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OpenOChem
1.
Getting Started
Introduction
Practice Times
Progress Pulse
2D Structures in Content
3D Structures in Content
Drawing 2D Structures
Drawing simple molecules
Drawing Atoms
Drawing Ions
Drawing Rings
Drawing Fused RIngs
Computer Requirements
2.
First Semester Topics
General Chemistry Review
Introduction
Electron Configurations of Atoms
QM Description of Orbitals
Practice Time - Electron Configurations
Hybridization
Strategy to Determine Hybridization
Practice Time! - Hybridization
Formal Charge
Practice Time - Formal Charge
Acids-bases
Practice Time - Acids and Bases
Hydrogen Bonding is a Verb!
Progress Pulse
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
Methane - Lewis structure
Ethane - Lewis structure
Ethene - Lewis structure
Acetone - Lewis structure
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
Drawing The Resonance Hybrid
Practice Time! - Drawing Resonance Hybrids
Resonance in Conjugated Systems
Practice Time! - Resonance
Resonance - Which contributes most?
Insignificant Contributors
Electrons behave like waves
MO Theory Intro
Structural Representations
3D Structures - Tetrahedral Geometry of Methane
Condensed Structural Formulas
Drawing Tetraheral Structures on Computer
Drawing Ring Structures
Practice Time! - Structural Representations
Progress Pulse
Acids/Base and Reactions
Reactions
Reaction Arrows: What do they mean?
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
Carbocation Stability
Hyperconjugation-carbocations
Radical Reactions
Practice Time! Mechanisms and Reactions
Energy Diagrams and Reactions
Energy Diagrams
Energy Diagrams - Example 1
Constructing Transition States
Practice Time! Drawing Transition States
Practice Time! - Energy Diagrams
Progress Pulse
Introduction to Retrosynthesis
Alkanes and Cycloalkanes
Introduction to Hydrocarbons and Alkanes
Occurrence
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
Relative Stability of Acyclic Alkanes
Physical Properties of Alkanes
Ranking Boiling Point and Solubility of Compounds
Conformations of Acyclic Alkanes
Newman and Sawhorse Projections
Torsional Strain
Hyperconjugation
Steric Strain
How to draw Newman projections
Dihedral Angles
PES Ethane
PES Butane
Practice Time! Conformations of acyclic alkanes.
Conformations of Cyclic Alkanes
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Drawing Chairs
Conformational Analysis
Naming Bicyclic Compounds
Stability of Cycloalkane (Combustion Analysis)
Degree of Unsaturation
Stereochemistry
Enalapril in ACE
Constitutional and Stereoisomers
Chirality or Handedness
Drawing a Molecules Mirror Image
Exploring Mirror Image Structures
Enantiomers
Drawing Enantiomers
Practice Time! Drawing Enantiomers
Identifying Chiral Centers
Practice Time! Identifying Chiral Molecules
CIP (Cahn-Ingold-Prelog) Priorities
Determining R/S Configuration
Diastereomers
Meso Compounds
Fischer Projections
Fischer Projections: Carbohydrates
Measuring Chiral Purity
Practice Time! - Determining Chiral Purity and ee
Chirality and Drugs
Chiral Synthesis
Prochirality
Converting Fischer Projections to Zig-zag Structures
Practice Time! - Assigning R/S Configurations
Alkenes and Addition Reactions
The Structure of Alkenes
Naming Alkenes
Health Insight - 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 and Reduction in Organic Chemistry
Oxidation
Epoxidation of Alkenes
Reduction
Capsaicin
Alkynes
H-X Addition to Alkynes
X2 Addition
Hydration
Alkyne Acidity and Acetylide Anions
Reactions of Acetylide Anions
Alcohols and Alkyl Halides
Naming Alkyl Halides
Naming Alcohols
Structure and Reactivity of Alcohols
Introduction to Substitution and Elimination Reactions
Preparation of Alkyl Halides and Tosylates
Preparation of Alcohols
E1-Elimination
E2-Elimination
Substitutions (SN1/SN2) and Eliminations (E1/E2)
Introduction
Mechanisms
Stereospecificity of SN1 and SN2 Reactions
Solvent Effects
Effect of Substrate
Effect of the Nucleophile
Leaving Group Effects
Animation
Application: Cardura (Doxazosin)
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
3.
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
Application: Cardura (Doxazosin) Amidation Step
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
4.
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
5.
General Chemistry
General Chemistry Lab
Lab Equipment Guide
Vernier Calipers
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
6.
Organic Chemistry Lab
Flash Chromatography
TLC
Distillation Setup
7.
Question Of The Day
8.
Tools and Reference
2D Editor
3D Model Kit
Periodic Table
pKa Values
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
Ritter Reaction
Rosenmund Reduction
Reagents
Heterocycles
Sig Fig Calculator
Molar Mass Calculator
Degree of Unsaturation Calculator
Newman Projection Tool
Bond Dissociation Energies
Fischer to Zigzag
Chromatograph Simulator
TLC Simulator
2D Editor (Copy)
9.
