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OpenOChem
1.
Getting Started
Computer Requirements
"Action" Text
"Pitfall" Alert
"Take Note" Text
2D Structures in Content
3D Structures in Content
2D Structure Questions
Creating simple molecules
Drawing Atoms
Drawing Ions
Selection Questions - Molecules
Selection Questions - atoms
3D Structure Questions
3D Structure Questions - Cyclic Molecules
3D Model Kit
2.
Organic Chemistry 101
Introduction
Electron Configurations of Atoms
QM Description of Orbitals
Practice Time - Electron Configurations
Hybridization
Practice Time! - Hybridization
Formal Charge
Practice Time - Formal Charge
Acids-bases
Practice Time - Acids and Bases
Hydrogen Bonding is a Verb!
Your Progress
3.
First Semester Topics
Structure and Bonding
Chemical Intuition
Difficulty-in-organic-chemistry
Atomic Orbitals
Electron Configurations of Atoms
Practice Time - Structure and Bonding 1
Lewis Structures
Drawing Lewis Structures Guide
Valence Bond Theory
Hybridization
sp3 Hybridization in Methane
sp2 Hybridization in Ethene
sp Hybridization in Ethyne
Polar Covalent Bonds
Formal Charge
Practice Time - Structure and Bonding 2
Curved Arrow Notation
Resonance
Resonance
Resonance Between Two Atoms
Resonance Between Three Atoms
Resonance in Conjugated Systems
Practice Time! - Resonance
Resonance - Which contributes most?
Insignificant Contributors
Electrons behave like waves
MO Theory Intro
Rules of Thumb
Structural Representations
3D Structures - Tetrahedral Geometry of Methane
Condensed Structural Formulas
Drawing Tetraheral Structures on Computer
Drawing Ring Structures
Practice Time! - Structural Representations
Acids/Base and Reactions
Reactions
Acids Intro
Lewis Acids and Bases
pKa Scale
Structure and Acidity
Structure and Acidity II
Curved Arrows and Reactions
Energy Diagrams and Reactions
Energy Diagrams
Energy Diagrams - Example 1
Constructing Transition States
Nucleophiles
Electrophiles
Functional Groups
Alkanes and Cycloalkanes
Naming Alkanes
The Alkane Series
Alkyl Groups
Common Named Alkyl Groups
IUPAC Nomenclature of Alkenes
Conformations of Acyclic Alkanes
PES Ethane
PES Butane
Conformations of Cyclic Alkanes
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Drawing Chairs
Conformational Analysis
Stereochemistry
Chirality or Handedness
Enantiomers
Identifing Chiral Centers
You Try!
Determining R/S Configuration
Diastereomers
Meso Compounds
Measuring Chiral Purity
Chirality and Drugs
Chiral Synthesis
Alkenes and Addition Reactions
Application - BVO (Brominated Vegetable Oil)
E/Z and CIP
Stability of Alkenes
Hyperconjugation
H-X Addition to Alkenes: Hydrohalogenation
Practice Time - Hydrohalogenation
X2 Addition to Alkenes: Halogenation
HOX addition: Halohydrins
Practice Time - Halogenation
Hydroboration/Oxidation of Alkenes: Hydration
Practice Time - Hydroboration-Oxidation
Oxymercuration-Reduction: Hydration
Practice Time - Oxymercuration/Reduction
Oxidation
Reduction
Alkynes
H-X Addition to Alkynes
X2 Addition
Hydration
Alcohols and Alkyl Halides
E1-Elimination
E2-Elimination
Aliphatic Substitutions (SN1/SN2)
Introduction
Mechanisms
Solvent Effects
Effect of Substrate
Effect of the Nucleophile
Leaving Group Effects
Animation
Dienes, Allylic and Benzylic systems
Allyl Cations, Anions and Radicals
Allyl and Vinyl Groups
Allylic Halogenation
SN1 and SN2 Reactions of Allylic Halides and Tosylates
Diels Alder Reaction
Electrophilic Addition - 1,2 versus 1,4
Endo versus Exo Attack
4.
