Part 1
Summary
Part 2
Summary
General chemistry review
A review of hybrid orbitals, dot structures, electronegativity, and polarity
Organic structures and acid/base
bond-line structures, functional groups, formal charges, resonance structures, oxidation and reduction, acid/base chemistry
Alkanes and cycloalkanes
naming alkanes and cycloalkanes, conformations of alkanes and cycloalkanes, and free radical reactions
Stereochemistry
chirality, stereoisomers, assigning absolute configuration using the R,S system, optical activity, diastereomers, meso compounds, fischer projections
Substitution and elimination reactions
SN1, SN2, E1, E2, nucleophiles, nucleophilicity, basicity
Alkenes and alkynes
naming alkenes and alkynes, reactions of alkenes and alkynes, synthesis
Alcohols, ethers, epoxides, sulfides
alcohols, ethers, epoxides, thiols, sulfides
Conjugation, Diels-Alder, and MO theory
conjugation, conjugated dienes, addition reactions of conjugated dienes, diels-alder reaction, MO theory, color
Aromatic compounds
aromatic compounds, naming derivatives of benzene, electrophilic aromatic substitution reactions
Aldehydes and ketones
nomenclature and reactions of aldehydes and ketones
Carboxylic acids and derivatives
naming carboxylic acids, formation of carboxylic acid derivatives
Amines
nomenclature and reactions of amines
Hybridization
It's the liger of orbitals and essential to organic chemistry! In this tutorial, Sal discusses the hybridization of orbitals.
Dot structures
In this tutorial, Jay reminds you how to draw the dot structures of simple organic molecules.
Hybrid orbitals
In this tutorial, Jay goes over sp3, sp2, and sp hybridization.
Electronegativity
What is the most important concept to understand in undergraduate organic chemistry? Of course, it's electronegativity! In this tutorial, Jay explains the concept of electronegativity and shows how it applies to polarity, intermolecular forces, and physical properties.
Bond-line structures
Call them Bonds. Covalent Bonds. Smart chemists need time to stir (and shake) their solutions. In this tutorial, Jay explains how chemists use bond-line structures as a form of organic shorthand to skip time-consuming carbon and hydrogen atoms labeling. Watch this tutorial so you too can be in the Dr. Know.
Functional groups
In this tutorial, Jay puts the "fun" back into recognizing functional groups.
Formal charge and resonance
Positive and negative charges are everywhere in orgo! In this tutorial, Jay shows you how to assign formal charges to molecules and how to draw resonance structures.
Oxidation and reduction
LEO the Lion goes GERRRR!!!! If that is all that you remember about redox from general chemistry, then this tutorial is for you! Jay shows you how to assign oxidation states in organic molecules.
Acid/base
Do you remember the basics of acid/base chemistry? In this tutorial, Jay reminds you of a few definitions, shows you how the stability of the conjugate base affects the acidity of the molecule, and demonstrates the importance of pKa values.
Naming alkanes
In this tutorial, Sal shows how to name alkanes.
Conformations
In this tutorial, Sal draws Newman projections and also explains chair and boat conformations for cyclohexane.
Naming alkanes, cycloalkanes, and bicyclic compounds
Do you speak the language of organic chemistry? In this tutorial, Jay shows you how to be fluent in naming alkanes, cycloalkanes, and bicyclic compounds.
Conformations of alkanes and cycloalkanes
In this tutorial, Jay shows the different conformations of straight chain alkanes and cyclohexane.
Free radical reaction
In this tutorial, Sal introduces free radical reactions by showing the reaction of methane with chlorine.
Chirality and the R,S system
Are you right handed or sinister-handed? Have you ever thought that you might not be as attractive as you look in the mirror? Welcome to the world of chirality. In this tutorial, Sal explores molecules that have the same composition and bonding, but are fundamentally different because they are mirror images of each other (kind of like Tomax and Xamot--the Crimson Guard Commanders from GI Joe).
Chirality and absolute configuration
Mirror, mirror on the wall . . . who is the fairest stereoisomer of all? In this tutorial, Jay explains chirality and how to determine the absolute configuration at a chirality center.
