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Master Organic Chemistry Study Guides Reactions and Mechanisms Quizzes Free Stuff MOC Membership Tutoring Search Type and Press enter” to Search Searching... Tutoring Login Ace Your Next Organic Chemistry Exam. With the MOC Membership ORG 1 SPEC ORG 2 REAGENTS REACTIONS Free samples 1500+ Real-World exam quizzes 180+ Reactions and Mechanisms 200+ Downloadable Flashcards Organic Chemistry is Awesome Over 400+ blog posts to guide you through introductory Organic Chemistry, organized by subject. 00 General Chemistry Review Lewis Structures Ionic and Covalent Bonding Chemical Kinetics Chemical Equilibria Valence Electrons of the First Row Elements How Concepts Build Up In Org 1 ("The Pyramid") 01 Bonding, Structure, and Resonance How Do We Know Methane (CH4) Is Tetrahedral? Hybrid Orbitals and Hybridization How To Determine Hybridization: A Shortcut Orbital Hybridization And Bond Strengths Sigma bonds come in six varieties: Pi bonds come in one A Key Skill: How to Calculate Formal Charge The Four Intermolecular Forces and How They Affect Boiling Points 3 Trends That Affect Boiling Points How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge) Introduction to Resonance How To Use Curved Arrows To Interchange Resonance Forms Evaluating Resonance Forms (1) - The Rule of Least Charges How To Find The Best Resonance Structure By Applying Electronegativity Evaluating Resonance Structures With Negative Charges Evaluating Resonance Structures With Positive Charge Exploring Resonance: Pi-Donation Exploring Resonance: Pi-acceptors In Summary: Evaluating Resonance Structures Drawing Resonance Structures: 3 Common Mistakes To Avoid How to apply electronegativity and resonance to understand reactivity Bond Hybridization Practice Structure and Bonding Practice Quizzes Resonance Structures Practice 02 Acid Base Reactions Introduction to Acid-Base Reactions Acid Base Reactions In Organic Chemistry The Stronger The Acid, The Weaker The Conjugate Base Walkthrough of Acid-Base Reactions (3) - Acidity Trends Five Key Factors That Influence Acidity Acid-Base Reactions: Introducing Ka and pKa How to Use a pKa Table The pKa Table Is Your Friend A Handy Rule of Thumb for Acid-Base Reactions Acid Base Reactions Are Fast pKa Values Span 60 Orders Of Magnitude How Protonation and Deprotonation Affect Reactivity Acid Base Practice Problems 03 Alkanes and Nomenclature Meet the (Most Important) Functional Groups Condensed Formulas: Deciphering What the Brackets Mean Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions Don’t Be Futyl, Learn The Butyls Primary, Secondary, Tertiary, Quaternary In Organic Chemistry Branching, and Its Affect On Melting and Boiling Points The Many, Many Ways of Drawing Butane Wedge And Dash Convention For Tetrahedral Carbon Common Mistakes in Organic Chemistry: Pentavalent Carbon Table of Functional Group Priorities for Nomenclature Summary Sheet - Alkane Nomenclature Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach Boiling Point Quizzes Organic Chemistry Nomenclature Quizzes 04 Conformations and Cycloalkanes Staggered vs Eclipsed Conformations of Ethane Conformational Isomers of Propane Newman Projection of Butane (and Gauche Conformation) Introduction to Cycloalkanes (1) Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes Calculation of Ring Strain In Cycloalkanes Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane Cyclohexane Conformations Cyclohexane Chair Conformation: An Aerial Tour How To Draw The Cyclohexane Chair Conformation The Cyclohexane Chair Flip The Cyclohexane Chair Flip - Energy Diagram Substituted Cyclohexanes - Axial vs Equatorial Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values" Cyclohexane Chair Conformation Stability: Which One Is Lower Energy? Fused Rings - Cis-Decalin and Trans-Decalin Naming Bicyclic Compounds - Fused, Bridged, and