Tutorials
Using OpenOChem's 2D Editor
Reaction Mechanisms (introduction)
Factor Labels
Acetylides and Synthesis
Drawing Cyclohexane Chair Structures
Drawing Lewis Structures
Aromaticity Tutorial
Common Named Aromatics (Crossword Puzzle)
Functional Groups (Flashcards)
Alkyl and Alkenyl Groups
Clear History
Periodic Table
1
2.2
1s1
H
hydrogen
1.008
Legend
2
1s2
He
helium
4.0026
3
0.98
[He] 2s1
Li
lithium
6.94
4
1.57
[He] 2s2
Be
beryllium
9.0122
Atomic No.
Electronegativity
Electron Config.
C
Carbon
Atomic Mass
5
2.04
[He] 2s2 2p1
B
boron
10.81
6
2.55
[He] 2s2 2p2
C
carbon
12.011
7
3.04
[He] 2s2 2p3
N
nitrogen
14.007
8
3.44
[He] 2s2 2p4
O
oxygen
15.999
9
3.98
[He] 2s2 2p5
F
fluorine
18.998
10
[He] 2s2 2p6
Ne
neon
20.180
11
0.93
[Ne] 3s1
Na
sodium
22.990
12
1.31
[Ne] 3s2
Mg
magnesium
24.305
13
1.61
[Ne] 3s2 3p1
Al
aluminum
26.982
14
1.9
[Ne] 3s2 3p2
Si
silicon
28.085
15
2.19
[Ne] 3s2 3p3
P
phosphorus
30.974
16
2.58
[Ne] 3s2 3p4
S
sulfur
32.06
17
3.16
[Ne] 3s2 3p5
Cl
chlorine
35.45
18
[Ne] 3s2 3p6
Ar
argon
39.948
19
0.82
[Ar] 4s1
K
potassium
39.098
20
1
[Ar] 4s2
Ca
calcium
40.078
21
1.36
[Ar] 3d1 4s2
Sc
scandium
44.956
22
1.54
[Ar] 3d2 4s2
Ti
titanium
47.867
23
1.63
[Ar] 3d3 4s2
V
vanadium
50.942
24
1.66
[Ar] 3d5 4s1
Cr
chromium
51.996
25
1.55
[Ar] 3d5 4s2
Mn
manganese
54.938
26
1.83
[Ar] 3d6 4s2
Fe
iron
55.845
27
1.88
[Ar] 3d7 4s2
Co
cobalt
58.933
28
1.91
[Ar] 3d8 4s2
Ni
nickel
58.693
29
1.9
[Ar] 3d10 4s1
Cu
copper
63.546
30
1.65
[Ar] 3d10 4s2
Zn
zinc
65.38
31
1.81
[Ar] 3d10 4s2 4p1
Ga
gallium
69.723
32
2.01
[Ar] 3d10 4s2 4p2
Ge
germanium
72.63
33
2.18
[Ar] 3d10 4s2 4p3
As
arsenic
74.922
34
2.55
[Ar] 3d10 4s2 4p4
Se
selenium
78.96
35
2.96
[Ar] 3d10 4s2 4p5
Br
bromine
79.904
36
[Ar] 3d10 4s2 4p6
Kr
krypton
83.798
37
0.82
[Kr] 5s1
Rb
rubidium
85.468
38
0.95
[Kr] 5s2
Sr
sdivontium
87.62
39
1.22
[Kr] 4d1 5s2
Y
ytdivium
88.906
40
1.33
[Kr] 4d2 5s2
Zr
zirconium
91.224
41
1.6
[Kr] 4d4 5s1
Nb
niobium
92.906
42
2.16
[Kr] 4d5 5s1
Mo
molybdenum
95.96
43
1.9
[Kr] 4d5 5s2
Tc
technetium
[97.91]
44
2.2
[Kr] 4d7 5s1
Ru
ruthenium
101.07
45
2.28
[Kr] 4d8 5s1
Rh
rhodium
102.91
46
2.2
[Kr] 4d10
Pd
palladium
106.42
47
1.93
[Kr] 4d10 5s1
Ag
silver
107.87
48
1.69
[Kr] 4d10 5s2
Cd
cadmium
112.41
49
1.78
[Kr] 4d10 5s2 5p1
In
indium
114.82
50
1.96
[Kr] 4d10 5s2 5p2
Sn
tin
118.71
51
2.05
[Kr] 4d10 5s2 5p3
Sb
antimony
121.76
52
2.1
[Kr] 4d10 5s2 5p4
Te
tellurium
127.60
53
2.66
[Kr] 4d10 5s2 5p5
I
iodine
126.90
54
[Kr] 4d10 5s2 5p6
Xe
xenon
131.29
55
0.79
[Xe] 6s1
Cs
cesium
132.91
56
0.89
[Xe] 6s2
Ba
barium
137.33
72
1.3
[Xe] 4f14 5d2 6s2
Hf
hafnium
178.49
73
1.5
[Xe] 4f14 5d3 6s2
Ta
tantalum
180.95
74
2.36
[Xe] 4f14 5d4 6s2
W
tungsten