Second Semester Topics
Arenes and Aromaticity
Common Named Arenes
Nomenclature
Practice Time - Naming Arenes
Stability of Aromatics
Aromaticity H5P
Benzenes MO's
Huckel's 4n+2 Rule
Frosts Circle
Aromatic Ions
Aromatic Heterocycles
Reactions of Arenes
Electrophilic Aromatic Substitution
EAS-Halogenation
EAS-Nitration
Practice Time - Synthesis of Aniline
EAS-Alkylation
Practice Time - Friedel Crafts Alkylation
EAS-Acylation
Practice Time - Synthesis of Alkyl Arenes
EAS-Sulfonation
Practice Time - EAS
Effect on Rate and Orientation
Donation and Withdrawal of Electrons
Regiochemistry in EAS
Practice Time - Directing Group Effects
Steric Considerations
Synthesizing Poly-substituted Benzene's
NAS - Addition/Elimination
NAS - Elimination/Addition - Benzyne
Alcohols and Phenols
Naming Alcohols
Preparation of Alcohols
Reduction of Aldehydes and Ketones
Addition of Grignard and OrganoLithiums
Practice Time - Preparation of Alcohols
Reductions in Organic Chemistry
Reactions of Alcohols
Review Rxns. of Alcohols
Oxidation of Alcohols
Protection of Alcohols
Practice Time - Reactions of Alcohols
Structure and Properties
Ethers and Epoxides
Intro and Occurrence
Crown Ethers
Preparation of Ethers
Reactions of Ethers
Practice Time - Ethers
Preparation of Epoxides
Reactions of Epoxides - Acidic Ring Opening
Practice Time - Acidic Ring Opening
Reactions of Epoxides - Nucleophilic Ring Opening
Practice Time - Nucleophilic Ring opening
Application - Epoxidation in Reboxetine Synthesis
Application - Nucleophilic Epoxide Ring Opening in Crixivan Synthesis
Naming Ethers and Epoxides
Aldehydes and Ketones
Naming Aldehydes and Ketones
Practice Time - Naming Aldehydes/Ketones
Nucleophilic addition
Addition of Water - Gem Diols
Practice Time - Hydration of Ketones and Aldehydes
Addition of Alcohols - Hemiacetals and Acetals
Acetal Protecting Groups
Hemiacetals in Carbohydrates
Practice Time - Hemiacetals and Acetals
Addition of Amines - Imines
Addition of Amines - Enamines
Practice Time - Imines and Enamines
Application - Imatinab Enamine Synthesis
Addition of CN - Cyanohydrins
Practice Time - Cyanohydrins
Application - Isentress Synthesis
Addition of Ylides - Wittig Reaction
Practice Time - Wittig Olefination
Carboxylic Acids and Derivatives
Introduction to Carboxylic Acids
Naming Carboxylic Acids
Acidity of Carboxylic Acids
Practice Time - Carboxylic Acid Naming and Acidity
Preparation of Carboxylic Acids
Reactions of Carboxylic Acids
Nucleophilic Acyl Substitution
Mechanism of Acyl Substitution
Leaving Groups
Electrophilicity of Carboxylic Acids Derivatives.
Practice Time - Acyl Subsitution
Carboxylic Acids
Acid Halides
Anhydrides
Esters
Amides
Practice Time - Reactions of Carboxylic Acid Derivatives
Enols and Enolates
Introduction to Enols
Tautomerization
Reactions of Enols
Practice Time - Enols and Tautomerism
Intro to Enolates
Reactions of Enolates
Alpha Halogenation of Ketones and Aldehydes
Direct Alkylation of Enolates
Acetoacetic Ester Synthesis
Malonic Ester Synthesis
Practice Time - Alkylation of Enolates
Condensation Reactions
Aldol Reaction
Crossed Aldol
Aldol Dehydration (Elimination)
Claisen Condensation
Micheal Addition
Robinson Annulation
Robinson Annulation - Micheal Addition
Robinson Annulation - Aldol Condensation
5.
Spectroscopy - NMR, IR and UV
Spectroscopy
HNMR
Chemical Shift
Interpreting
Nuclear Spin
Equivalency
Intensity of Signals
Spin Spin Splitting
hnmr-p1
hnmr-p2
hnmr-p3
hnmr-p4
hnmr-p5
Alcohols
Alkanes
Alkynes
hnm-p6
Alkene NMR
IR - Infrared Spectroscopy
Intro to IR
Interpreting IR Spectra
UV - Ultraviolet Spectroscopy
Intro to UV Spectroscopy
6.
Mass Spectrometry
Intro to MS
MS Fragmentation
Interpreting MS
7.
General Chemistry
Significant Figures
Practice Time! Significant Figures
Spreadsheets - Getting Started
Spreadsheets - Charts and Trend lines
Standard Deviation
Standard Deviation Calculations
Factor Labels
Practice Time! - Factor Labels
Limiting Reagent Problem
Percent Composition
Molar Mass Calculation
Average Atomic Mass
Empirical Formula
Initial Rate Analysis
Practice Time! Initial Rate Analysis
Solving Equilibrium Problems with ICE
Practice Time! Equilibrium ICE Tables
Le Chatelier's
8.
Organic Chemistry Lab
9.
General Chemistry Lab
Lab Equipment Guide
Vernier Calipers
10.
Named Reactions
Luche Reaction (Reduction)
Negishi Coupling
Birch Reduction
Buchwald -Hartwig Amination
Suzuki Cross-Coupling
Sandmeyer Reaction
Mitsunobu Reaction
Staudinger Reaction (Reduction)
Sonogashira Coupling
Ullmann Reaction
Stille Coupling
11.
Reagents
12.
Question Of The Day
13.
Tutorials
Using OpenOChem's 2D Editor
Reaction Mechanisms (introduction)
Factor Labels
Acetylides and Synthesis
H5P Content
14.
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Second Semester Topics
Arenes and Aromaticity
Aromatic Heterocycles
Aromatic Heterocycles
Pyridine and Pyrimidine
Show C p Orbitals
Show N p orbital
Show N lone pair
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