Spiro Bredt’s Rule (And Summary of Cycloalkanes) Newman Projection Practice Cycloalkanes Practice Problems 05 A Primer On Organic Reactions The Most Important Question To Ask When Learning a New Reaction Learning New Reactions: How Do The Electrons Move? The Third Most Important Question to Ask When Learning A New Reaction 7 Factors that stabilize negative charge in organic chemistry 7 Factors That Stabilize Positive Charge in Organic Chemistry Nucleophiles and Electrophiles Curved Arrows (for reactions) Curved Arrows (2): Initial Tails and Final Heads Nucleophilicity vs. Basicity The Three Classes of Nucleophiles What Makes A Good Nucleophile? What makes a good leaving group? 3 Factors That Stabilize Carbocations Equilibrium and Energy Relationships What’s a Transition State? Hammond’s Postulate Learning Organic Chemistry Reactions: A Checklist (PDF) Introduction to Free Radical Substitution Reactions Introduction to Oxidative Cleavage Reactions 06 Free Radical Reactions Bond Dissociation Energies = Homolytic Cleavage Free Radical Reactions 3 Factors That Stabilize Free Radicals What Factors Destabilize Free Radicals? Bond Strengths And Radical Stability Free Radical Initiation: Why Is "Light" Or "Heat" Required? Initiation, Propagation, Termination Monochlorination Products Of Propane, Pentane, And Other Alkanes Selectivity In Free Radical Reactions Selectivity in Free Radical Reactions: Bromination vs. Chlorination Halogenation At Tiffany’s Allylic Bromination Bonus Topic: Allylic Rearrangements In Summary: Free Radicals Synthesis (2) - Reactions of Alkanes Free Radicals Practice Quizzes 07 Stereochemistry and Chirality Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers How To Draw The Enantiomer Of A Chiral Molecule How To Draw A Bond Rotation Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots Enantiomers vs Diastereomers vs The Same? Two Methods For Solving Problems Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams) How To Determine R and S Configurations On A Fischer Projection The Meso Trap Optical Rotation, Optical Activity, and Specific Rotation Optical Purity and Enantiomeric Excess What’s a Racemic Mixture? Chiral Allenes And Chiral Axes Stereochemistry Practice Problems and Quizzes 08 Substitution Reactions Introduction to Nucleophilic Substitution Reactions Walkthrough of Substitution Reactions (1) - Introduction Two Types of Nucleophilic Substitution Reactions The SN2 Mechanism Why the SN2 Reaction Is Powerful The SN1 Mechanism The Conjugate Acid Is A Better Leaving Group Comparing the SN1 and SN2 Reactions Polar Protic? Polar Aprotic? Nonpolar? All About Solvents Steric Hindrance is Like a Fat Goalie Common Blind Spot: Intramolecular Reactions The Conjugate Base is Always a Stronger Nucleophile Substitution Practice - SN1 Substitution Practice - SN2 09 Elimination Reactions Elimination Reactions (1): Introduction And The Key Pattern Elimination Reactions (2): The Zaitsev Rule Elimination Reactions Are Favored By Heat Two Elimination Reaction Patterns The E1 Reaction The E2 Mechanism E1 vs E2: Comparing the E1 and E2 Reactions Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings Bulky Bases in Elimination Reactions Comparing the E1 vs SN1 Reactions Elimination (E1) Reactions With Rearrangements E1cB - Elimination (Unimolecular) Conjugate Base Elimination (E1) Practice Problems And Solutions Elimination (E2) Practice Problems and Solutions 10 Rearrangements Introduction to Rearrangement Reactions Rearrangement Reactions (1) - Hydride Shifts Carbocation Rearrangement Reactions (2) - Alkyl Shifts Pinacol Rearrangement The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate 11 SN1/SN2/E1/E2 Decision Identifying Where Substitution and Elimination Reactions Happen Deciding SN1/SN2/E1/E2 (1) - The Substrate Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base SN1 vs E1 and SN2 vs E2 : The...