183.84
75
1.9
[Xe] 4f14 5d5 6s2
Re
rhenium
186.21
76
2.2
[Xe] 4f14 5d6 6s2
Os
osmium
190.23
77
2.2
[Xe] 4f14 5d7 6s2
Ir
iridium
192.22
78
2.28
[Xe] 4f14 5d9 6s1
Pt
platinum
195.08
79
2.54
[Xe] 4f14 5d10 6s1
Au
gold
196.97
80
2
[Xe] 4f14 5d10 6s2
Hg
mercury
200.59
81
2.04
[Xe] 4f14 5d10 6s2 6p1
Tl
thallium
204.38
82
2.33
[Xe] 4f14 5d10 6s2 6p2
Pb
lead
207.2
83
2.02
[Xe] 4f14 5d10 6s2 6p3
Bi
bismuth
208.98
84
2
[Xe] 4f14 5d10 6s2 6p4
Po
polonium
[208.98]
85
2.2
[Xe] 4f14 5d10 6s2 6p5
At
astatine
[209.99]
86
[Xe] 4f14 5d10 6s2 6p6
Rn
radon
[222.02]
87
0.7
[Rn] 7s1
Fr
francium
[223.02]
88
0.9
[Rn] 7s2
Ra
radium
[226.03]
104
[Rn] 5f14 6d2 7s2
Rf
rutherfordium
[265.12]
105
[Rn].5f14.6d3.7s2
Db
dubnium
[268.13]
106
[Rn].5f14.6d4.7s2
Sg
seaborgium
[271.13]
107
[Rn].5f14.6d5.7s2
Bh
bohrium
[270]
108
[Rn].5f14.6d6.7s2
Hs
hassium
[277.15]
109
[Rn].5f14.6d7.7s2
Mt
meitnerium
[276.15]
110
[Rn].5f14.6d9.7s1
Ds
darmstadtium
[281.16]
111
[Rn].5f14.6d10.7s1
Rg
roentgenium
[280.16]
112
[Rn].5f14.6d10.7s2
Cn
copernicium
[285.17]
113
[Rn].5f14.6d10.7s2.7p1
Uut
unundivium
[284.18]
114
[Rn].5f14.6d10.7s2.7p2
Fl
flerovium
[289.19]
115
[Rn].5f14.6d10.7s2.7p3
Uup
ununpentium
[288.19]
116
[Rn].5f14.6d10.7s2.7p4
Lv
livermorium
[293]
117
[Rn].5f14.6d10.7s2.7p5
Uus
ununseptium
[294]
118
[Rn].5f14.6d10.7s2.7p6
Uuo
ununoctium
[294]
57
1.1
[Xe] 5d1 6s2
La
lanthanum
138.91
58
1.12
[Xe] 4f1 5d1 6s2
Ce
cerium
140.12
59
1.13
[Xe] 4f3 6s2
Pr
praseodymium
140.91
60
1.14
[Xe] 4f4 6s2
Nd
neodymium
144.24
61
1.13
[Xe] 4f5 6s2
Pm
promethium
[144.91]
62
1.17
[Xe] 4f6 6s2
Sm
samarium
150.36
63
1.2
[Xe] 4f7 6s2
Eu
europium
151.96
64
1.2
[Xe] 4f7 5d1 6s2
Gd
gadolinium
157.25
65
1.2
[Xe] 4f9 6s2
Tb
terbium
158.93
66
1.22
[Xe] 4f10 6s2
Dy
dysprosium
162.50
67
1.23
[Xe] 4f11 6s2
Ho
holmium
164.93
68
1.24
[Xe] 4f12 6s2
Er
erbium
167.26
69
1.25
[Xe] 4f13 6s2
Tm
thulium
168.93
70
1.1
[Xe] 4f14 6s2
Yb
ytterbium
173.05
71
1.27
[Xe] 4f14 5d1 6s2
Lu
lutetium
174.97
89
1.1
[Rn] 6d1 7s2
Ac
actinium
[227.03]
90
1.3
[Rn] 6d2 7s2
Th
thorium
232.04
91
1.5
[Rn] 5f2 6d1 7s2
Pa
protactinium
231.04
92
1.38
[Rn] 5f3 6d1 7s2
U
uranium
238.03
93
1.36
[Rn] 5f4 6d1 7s2
Np
neptunium
[237.05]
94
1.28
[Rn] 5f6 7s2
Pu
plutonium
[244.06]
95
1.3
[Rn] 5f7 7s2
Am
americium
[243.06]
96
1.3
[Rn] 5f7 6d1 7s2
Cm
curium
[247.07]
97
1.3
[Rn] 5f9 7s2
Bk
berkelium
[247.07]
98
1.3
[Rn] 5f10 7s2
Cf
californium
[251.08]
99
1.3
[Rn] 5f11 7s2
Es
einsteinium
[252.08]
100
1.3
[Rn] 5f12 7s2
Fm
fermium
[257.10]
101
1.3
[Rn] 5f13 7s2
Md
mendelevium
[258.10]
102
1.3
[Rn] 5f14 7s2
No
nobelium
[259.10]
103
1.3
[Rn] 5f14 7s2 7p1
Lr
lawrencium
[262.11]
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