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Organic Chemistry
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1. A Review of General Chemistry
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Worksheet
Summary
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Intro to Organic Chemistry
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Atomic Structure
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Wave Function
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Molecular Orbitals
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Sigma and Pi Bonds
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Octet Rule
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Bonding Preferences
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Formal Charges
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Skeletal Structure
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Lewis Structure
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Condensed Structural Formula
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Degrees of Unsaturation
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Constitutional Isomers
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Resonance Structures
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Hybridization
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Molecular Geometry
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Electronegativity
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2. Molecular Representations
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Worksheet
Intermolecular Forces
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How To Determine Solubility
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Functional Groups
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3. Acids and Bases
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Worksheet
Organic Chemistry Reactions
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Reaction Mechanism
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Acids and Bases
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Equilibrium Constant
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pKa
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Acid Base Equilibrium
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Ranking Acidity
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4. Alkanes and Cycloalkanes
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Worksheet
IUPAC Naming
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Alkyl Groups
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Naming Cycloalkanes
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Naming Bicyclic Compounds
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Naming Alkyl Halides
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Naming Alkenes
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Naming Alcohols
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Naming Amines
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Cis vs Trans
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Conformational Isomers
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Newman Projections
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Drawing Newman Projections
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Barrier To Rotation
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Ring Strain
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Axial vs Equatorial
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Cis vs Trans Conformations
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Equatorial Preference
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Chair Flip
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Calculating Energy Difference Between Chair Conformations
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A-Values
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Decalin
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5. Chirality
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Worksheet
Constitutional Isomers vs. Stereoisomers
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Chirality
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Test 1:Plane of Symmetry
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Test 2:Stereocenter Test
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R and S Configuration
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Enantiomers vs. Diastereomers
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Atropisomers
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Meso Compound
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Test 3:Disubstituted Cycloalkanes
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What is the Relationship Between Isomers?
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Fischer Projection
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R and S of Fischer Projections
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Optical Activity
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Enantiomeric Excess
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Calculations with Enantiomeric Percentages
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Non-Carbon Chiral Centers
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6. Thermodynamics and Kinetics
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Worksheet
Energy Diagram
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Gibbs Free Energy
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Enthalpy
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Entropy
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Hammond Postulate
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Carbocation Stability
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Carbocation Intermediate Rearrangements
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7. Substitution Reactions
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Worksheet
Nucleophilic Substitution
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Good Leaving Groups
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SN2 Reaction
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SN1 Reaction
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Substitution Comparison
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8. Elimination Reactions
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Worksheet
E2 Mechanism
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Beta Hydrogen
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E2 - Anti-Coplanar Requirement
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E2 - Cumulative Practice
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E1 Reaction
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Solvents
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Leaving Groups
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Nucleophiles and Basicity
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SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
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Cumulative Substitution/Elimination
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9. Alkenes and Alkynes
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Worksheet
Alkene Stability
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Zaitsev Rule
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Dehydrohalogenation
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Double Elimination
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Acetylide
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Hydrogenation of Alkynes
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Dehydration Reaction
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POCl3 Dehydration
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Alkynide Synthesis
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10. Addition Reactions
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Worksheet
Addition Reaction
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Markovnikov
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Hydrohalogenation
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Acid-Catalyzed Hydration
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Oxymercuration
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Hydroboration
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Hydrogenation
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Halogenation
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Halohydrin
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Carbene
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Epoxidation
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Epoxide Reactions
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Dihydroxylation
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Ozonolysis
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Ozonolysis Full Mechanism
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Oxidative Cleavage
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Alkyne Oxidative Cleavage
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Alkyne Hydrohalogenation
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Alkyne Halogenation
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Alkyne Hydration
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Alkyne Hydroboration
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11. Radical Reactions
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Worksheet
Radical Reaction
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Radical Stability
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Free Radical Halogenation
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Radical Selectivity
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Calculating Radical Yields
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Anti Markovnikov Addition of Br
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Free Radical Polymerization
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Allylic Bromination
