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Organic 1

Here’s an index of posts for relevant topics in Organic Chemistry 1 (first-semester organic chemistry).
[Hint – searching for something specific? Try CNTRL-F]

From Gen Chem to Organic Chem	Alkanes and Nomenclature
Functional Groups	Free Radical Reactions
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
Elimination Reactions	SN1/SN2/E1/E2 Decision
Reactions of Alkenes	Reactions Of Alkynes
Cycloalkanes	Synthesis
Alcohols, Ethers, And Epoxides	Organometallics

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	Organic Chemistry IUPAC Nomenclature Demystified

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

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	Chiral Allenes and Chiral Axes
Stereochemistry Exam Problems w/ Video Solutions

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
Solved Resonance Problems w/ Video Solutions

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
Alkene Practice Problems w/ Video Solutions

Reactions of Alkynes
The 2 Most Important Reactions of Alkynes	Partial Reduction Of Alkynes
Hydroboration and Oxymercuration of Alkynes	Alkyne Reaction Patterns – The Carbocation Pathway
Alkyne Reaction Patterns – The 3 Membered Ring Pathway	Alkyne Reaction Patterns – The Concerted Pathway
Alkynes via Elimination Reactions	Alkynes Are A Blank Canvas
Alkyne Practice Problems w/ Video Solutions

Free Radical Reactions
Free Radical Reactions	3 Factors That Stabilize Free Radicals
What Factors Destabilize Free Radicals?	Bond Strengths And Radical Stability
Radical Reactions – Why Is “Heat” Or “Light” Required?	Initiation, Propagation, Termination
Isomers From Free Radical Reactions	Selectivity In Free Radical Reactions
Selectivity In Free Radical Reactions – Bromine vs. Chlorine	Halogenation At Tiffany’s
Allylic Bromination	Allylic Rearrangement
Free Radical Addition of HBr To Alkenes	In Summary: Free Radicals

Introduction to Cycloalkanes
Introduction	Dashes And Wedges
Ring Strain (and How To Calculate It)	Ring Strain in Cyclopropane and Cyclobutane
Ring Strain in Cyclopentane and Cyclohexane	An Aerial Tour of The Cyclohexane Chair
How To Draw A Cyclohexane Chair	The Cyclohexane Chair Flip
The Cyclohexane Chair Flip Energy Diagram	Equatorial vs. Axial
Substituted Cyclohexanes (A-Values)	Which Chair Is Of Lower Energy?
Fused Rings	Bridged Bicyclic Rings
Bredt’s Rule (and wrap-up of cycloalkanes)

Synthesis
Synthesis (1) – Introduction To Synthesis	Synthesis (2) – Reactions of Alkanes
Synthesis (3) – Reactions of Alkyl Halides	Synthesis (4) – Reactions of Alkenes
Synthesis (5) – Reactions of Alkynes	Synthesis (6) – Reactions of Alcohols

Alcohols
Alcohols (1) Nomenclature And Properties	How To Make Alcohols More Reactive
Alcohols (3) Acidity And Basicity	The Williamson Ether Synthesis
Williamson Ether Synthesis: Planning	Synthesis of Ethers (2) – Back To The Future!
Ether Synthesis Via Alcohol And Acid	Cleavage Of Ethers With Acid
Epoxides – The Outlier Of The Ether Family	Opening Of Epoxides With Acid
Opening Of Epoxides With Base	Making Alkyl Halides From Alcohols
Tosylates And Mesylates	PBr₃ And SOCl₂
Elimination Reactions Of Alcohols	Elimination Of Alcohols To Alkenes With POCl₃
Alcohol Oxidation: “Strong” And “Weak” Oxidants	Demystifying Alcohol Oxidations
Intramolecular Reactions Of Alcohols And Ethers	Protecting Groups For Alcohols
Thiols And Thioethers	Synthesis (6) – Reactions Of Alcohols

Organometallics
What’s an Organometallic?	Synthesis of Grignard and Organolithium Reagents
Organometallics Are Strong Bases	Reactions of Grignard Reagents
Protecting Groups and Grignard Reagents	Grignard Reagents In Synthesis (1)
Grignard Reagents In Synthesis (2)	Gilman Reagents (Organocuprates): How They’re Made
Gilman Reagents: What They’re Used For	Heck, Suzuki, and Olefin Metathesis
Reaction Map: Reactions of Organometallics