Organic 1

Here’s an index of posts for relevant topics in Organic Chemistry 1 (first-semester organic chemistry).

From Gen Chem to Organic Chem	Alkanes and Nomenclature
Functional Groups	Khan Academy for Organic Chemistry
Everything I Know About Stereochemistry I Learned from Cats	More On Stereochemistry
Key Reactions of Org 1	Resonance (and dipoles)
Understanding Mechanisms (How Electrons Flow)	Acid Base Reactions
Substitution Reactions	Rearrangement Reactions
Walkthrough of Elimination Reactions	SN1/SN2/E1/E2 Decision
Reactions of Allkenes

 

From Gen Chem to Organic Chem
General Chem and Organic Chem: How are they Different?	Part 1: The Atom
Part 2: Electrons and Orbitals	Part 3: Effective Nuclear Charge
Part 4: Chemical Bonding	Part 5: Understanding Periodic Trends
Part 6: Lewis Structures, A Fable	Part 7: Lewis Structures
Part 8: Ionic and Covalent Bonding	Part 9: Acids and Bases
Part 10: Hess’ Law	Part 11: The Second Law of Thermodynamics
Part 12: Chemical Kinetics	Part 13: Equilibria
Part 14: Wrapup

 

Alkanes and Nomenclature
The Many, Many Ways of Drawing Butane	Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
The Principle of Least Effort	Don’t Be Futyl, Learn The Butyls
Condensed Formulas: Deciphering The Brackets	The Ups And Downs of Cyclohexanes
Functional Group Priorities for Nomenclature	8 Types Of Arrows In Organic Chemistry, Explained
Common Mistakes – Pentavalent Carbon	Primary, Secondary, Tertiary, Quaternary
9 Weird Nomenclature Conventions To Know

 

Functional Groups
Partial Charges	3 Trends That Affect Boiling Points
Sigma Bonds Come in Six Varieties – Pi Bonds Come In One	Meet The Most Important Functional Groups
4 Intermolecular Forces And How They Affect Boiling Points	How To Calculate Formal Charge
How Symmetry Is Related To Melting Points and Boiling Points

 

Khan Academy for Organic Chemistry
Part 1 – Videos 1-12 (mostly alkane nomenclature)	Part 2 – Videos 13-26 (mostly conformations)
Part 3 – Videos 27-37 (mostly substitution reactions)	Part 4 – Videos 38-51 (mostly substitution and elimination)
Part 5 – Videos 52-64 (mostly aldehydes/ketones)	Part 6 – Videos 65-73 (carboxylic acids)
In Summary: How Useful Are Khan Academy Videos?

 

Everything I Know About Stereochemistry I Learned From Cats
Screw Organic Chemistry, I’m Just Going to Write About Cats	On Cats: Conformations and Configurations
On Cats: Cat Line Diagrams	On Cats: Newman Projections
On Cats: Enantiocats	On Cats: Enantiocats vs. Diastereocats
On Cats: Stereocenters	On Cats: The Fischer Projection
On Cats: Moe The Meso Cat	Fare Thee Well Oh Cats of Jerusalem

 

More On Stereochemistry
The Single Swap Rule	The Meso Trap
How To Do Bond Rotations	What’s A Racemic Mixture?
Homotopic, Enantiotopic, Diastereotopic	Selective Versus Specific
Ephedrine and Pseudoephedrine

 

Key Reactions of Org 1
The Most Important Question To Ask When Learning A New Reaction	4 Major Classes of Reactions In Org 1
Introduction to Acid Base Reactions	Introduction to Substitution Reactions
Introduction to Addition Reactions	Introduction to Elimination Reactions
Introduction to Rearrangement Reactions	Introduction to Free Radical Reactions
Introduction to Oxidative Cleavage Reactions	Draw The Ugly Version First

 

Understanding Where Electrons Are – Dipoles And Resonance
The Second Most Important Question To Ask When Learning A New Reaction	Watch Out! Formal Charge Can Lie
Introduction to Resonance	Introduction to Resonance (2) – Curved Arrows!
Evaluating Resonance Forms (1) – The Rule of Least Charges	Evaluating Resonance Forms (2) – Applying Electronegativity
Evaluating Resonance Forms (3) – Negative Charges	Evaluating Resonance Forms (4) – Positive Charges
Exploring Resonance (1) – Pi Donation	Applying Resonance (2) – Pi Acceptors
In Summary – Resonance	Common Mistakes – How Not To Draw Resonance Curved Arrows
How To Apply Electronegativity and Resonance To Understand Reactivity	3 Factors That Stabilize Carbocations
3 Factors that Destabilize Carbocations

