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!
Alcohol nomenclature and properties
It can clean a wound or kill your liver. Some religions ban it, others use it in their sacred rites. Some of the most stupid acts humanity every committed were done under its influence. It is even responsible for some of our births. In this tutorial, Sal and Jay name alcohols and discuss their properties.
Synthesis of alcohols
In this tutorial, Jay shows how to synthesize alcohols using sodium borohydride, lithium aluminum hydride, and grignard reagents.
Reactions of alcohols
In this tutorial, Jay assigns oxidation states to alcohols, shows an oxidation mechanism using the Jones reagent, shows the formation of nitrate esters from alcohols, and demonstrates how to make alkyl halides from alcohols. Biochemical redox reactions are also discussed.
Nomenclature and properties of ethers
In this tutorial, Sal and Jay name ethers and discuss the physical properties of ethers.
Synthesis and cleavage of ethers
In this tutorial, Jay shows how to synthesize ethers using the Williamson ether synthesis and how to cleave an ether linkage using acid.
Nomenclature and preparation of epoxides
In this tutorial, Sal and Jay name epoxides. Jay also shows the preparation of epoxides and includes the stereochemistry of the reaction.
Ring-opening reactions of epoxides
In this tutorial, Sal and Jay show the SN1 and SN2 ring opening reactions of epoxides.
Thiols and sulfides
In this tutorial, Jay shows how to prepare sulfides from thiols.
Addition reactions of conjugated dienes
In this tutorial, Jay shows the possible products for an addition to a conjugated diene and how the end product can be controlled by changing the reaction conditions.
Diels-alder reaction
In this tutorial, Jay shows the mechanism, stereochemistry, and regiochemistry for the classic Diels-Alder reaction.
Molecular orbital theory
In this tutorial, Jay introduces molecular orbital (MO) theory and shows how MO theory explains the experimental observations of the Diels-Alder reaction.
Color in organic molecules
In this tutorial, Jay explains basic color theory and shows how conjugation determines the color of organic molecules. Basic knowledge of MO theory is assumed.
Naming benzene derivatives
Would a cyclohexatriene by any other name smell as sweet? In this tutorial, Sal and Jay explain how to name benzene derivatives, the sometimes sweet-smelling cyclic molecules that can be used in the synthesis of explosives and plastics.
Aromatic stability
In this tutorial, Sal and Jay explain the concept of aromatic stabilization and show how to determine if a compound or an ion exhibits aromaticity. Knowledge of MO theory is assumed.
Reactions of benzene
In this tutorial, Sal shows the mechanism of Electrophilic Aromatic Substitution and the reactions of bromination and Friedel-Crafts Acylation.
Electrophilic Aromatic Substitution
In this tutorial, Jay shows several electrophilic aromatic substitution reactions.
Directing Effects
In this tutorial, Jay shows you the directing effects of substituents on a benzene ring. Knowledge of Electrophilic Aromatic Substitution reactions is assumed.
Other Reactions and Synthesis
In this tutorial, Jay covers a few more reactions of benzene derivatives and also shows how to approach the synthesis of substituted benzene rings.
Nucleophilic Aromatic Substitution
In this tutorial, Jay shows the addition-elimination mechanism and the elimination-addition mechanism.
Nomenclature of aldehydes and ketones
In this tutorial, Sal names aldehydes and ketones.
Reactions of ketones
In this tutorial, Sal shows the mechanism of Keto-Enol Tautomerization and the Aldol reaction.
Content
Content
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
Summary
Organic Chemistry Naming Examples 1
Summary
Organic Chemistry Naming Examples 2
Summary
Organic Chemistry Naming Examples 3
Summary
Organic Chemistry Naming Examples 4
Summary
Organic Chemistry Naming Examples 5
Summary
Newman Projections
Summary
Newman Projections 2
Summary
Chair and Boat Shapes for Cyclohexane
Summary
Double Newman Diagram for Methcyclohexane
Summary
alkane and cycloalkane nomenclature I
Summary
alkane and cycloalkane nomenclature II
Summary
alkane and cycloalkane nomenclature III
Summary
bicyclic compounds
Summary
naming cubane
Summary
conformations of ethane and propane
Summary
conformations of butane
Summary
conformations of cyclohexane I: chair and boat
Summary
conformations of cyclohexane II: monosubstituted
Summary
conformations of cyclohexane III: disubstituted
Summary
conformations of cyclohexane IV: trisubstituted
Summary
Introduction to Chirality
Summary
Chiral Examples 1
Summary
Chiral Examples 2
Summary
Cahn-Ingold-Prelog System for Naming Enantiomers
Summary
R,S (Cahn-Ingold-Prelog) Naming System Example 2
Summary
chirality centers and stereoisomers
Summary
R,S system for determining absolute configuration
Summary
R,S system for cyclic compounds
Summary
optical activity I: theory
Summary
optical activity II: calculations
Summary
Stereoisomers, Enantiomers, Diastereomers, Constitutional Isomers and Meso Compounds
Summary
diastereomers
Summary
meso compounds
Summary
Naming Alkyl Halides
Summary
Sn2 Reactions
Summary
Sn1 Reactions
Summary
Steric hindrance
Summary
Sn2 Stereochemistry
Summary
Solvent Effects on Sn1 and Sn2 Reactions
Summary
Nucleophilicity (Nucleophile Strength)
Summary
Nucleophilicity vs. Basicity
Summary
E2 Reactions
Summary
E1 Reactions
Summary
Zaitsev's Rule
Summary
Comparing E2 E1 Sn2 Sn1 Reactions
Summary
E2 E1 Sn2 Sn1 Reactions Example 2
Summary
E2 E1 Sn2 Sn1 Reactions Example 3
Summary
nucleophile/electrophile and The Schwartz Rules
Summary
alkyl halide nomenclature
Summary
SN1 reaction: mechanism
Summary
SN1 reaction: stereochemistry
Summary
SN2 mechanism and stereochemistry
Summary
SN1 vs SN2: solvent effects
Summary
SN1 vs SN2: summary
Summary
E1 Elimination: mechanism
Summary
E1 Elimination: regioselectivity and stereoselectivity
Summary
carbocations and rearrangements
Summary
E1 Elimination: carbocation rearrangements
Summary
E2 Elimination: mechanism
Summary
E2 Elimination: regioselectivity
Summary
E2 Elimination: stereoselectivity
Summary
E2 Elimination: stereospecificity
Summary
E2 Elimination: substituted cyclohexanes
Summary
nucleophilicity and basicity
Summary
SN1 SN2 E1 E2 reactions: primary and tertiary alkyl halides
Summary
SN1 SN2 E1 E2 reactions: secondary alkyl halides
Summary
Naming Alkenes Examples
Summary
Cis-Trans and E-Z Naming Scheme for Alkenes
Summary
Entgegen-Zusammen Naming Scheme for Alkenes Examples
Summary
Introduction to Reaction Mechanisms
Summary
Markovnikov's Rule and Carbocations
Summary
Addition of Water (Acid-Catalyzed) Mechanism
Summary
Polymerization of Alkenes with Acid
Summary
Content
Alkene intro and stability
Summary
Alkene nomenclature
Summary
cis/trans and the E/Z system
Summary
hydrogenation
Summary
hydrohalogenation
Summary
hydration
Summary
halogenation
Summary
halohydrin formation
Summary
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
Summary
hydration of alkynes
Summary
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.
