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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 ChemAlkanes and Nomenclature
Functional GroupsFree Radical Reactions
Everything I Know About Stereochemistry I Learned from CatsMore On Stereochemistry
Key Reactions of Org 1Resonance (and dipoles)
Understanding Mechanisms (How Electrons Flow)Acid Base Reactions
Substitution ReactionsRearrangement Reactions
Elimination ReactionsSN1/SN2/E1/E2 Decision
Reactions of AlkenesReactions Of Alkynes
Alcohols, Ethers, And EpoxidesOrganometallics


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


Alkanes and Nomenclature
The Many, Many Ways of Drawing ButaneHidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
The Principle of Least EffortDon’t Be Futyl, Learn The Butyls
Condensed Formulas: Deciphering The BracketsThe Ups And Downs of Cyclohexanes
Functional Group Priorities for Nomenclature8 Types Of Arrows In Organic Chemistry, Explained
Common Mistakes – Pentavalent CarbonPrimary, Secondary, Tertiary, Quaternary 
9 Weird Nomenclature Conventions To Know Organic Chemistry IUPAC Nomenclature Demystified


Functional Groups
Partial Charges3 Trends That Affect Boiling Points
Sigma Bonds Come in Six Varieties – Pi Bonds Come In OneMeet The Most Important Functional Groups
4 Intermolecular Forces And How They Affect Boiling PointsHow 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 CatsOn Cats: Conformations and Configurations
On Cats: Cat Line DiagramsOn Cats: Newman Projections
On Cats: EnantiocatsOn Cats: Enantiocats vs. Diastereocats 
On Cats: StereocentersOn Cats: The Fischer Projection
On Cats: Moe The Meso CatFare Thee Well Oh Cats of Jerusalem


More On Stereochemistry
The Single Swap RuleThe Meso Trap
How To Do Bond RotationsWhat’s A Racemic Mixture?
Homotopic, Enantiotopic, DiastereotopicSelective 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 ReactionsIntroduction to Substitution Reactions
Introduction to Addition ReactionsIntroduction to Elimination Reactions
Introduction to Rearrangement ReactionsIntroduction to Free Radical Reactions
Introduction to Oxidative Cleavage ReactionsDraw 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 ResonanceIntroduction to Resonance (2) – Curved Arrows!  
Evaluating Resonance Forms (1) – The Rule of Least ChargesEvaluating Resonance Forms (2) – Applying Electronegativity
Evaluating Resonance Forms (3) – Negative ChargesEvaluating Resonance Forms (4) – Positive Charges 
Exploring Resonance (1) – Pi DonationApplying Resonance (2) – Pi Acceptors
In Summary – ResonanceCommon Mistakes – How Not To Draw Resonance Curved Arrows
How To Apply Electronegativity and Resonance To Understand Reactivity3 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 HeadsSeven Factors That Stabilize Positive Charge 
Grossman’s RuleHammond’s Postulate
Three Classes of NucleophilesWhat’s A Transition State? 
“Nucleophile Attacks Electrophile”


Acid-Base Reactions
Introduction to Acid Base ReactionsWalkthrough of Acid-Base Reactions (1)
Walkthrough of Acid-Base Reactions (2) – BasicityAcid-Base Reactions (3) – Acidity Trends
Acid Base Reactions (4) – pKaAcid-Base Reactions (5) – How To Use a pKa Table
A Handy Rule of Thumb for Acid-Base ReactionsAcid-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 ReactionsWalkthrough 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 ReverseTwo Types of Substitution Reactions
The SN2 MechanismWhy The SN2 Is Powerful
The SN1 MechanismThe Conjugate Acid Is A Better Leaving Group
Comparing the SN1 and E1 ReactionsAll About Solvents
Steric Hindrance is Like A Fat GoalieCommon Blind Spot: Intramolecular Reactions
The Conjugate Base Is Always A Stronger Nucleophile


Rearrangement Reactions
Introduction to Rearrangement ReactionsRearrangement Reactions – Hydride Shifts
Rearrangement Reactions – Alkyl Shifts3 Factors That Stabilize Carbocations


Walkthrough of Elimination Reactions
Introduction to Elimination ReactionsWalkthrough of Elimination Reactions (1) – Introduction
Zaitsev’s RuleElimination Reactions Are Favored By Heat
Two Types of Elimination ReactionsThe E1 Mechanism
The E2 MechanismComparing the E1 and E2 Reactions
Elimination Reactions And Cyclohexane RingsBulky Bases In Elimination Reactions
Comparing The SN1 and E1 ReactionsE1 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/BaseDeciding SN1/SN2/E1/E2 (3) – The Solvent
Deciding SN1/SN2/E1/E2 (4) – The TemperatureWrapup – The Quick N’ Dirty Guide To SN1/SN2/E1/E2


Reactions of Alkenes
Addition Reactions – Elimination’s OppositeAddition Reactions – Regioselectivity
Addition Reactions – StereochemistryWhat’s Markovnikov’s Rule?
Markovnikov’s Rule (2) – Why It WorksCurved Arrows And Addition Reactions
Addition Pattern #1 – The Carbocation PathwayRearrangements in Alkene Addition Reactions
Bromination of Alkenes – How Does It Work?Bromination of Alkenes – The Mechanism
Alkene Addition Pattern #2 – The 3-Membered Ring PathwayHydroboration of Alkenes
Hydroboration of Alkenes – The MechanismAlkene Addition Pattern #3 – The “Concerted” Pathway
An Arrow-Pushing Dilemma In Alkene ReactionsFree Radical Addition To Alkenes
Ozonolysis of AlkenesSummary: Alkene Addition Pathways
Alkene Practice Problems w/ Video Solutions


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


Free Radical Reactions
Free Radical Reactions3 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 ReactionsSelectivity In Free Radical Reactions
Selectivity In Free Radical Reactions – Bromine vs. ChlorineHalogenation At Tiffany’s
Allylic BrominationAllylic Rearrangement
Free Radical Addition of HBr To AlkenesIn Summary: Free Radicals


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


Synthesis (1) – Introduction To SynthesisSynthesis (2) – Reactions of Alkanes
Synthesis (3) – Reactions of Alkyl HalidesSynthesis (4) – Reactions of Alkenes
Synthesis (5) – Reactions of AlkynesSynthesis (6) – Reactions of Alcohols


Alcohols (1) Nomenclature And PropertiesHow To Make Alcohols More Reactive
Alcohols (3) Acidity And BasicityThe Williamson Ether Synthesis
Williamson Ether Synthesis: PlanningSynthesis of Ethers (2) – Back To The Future!
Ether Synthesis Via Alcohol And AcidCleavage Of Ethers With Acid
Epoxides – The Outlier Of The Ether FamilyOpening Of Epoxides With Acid
Opening Of Epoxides With BaseMaking Alkyl Halides From Alcohols
Tosylates And MesylatesPBr3 And SOCl2
Elimination Reactions Of AlcoholsElimination Of Alcohols To Alkenes With POCl3
Alcohol Oxidation: “Strong” And “Weak” OxidantsDemystifying Alcohol Oxidations
Intramolecular Reactions Of Alcohols And EthersProtecting Groups For Alcohols
Thiols And ThioethersSynthesis (6) – Reactions Of Alcohols


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