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Radical Synthesis
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12. Alcohols, Ethers, Epoxides and Thiols
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Worksheet
Alcohol Nomenclature
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Naming Ethers
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Naming Epoxides
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Naming Thiols
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Alcohol Synthesis
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Leaving Group Conversions - Using HX
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Leaving Group Conversions - SOCl2 and PBr3
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Leaving Group Conversions - Sulfonyl Chlorides
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Leaving Group Conversions Summary
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Williamson Ether Synthesis
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Making Ethers - Alkoxymercuration
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Making Ethers - Alcohol Condensation
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Making Ethers - Acid-Catalyzed Alkoxylation
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Making Ethers - Cumulative Practice
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Ether Cleavage
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Alcohol Protecting Groups
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t-Butyl Ether Protecting Groups
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Silyl Ether Protecting Groups
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Sharpless Epoxidation
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Thiol Reactions
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Sulfide Oxidation
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13. Alcohols and Carbonyl Compounds
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Worksheet
Oxidizing and Reducing Agents
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Oxidizing Agent
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Reducing Agent
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Nucleophilic Addition
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Preparation of Organometallics
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Grignard Reaction
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Protecting Alcohols from Organometallics
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Organometallic Cumulative Practice
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14. Synthetic Techniques
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Worksheet
Synthetic Cheatsheet
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Moving Functionality
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Alkynide Alkylation
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Alkane Halogenation
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Retrosynthesis
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15. Analytical Techniques:IR, NMR, Mass Spect
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Worksheet
Purpose of Analytical Techniques
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Infrared Spectroscopy
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Infrared Spectroscopy Table
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IR Spect:Drawing Spectra
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IR Spect:Extra Practice
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NMR Spectroscopy
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1H NMR:Number of Signals
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1H NMR:Q-Test
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1H NMR:E/Z Diastereoisomerism
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H NMR Table
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1H NMR:Spin-Splitting (N + 1) Rule
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1H NMR:Spin-Splitting Simple Tree Diagrams
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1H NMR:Spin-Splitting Complex Tree Diagrams
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1H NMR:Spin-Splitting Patterns
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NMR Integration
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NMR Practice
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Carbon NMR
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Structure Determination without Mass Spect
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Mass Spectrometry
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Mass Spect:Fragmentation
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Mass Spect:Isotopes
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16. Conjugated Systems
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Worksheet
Conjugation Chemistry
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Stability of Conjugated Intermediates
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Allylic Halogenation
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Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
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Diels-Alder Reaction
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Diels-Alder Forming Bridged Products
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Diels-Alder Retrosynthesis
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Molecular Orbital Theory
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Drawing Atomic Orbitals
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Drawing Molecular Orbitals
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HOMO LUMO
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Orbital Diagram:3-atoms- Allylic Ions
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Orbital Diagram:4-atoms- 1,3-butadiene
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Orbital Diagram:5-atoms- Allylic Ions
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Orbital Diagram:6-atoms- 1,3,5-hexatriene
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Orbital Diagram:Excited States
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Pericyclic Reaction
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Thermal Cycloaddition Reactions
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Photochemical Cycloaddition Reactions
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Thermal Electrocyclic Reactions
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Photochemical Electrocyclic Reactions
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Cumulative Electrocyclic Problems
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Sigmatropic Rearrangement
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Cope Rearrangement
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Claisen Rearrangement
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17. Aromaticity
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Worksheet
Aromaticity
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Huckel's Rule
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Pi Electrons
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Aromatic Hydrocarbons
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Annulene
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Aromatic Heterocycles
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Frost Circle
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Naming Benzene Rings
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Acidity of Aromatic Hydrocarbons
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Basicity of Aromatic Heterocycles
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Ionization of Aromatics
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18. Reactions of Aromatics:EAS and Beyond
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Worksheet
Electrophilic Aromatic Substitution
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Benzene Reactions
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EAS:Halogenation Mechanism
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EAS:Nitration Mechanism
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EAS:Friedel-Crafts Alkylation Mechanism
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EAS:Friedel-Crafts Acylation Mechanism
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EAS:Any Carbocation Mechanism
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Electron Withdrawing Groups
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EAS:Ortho vs. Para Positions
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Acylation of Aniline
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Limitations of Friedel-Crafts Alkyation
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Advantages of Friedel-Crafts Acylation
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Blocking Groups - Sulfonic Acid
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EAS:Synergistic and Competitive Groups
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Side-Chain Halogenation
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Side-Chain Oxidation
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Birch Reduction
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EAS:Sequence Groups
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EAS:Retrosynthesis
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Diazo Replacement Reactions
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Diazo Sequence Groups
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Diazo Retrosynthesis
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Nucleophilic Aromatic Substitution
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Benzyne
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19. Aldehydes and Ketones:Nucleophilic Addition
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Worksheet
Naming Aldehydes
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Naming Ketones