 

Understanding How Reactions Work – Electron Flow
How (and why) Electrons Flow	The Third Most Important Question To Ask When Learning A New Reaction
Common Mistakes – Formal Charge Can Mislead	Seven Factors That Stabilize Negative Charge (and why it matters)
Curved Arrows – Initial Tails and Final Heads	Seven Factors That Stabilize Positive Charge
Grossman’s Rule	Hammond’s Postulate
Three Classes of Nucleophiles	What’s A Transition State?
“Nucleophile Attacks Electrophile”

 

Acid-Base Reactions
Introduction to Acid Base Reactions	Walkthrough of Acid-Base Reactions (1)
Walkthrough of Acid-Base Reactions (2) – Basicity	Acid-Base Reactions (3) – Acidity Trends
Acid Base Reactions (4) – pKa	Acid-Base Reactions (5) – How To Use a pKa Table
A Handy Rule of Thumb for Acid-Base Reactions	Acid-Base Reactions Are Fast
Acid-Base Reactions – What’s the Point?	5 Key Factors That Influence Acidity
The pKa Table Is Your Friend	Putting Acidity In Perspective

 

Substitution Reactions
Introduction to Substitution Reactions	Walkthrough of Substitution Reactions (1)
Nucleophiles And Electrophiles	Nucleophilicity Versus Basicity
What Makes A Good Nucleophile?	What Makes A Good Leaving Group?
Leaving Groups Are Nucleophiles Acting In Reverse	Two Types of Substitution Reactions
The SN2 Mechanism	Why The SN2 Is Powerful
The SN1 Mechanism	The Conjugate Acid Is A Better Leaving Group
Comparing the SN1 and E1 Reactions	All About Solvents
Steric Hindrance is Like A Fat Goalie	Common Blind Spot: Intramolecular Reactions
The Conjugate Base Is Always A Stronger Nucleophile

 

Rearrangement Reactions
Introduction to Rearrangement Reactions	Rearrangement Reactions – Hydride Shifts
Rearrangement Reactions – Alkyl Shifts	3 Factors That Stabilize Carbocations

 

Walkthrough of Elimination Reactions
Introduction to Elimination Reactions	Walkthrough of Elimination Reactions (1) – Introduction
Zaitsev’s Rule	Elimination Reactions Are Favored By Heat
Two Types of Elimination Reactions	The E1 Mechanism
The E2 Mechanism	Comparing the E1 and E2 Reactions
Elimination Reactions And Cyclohexane Rings	Bulky Bases In Elimination Reactions
Comparing The SN1 and E1 Reactions	E1 Reactions With Rearrangements

 

Walkthrough of SN1/SN2/E1/E2 Decision
Trapped In SN1/SN2/E1/E2 Hell? Some Resources	Deciding SN1/SN2/E1/E2 (1) – The Substrate
Deciding SN1/SN2/E1/E2 (2) – The Nucleophile/Base	Deciding SN1/SN2/E1/E2 (3) – The Solvent
Deciding SN1/SN2/E1/E2 (4) – The Temperature	Wrapup – The Quick N’ Dirty Guide To SN1/SN2/E1/E2

 

Reactions of Alkenes
Addition Reactions – Elimination’s Opposite	Addition Reactions – Regioselectivity
Addition Reactions – Stereochemistry	What’s Markovnikov’s Rule?
Markovnikov’s Rule (2) – Why It Works	Curved Arrows And Addition Reactions
Addition Pattern #1 – The Carbocation Pathway	Rearrangements in Alkene Addition Reactions
Bromination of Alkenes – How Does It Work?	Bromination of Alkenes – The Mechanism
Alkene Addition Pattern #2 – The 3-Membered Ring Pathway	Hydroboration of Alkenes
Hydroboration of Alkenes – The Mechanism	Alkene Addition Pattern #3 – The “Concerted” Pathway
An Arrow-Pushing Dilemma In Alkene Reactions	Free Radical Addition To Alkenes
Ozonolysis of Alkenes	Summary: Alkene Addition Pathways