Organic 1

by James

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 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
Elimination Reactions SN1/SN2/E1/E2 Decision
Reactions of Alkenes Reactions Of Alkynes
SN1/SN2/E1/E2 Decision (Adam Guest Post) Free Radical Reactions
Cycloalkanes Synthesis
Alcohols, Ethers, And Epoxides


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


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
Crash Course On Resonance


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
Crash Course On Alkenes


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


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 (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 (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