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Oxidizing and Reducing Agents
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Oxidation of Alcohols
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Ozonolysis
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DIBAL
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Alkyne Hydration
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Nucleophilic Addition
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Cyanohydrin
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Organometallics on Ketones
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Overview of Nucleophilic Addition of Solvents
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Hydrates
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Hemiacetal
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Acetal
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Acetal Protecting Group
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Thioacetal
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Imine vs Enamine
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Addition of Amine Derivatives
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Wolff Kishner Reduction
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Baeyer-Villiger Oxidation
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Acid Chloride to Ketone
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Nitrile to Ketone
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Wittig Reaction
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Ketone and Aldehyde Synthesis Reactions
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20. Carboxylic Acid Derivatives:NAS
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Worksheet
Carboxylic Acid Derivatives
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Naming Carboxylic Acids
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Diacid Nomenclature
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Naming Esters
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Naming Nitriles
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Acid Chloride Nomenclature
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Naming Anhydrides
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Naming Amides
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Nucleophilic Acyl Substitution
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Carboxylic Acid to Acid Chloride
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Fischer Esterification
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Acid-Catalyzed Ester Hydrolysis
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Saponification
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Transesterification
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Lactones, Lactams and Cyclization Reactions
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Carboxylation
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Decarboxylation Mechanism
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21. Enolate Chemistry:Reactions at the Alpha-Carbon
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Worksheet
Tautomerization
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Tautomers of Dicarbonyl Compounds
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Enolate
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Acid-Catalyzed Alpha-Halogentation
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Base-Catalyzed Alpha-Halogentation
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Haloform Reaction
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Hell-Volhard-Zelinski Reaction
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Overview of Alpha-Alkylations and Acylations
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Enolate Alkylation and Acylation
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Enamine Alkylation and Acylation
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Beta-Dicarbonyl Synthesis Pathway
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Acetoacetic Ester Synthesis
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Malonic Ester Synthesis
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22. Condensation Chemistry
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Worksheet
Condensation Reactions
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Aldol Condensation
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Directed Condensations
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Crossed Aldol Condensation
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Claisen-Schmidt Condensation
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Claisen Condensation
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Intramolecular Aldol Condensation
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Conjugate Addition
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Michael Addition
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Robinson Annulation
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23. Amines
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Worksheet
Amine Alkylation
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Gabriel Synthesis
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Amines by Reduction
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Nitrogenous Nucleophiles
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Reductive Amination
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Curtius Rearrangement
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Hofmann Rearrangement
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Hofmann Elimination
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Cope Elimination
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24. Carbohydrates
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Worksheet
Monosaccharide
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Monosaccharides - D and L Isomerism
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Monosaccharides - Drawing Fischer Projections
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Monosaccharides - Common Structures
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Monosaccharides - Forming Cyclic Hemiacetals
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Monosaccharides - Cyclization
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Monosaccharides - Haworth Projections
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Mutarotation
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Epimerization
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Monosaccharides - Aldose-Ketose Rearrangement
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Monosaccharides - Alkylation
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Monosaccharides - Acylation
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Glycoside
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Monosaccharides - N-Glycosides
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Monosaccharides - Reduction (Alditols)
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Monosaccharides - Weak Oxidation (Aldonic Acid)
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Reducing Sugars
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Monosaccharides - Strong Oxidation (Aldaric Acid)
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Monosaccharides - Oxidative Cleavage
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Monosaccharides - Osazones
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Monosaccharides - Kiliani-Fischer
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Monosaccharides - Wohl Degradation
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Monosaccharides - Ruff Degradation
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Disaccharide
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Polysaccharide
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25. Phenols
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Worksheet
Phenol Acidity
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26. Amino Acids, Peptides, and Proteins
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Worksheet
Proteins and Amino Acids
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L and D Amino Acids
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Polar Amino Acids
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Amino Acid Chart
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Acid-Base Properties of Amino Acids
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Isoelectric Point
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27. Transition Metals
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Worksheet
Electron Configuration of Elements
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Coordination Complexes
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Ligands
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Electron Counting
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The 18 and 16 Electron Rule
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Cross-Coupling General Reactions
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Heck Reaction
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Stille Reaction
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Suzuki Reaction
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Sonogashira Coupling Reaction
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Fukuyama Coupling Reaction
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Kumada Coupling Reaction
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Negishi Coupling Reaction
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Buchwald-Hartwig Amination Reaction
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Eglinton Reaction
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26. Amino Acids, Peptides, and Proteins
Amino Acid Chart Practice Problems
26. Amino Acids, Peptides, and Proteins
Amino Acid Chart Practice Problems
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