Alcohols
Naming alcohols
Alcohol Properties
Summary
alcohol nomenclature
Summary
physical properties of alcohols and preparation of alkoxides
Summary
preparation of alcohols using NaBH4
Summary
preparation of alcohols using LiAlH4
Summary
synthesis of alcohols using grignard reagents I
Summary
synthesis of alcohols using grignard reagents II
Summary
oxidation of alcohols I: mechanism and oxidation states
Summary
oxidation of alcohols II: examples
Summary
biological redox reactions
Summary
formation of nitrate esters
Summary
preparation of alkyl halides from alcohols
Summary
Ether Naming and Introduction
Summary
Ether nomenclature
Summary
Properties of ethers and crown ethers
Summary
williamson ether synthesis
Summary
acidic cleavage of ethers
Summary
Cyclic ethers and epoxide naming
Summary
nomenclature and preparation of epoxides
Summary
preparation of epoxides: stereochemistry
Summary
Ring-opening Sn2 reaction of expoxides
Summary
Sn1 and Sn2 epoxide opening discussion
Summary
ring-opening reactions of epoxides: strong nucleophiles
Summary
ring opening reactions of epoxides: acid-catalyzed
Summary
preparation of sulfides
Summary
addition reaction of conjugated dienes I: mechanism
Summary
addition reaction of conjugated dienes II: example
Summary
addition reaction of conjugated dienes III: control
Summary
diels-alder I: mechanism
Summary
diels-alder II: endo vs exo
Summary
diels-alder III: stereochemistry of dienophile
Summary
diels-alder IV: stereochemistry of diene
Summary
diels-alder V: regiochemistry
Summary
diels-alder VI: more regiochemistry
Summary
diels-alder VII: intramolecular
Summary
intro to molecular orbital (MO) theory
Summary
MO theory for butadiene
Summary
MO theory for Diels-Alder
Summary
intro to color theory
Summary
conjugation and color
Summary
color in organic molecules
Summary
Naming Benzene Derivatives Introduction
Summary
naming benzene derivatives
Summary
Aromatic Compounds and Huckel's Rule
Summary
Aromatic Stability I
The aromaticity of benzene
aromatic stability II
Summary
aromatic stability III
Summary
aromatic stability IV
Summary
aromatic stability V
Summary
Aromatic Heterocycles I
The aromaticity of pyridine and pyrimidine.
Aromatic Heterocycles II
The aromaticity of pyrrole, imidazole, and thiophene.
Resonance
Resonance in benzene and the carbonate ion
Electrophilic Aromatic Substitution
Summary
Bromination of Benzene
Bromination of benzene catalyzed by iron bromide
Friedel Crafts Acylation
Summary
Friedel Crafts Acylation Addendum
Summary
Electrophilic Aromatic Substitution Mechanism
The general reaction and mechanism of Electrophilic Aromatic Substitution
Halogenation
The halogenation of benzene
Nitration
Nitration of Benzene to form Nitrobenzene
Sulfonation
Sulfonation of benzene
Friedel-Crafts Alkylation
Summary
Friedel-Crafts Acylation
Summary
Ortho-Para Directors I
Regiochemistry
Ortho-Para Directors II
Strong Activators
Ortho-Para Directors III
Moderate and weak activation, weak deactivation
Meta Directors I
Regiochemistry
Meta Directors II
Inductive and Resonance effects
Multiple Substituents
The directing effects of substituents on a benzene ring
Birch Reduction I
The mechanism of the Birch Reduction
Birch Reduction II
The effect of electron-withdrawing and electron-donating groups
Reactions at the Benzylic Position
Free radical bromination, nucleophilic substitution, oxidation
Synthesis of Substituted Benzene Rings I
Summary
Synthesis of Substituted Benzene Rings II
Summary
Nucleophilic Aromatic Substitution I
The addition-elimination mechanism
Nucleophilic Aromatic Substitution II
The addition-elimination mechanism
Aldehyde Introduction
Summary
Ketone Naming
Summary
Keto Enol Tautomerization
Summary
Aldol Reaction
Summary