Optical activity
In this tutorial, Jay explains the concept of optical activity and demonstrates how to calculate specific rotation and enantiomeric excess.
Diastereomers and meso compounds
In this tutorial, Sal and Jay define stereoisomers, diastereomers, and meso compounds.
Fischer projections
In this tutorial, Jay shows how to draw a fischer projection and how to assign an absolute configuration to a chirality center in a fischer projection.
SN1 vs SN2
In this tutorial, Sal analyzes the differences between SN1 and SN2 reactions.
Nucleophilicity and basicity
In this tutorial, Sal discusses the difference between nucleophilicity and basicity.
Elimination reactions
In this tutorial, Sal explains the difference between an E1 and an E2 elimination reaction.
SN1/SN2/E1/E2
In this tutorial, Sal compares the differences between E2, E1, SN2, and SN1 reactions.
SN1 and SN2
In this tutorial, Jay covers the definitions of nucleophile/electrophile, The Schwartz Rules (may the Schwartz be with you!), and the differences between SN1 and SN2 reactions.
E1 and E2 reactions
In this tutorial, Jay covers the E1 elimination mechanism, carbocation rearrangements, and the details of the E2 elimination reaction.
SN1/SN2/E1/E2
In this tutorial, Jay discusses the strength of a nucleophile and the differences between SN1, SN2, E1, and E2 reactions.
Naming alkenes
In this tutorial, Sal names alkenes and discusses the E-Z system.
Alkene reactions
In this tutorial, Sal introduces reaction mechanisms and demonstrates a few reactions of alkenes.
Alkene nomenclature
In this tutorial, Jay names alkenes, discusses the stability of alkenes, and introduces the E/Z system.
Alkene reactions
In this tutorial, Jay explains the addition reactions of alkenes.
Naming and preparing alkynes
In this tutorial, Jay covers the nomenclature and preparation of alkynes, the acidity of terminal alkynes, and the alkylation of alkynes.
Alkyne reactions
In this tutorial, Jay shows the reactions of alkynes.
Synthesis using alkynes
In this tutorial, Jay demonstrates how to use Dr. Schwartz's organic flowsheet to solve synthesis problems involving alkynes. Always remember, pain is temporary, orgo is forever!
Content
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sp3 Hybridized Orbitals and Sigma Bonds
sp3 Hybridized Orbitals and Sigma Bonds
Pi bonds and sp2 Hybridized Orbitals
Pi bonds and sp2 Hybridized Orbitals
dot structures I: single bonds
Summary
dot structures II: multiple bonds
Summary
sp3 hybrid orbitals
Summary
tetrahedral bond angle proof
Summary
sp2 hybrid orbitals
Summary
sp hybrid orbitals
Summary
more hybridization
Summary
electronegativity
Summary
electronegativity and intermolecular forces
Summary
bond-line structures
Correction: On the last example, I said double bond and then corrected myself by saying triple bond.
3-D bond-line structures
Summary
structural (constitutional) isomers
Summary
functional groups I
Summary
functional groups II
Summary
formal charge I
Summary
formal charge II
Summary
resonance structures I
Summary
resonance structures II
Summary
resonance structures III
Summary
oxidation states I
Summary
oxidation states II
Summary
Acid/Base Definitions
Bronsted-Lowry and Lewis Definitions
Ka and pKa Derivation
A review of Keq, Ka, and pKa
Stabilization of Conjugate Base I
electronegativity
Stabilization of Conjugate Base II
resonance structures
Stabilization of Conjugate Base III
Inductive effects on acidity
Stabilization of Conjugate Base IV
The effect of hybrid orbitals on acidity
Representing Structures of Organic Molecules
Summary
Naming Simple Alkanes
Summary
Naming Alkanes with Alkyl Groups
Summary
Correction - 2-Propylheptane should never be the name!
