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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
Thermodynamics of Reactions
Acids Intro
Practice Time! Generating a conjugate base.
Lewis Acids and Bases
pKa Scale
Practice Time! pKa's
Predicting Acid-Base Reactions from pKa
Structure and Acidity
Structure and Acidity II
Practice Time! Structure and Acidity
Curved Arrows and Reactions
Nucleophiles
Electrophiles
Practice Time! Identifying Nucleophiles and Electrophiles
Mechanisms and Arrow Pushing
Proton Transfer (Acid/Base)
Nucleophilic Attack
Loss of Leaving Group
Rearrangements
Errors in Drawing Curved Arrows
Practice Time! Mechanisms and Reactions
Energy Diagrams and Reactions
Energy Diagrams
Energy Diagrams - Example 1
Constructing Transition States
Practice Time! - Energy Diagrams
Alkanes and Cycloalkanes
Functional Groups
Practice Time! Functional Groups.
Naming Alkanes
The Alkane Series
Alkyl Groups
Common Named Alkyl Groups
IUPAC Nomenclature of Alkanes
Practice Time! Naming Alkanes
Conformations of Acyclic Alkanes
Dihedral Angles
How to draw Newman projections
PES Ethane
PES Butane
Hyperconjugation
Practice Time! Conformations of acyclic alkanes.
Conformations of Cyclic Alkanes
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Drawing Chairs
Conformational Analysis
Stereochemistry
Constitutional and Stereoisomers
Chirality or Handedness
Drawing a Molecules Mirror Image
Enantiomers
Identifying Chiral Centers
Practice Time! Identifying Chiral Molecules
CIP (Cahn-Ingold-Prelog) Priorities and Configuration
Determining R/S Configuration
Diastereomers
Meso Compounds
Measuring Chiral Purity
Chirality and Drugs
Chiral Synthesis
Fischer Projections
Prochirality
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
Mass Spectrometry
Intro to MS
MS Fragmentation
Interpreting MS
6.
General Chemistry
Chapter 1 Essential Ideas
1.1 Chemistry in Context
1.2 Phases and Classification of Matter
1.3 Physical and Chemical Properties
1.4 Measurements
1.5 Measurement Uncertainty, Accuracy, and Precision
1.6 Mathematical Treatment of Measurement Results
Chapter 2 Atoms, Molecules, and Ions
Chapter 3 Electronic Structure and Periodic Properties of Elements
Chapter 4 Chemical Bonding and Molecular Geometry
Chapter 5 Advanced Theories of Bonding
Chapter 6 Composition of Substances and Solutions
Chapter 7 Stoichiometry of Chemical Reactions
Chapter 8 Gases
Chapter 9 Thermochemistry
Chapter 10 Liquids and Solids
Chapter 11 Solutions and Colloids
Chapter 12 Thermodynamics
Chapter 13 Fundamental Equilibrium Concepts
Chapter 14 Acid-Base Equilibria
Chapter 15 Equilibria of Other Reaction Classes
Chapter 16 Electrochemistry
Chapter 17 Kinetics
Chapter 18 Representative Metals, Metalloids, and Nonmetals
Chapter 19 Transition Metals and Coordination Chemistry
Chapter 20 Nuclear Chemistry
Chapter 21 Organic 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
Practice time! Empirical and Molecular Formulae
Initial Rate Analysis
Practice Time! Initial Rate Analysis
Solving Equilibrium Problems with ICE
Practice Time! Equilibrium ICE Tables
Le Chatelier's
Practice Time! Le Chatelier's Principle
7.
Organic Chemistry Lab
8.
General Chemistry Lab
Lab Equipment Guide
Vernier Calipers
9.
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
10.
Reagents
11.
Question Of The Day
12.
Tutorials
Using OpenOChem's 2D Editor
Reaction Mechanisms (introduction)
Factor Labels
Acetylides and Synthesis
H5P Content
13.
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General Chemistry
Chapter 1 Essential Ideas
1.4 Measurements
1.4 Measurements
Reading
1.4
Measurements