
- Eglinton Reaction
- Catalytic Allylic Alkylation
- Alkene Metathesis
- 36. Synthetic Polymers
- Introduction to Polymers
- Chain-Growth Polymers
- Radical Polymerization
- Cationic Polymerization
- Anionic Polymerization
- Polymer Stereochemistry
- Ziegler-Natta Polymerization
- Copolymers
- Step-Growth Polymers
- Step-Growth Polymers: Urethane
- Step-Growth Polymers: Polyurethane Mechanism
- Step-Growth Polymers: Epoxy Resin
- Polymers Structure and Properties
20. Phenols
Phenol Acidity
20. Phenols
Phenol Acidity
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Practice this topic
- Multiple Choice
Rank the following phenols in order of increasing acidity.
1449views20comments - Multiple ChoiceRank the following molecules in increasing order of acidity (least acidic to most acidic).714views
- Textbook Question
(•••) Benzoic acid and phenol are insoluble in water. When sodium bicarbonate is added to the water, benzoic acid dissolves, but phenol does not. The addition of sodium hydroxide causes both to dissolve. On the basis of these observations, estimate the pKₐ of phenol. [The pKₐ of H₂CO₃ is 6.4.]
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543views - Textbook QuestionThe following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble. (b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.715views
- Textbook QuestionThe following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble. (a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.740views1rank
- Textbook Question
Predict the products formed when m-cresol (m-methylphenol) reacts with (b) acetyl chloride,
753views