Summary
Common and Systematic Naming-Iso, Sec and Tert Prefixes
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Organic Chemistry Naming Examples 1
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Organic Chemistry Naming Examples 2
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Organic Chemistry Naming Examples 3
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Organic Chemistry Naming Examples 4
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Organic Chemistry Naming Examples 5
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Newman Projections
Summary
Newman Projections 2
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Chair and Boat Shapes for Cyclohexane
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Double Newman Diagram for Methcyclohexane
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alkane and cycloalkane nomenclature I
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alkane and cycloalkane nomenclature II
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alkane and cycloalkane nomenclature III
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bicyclic compounds
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naming cubane
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conformations of ethane and propane
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conformations of butane
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conformations of cyclohexane I: chair and boat
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conformations of cyclohexane II: monosubstituted
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conformations of cyclohexane III: disubstituted
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conformations of cyclohexane IV: trisubstituted
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Introduction to Chirality
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Chiral Examples 1
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Chiral Examples 2
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Cahn-Ingold-Prelog System for Naming Enantiomers
Summary
R,S (Cahn-Ingold-Prelog) Naming System Example 2
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chirality centers and stereoisomers
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R,S system for determining absolute configuration
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R,S system for cyclic compounds
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optical activity I: theory
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optical activity II: calculations
Summary
Stereoisomers, Enantiomers, Diastereomers, Constitutional Isomers and Meso Compounds
Summary
diastereomers
Summary
meso compounds
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Naming Alkyl Halides
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Sn2 Reactions
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Sn1 Reactions
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Steric hindrance
Summary
Sn2 Stereochemistry
Summary
Solvent Effects on Sn1 and Sn2 Reactions
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Nucleophilicity (Nucleophile Strength)
Summary
Nucleophilicity vs. Basicity
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E2 Reactions
Summary
E1 Reactions
Summary
Zaitsev's Rule
Summary
Comparing E2 E1 Sn2 Sn1 Reactions
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E2 E1 Sn2 Sn1 Reactions Example 2
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E2 E1 Sn2 Sn1 Reactions Example 3
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nucleophile/electrophile and The Schwartz Rules
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alkyl halide nomenclature
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SN1 reaction: mechanism
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SN1 reaction: stereochemistry
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SN2 mechanism and stereochemistry
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SN1 vs SN2: solvent effects
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SN1 vs SN2: summary
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E1 Elimination: mechanism
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E1 Elimination: regioselectivity and stereoselectivity
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carbocations and rearrangements
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E1 Elimination: carbocation rearrangements
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E2 Elimination: mechanism
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E2 Elimination: regioselectivity
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E2 Elimination: stereoselectivity
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E2 Elimination: stereospecificity
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E2 Elimination: substituted cyclohexanes
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nucleophilicity and basicity
Summary
SN1 SN2 E1 E2 reactions: primary and tertiary alkyl halides
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SN1 SN2 E1 E2 reactions: secondary alkyl halides
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Naming Alkenes Examples
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Cis-Trans and E-Z Naming Scheme for Alkenes
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Entgegen-Zusammen Naming Scheme for Alkenes Examples
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Introduction to Reaction Mechanisms
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Markovnikov's Rule and Carbocations
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Addition of Water (Acid-Catalyzed) Mechanism
Summary
Polymerization of Alkenes with Acid
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Content
Alkene intro and stability
Summary
Alkene nomenclature
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cis/trans and the E/Z system
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hydrogenation
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hydrohalogenation
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hydration
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halogenation
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halohydrin formation
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hydroboration-oxidation
Summary
epoxide formation and anti dihydroxylation
Summary
syn dihydroxylation
Summary
Ozonolysis
Alkene clevage using ozone
alkyne nomenclature
Summary
alkyne acidity and alkylation
Summary
preparation of alkynes
Summary
reduction of alkynes
Summary
hydrohalogenation of alkynes
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hydration of alkynes
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hydroboration-oxidation of alkynes
Summary
halogenation and ozonolysis of alkynes
Summary
Correction: I forgot to draw a negative charge next to the first iodide anion.
Note that if a terminal alkyne is produced, the strong base will deprotonate the alkyne to form an alkynide anion. A proton source (like H2O) must be added to regenerate the terminal alkyne.