Introduction to Acid-Base Reactions – Master Organic Chemistry

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Acid Base Reactions

By James Ashenhurst

Introduction to Acid-Base Reactions

Last updated: March 21st, 2021 |

Following up on the 4 major classes of reactions you encounter in Org 1, let’s look at the first of those four: acid base reactions. The focus here is not initially to understand why things happen the way they do – that comes later. The initial focus is to be able to recognize what is happening.

Just like when you read a novel or watch a movie for the first time, your primary focus is probably just following the plot. Once you understand the plot of the movie, then you can start a deeper level of analysis with respect to the characters, setting, the meaning of the movie and so on.

Kurt Vonnegut’s great speech about plots in novels could also be applied to organic chemistry.[See below]

The “plot” of a chemical reaction is basically analyzing which bonds break and which bonds form. So let’s look the following four reactions. Before you do so it’s assumed you’ll be familiar with bond line diagrams and “hidden” hydrogens – if you need a refresher, you might find this video helpful. It’s also assumed that you know that reactants are the structures to the left of (or above) the reaction arrow, and that products are the structures to the right of the reaction arrow.

You’ll notice that they might look very different on the surface – all those different structures! – but the basic plot of each reaction is the same. We’re breaking an H-(atom) bond and forming an H-(atom) bond. At the same time we’re also connecting the two “leftover” partners to form a salt, composed of two oppositely-charged ions.



Let’s look at that last reaction in more detail. Here, we’re breaking a C-H bond and an (ionic) Na-NH2 bond, and forming an N-H bond as well as an (ionic) C-Na bond.



There are four “actors” in this reaction – as there are in every acid-base reaction – and we have names for all of them.

The reactant where the bond to H is breaking is the acid.

The reactant where the bond to H is forming is the base

The product formed when the bond to H is broken is called the conjugate base.

The product formed when the bond to H is formed is called the conjugate acid.

We can also draw the reverse of the previous reaction. Look at this carefully. We’re still breaking a bond to H and forming a bond to H, but we’ve swapped everything. We’re breaking N-H and C-Na, and forming N-Na and C-H.  It’s still an acid-base reaction. 



There’s just one thing – experiment tells us that this reaction doesn’t happen to any appreciable extent.

One way of combining both the “forward” and “reverse” reactions is to use an equilibrium arrow. If we draw it this way, another way of making the same point is that equilibrium favors the product on the right. 



Interesting! So not all acid-base reactions are equally likely. That brings up some questions.

  • Why do some acid base reactions work, but not others?
  • What factors determine the strengths of acids and bases?
  • How can we determine the equilibrium lies for an acid-base reaction?
Once you learn to recognize acid-base reactions, we can start thinking about answering these types of questions. We can also start thinking about the charges (or partial charges) on each reactant, and then start to depict where the electrons are going. 
For spoilers, look here and here.
Next Post In The Series: Introduction To Substitution Reactions

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00 General Chemistry Review
  • Gen Chem and Organic Chem: How are they different?
  • How Gen Chem Relates to Organic Chem, Pt. 1 – The Atom
  • From Gen Chem to Organic Chem, Pt. 2 – Electrons and Orbitals
  • From Gen Chem to Organic Chem, Pt. 3 – Effective Nuclear Charge
  • From Gen Chem to Organic Chem, Pt. 4 – Chemical Bonding
  • From Gen Chem to Organic Chem, Pt. 5 – Understanding Periodic Trends
  • From Gen Chem to Org Chem, Pt. 6 – Lewis Structures, A Parable
  • From Gen Chem to Org Chem, Pt. 7 – Lewis Structures
  • From Gen Chem to Org Chem, Pt. 8 – Ionic and Covalent Bonding
  • From Gen Chem to Org Chem, Pt. 9 – Acids and Bases
  • From Gen Chem to Organic Chem, Pt. 10 – Hess’ Law
  • From Gen Chem to Organic Chem, Pt. 11 – The Second Law
  • From Gen Chem to Org Chem Pt. 12 – Kinetics
  • From Gen Chem to Organic Chem, Pt. 13 – Equilibria
  • From Gen Chem to Organic Chem, Part 14: Wrapup
01 Bonding, Structure, and Resonance
  • How Concepts Build Up In Org 1 (“The Pyramid”)
  • Review of Atomic Orbitals for Organic Chemistry
  • How Do We Know Methane (CH4) Is Tetrahedral?
  • Hybrid Orbitals
  • 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
  • Partial Charges Give Clues About Electron Flow
  • 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
  • Summary Sheet – Alkane 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
  • Common Mistakes: Drawing Tetrahedral Carbons
  • Common Mistakes in Organic Chemistry: Pentavalent Carbon
  • Table of Functional Group Priorities for 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)
  • Putting the Newman into ACTION
  • 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”
  • The Ups and Downs of Cyclohexanes
  • 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
  • The 4 Major Classes of Reactions in Org 1
  • Learning New Reactions: How Do The Electrons Move?
  • How (and why) electrons flow
  • 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
  • Common Mistakes: Formal Charges Can Mislead
  • 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?
  • Leaving Groups Are Nucleophiles Acting In Reverse
  • What makes a good leaving group?
  • 3 Factors That Stabilize Carbocations
  • Three Factors that Destabilize Carbocations
  • What’s a Transition State?
  • Hammond’s Postulate
  • Grossman’s Rule
  • Draw The Ugly Version First
  • Learning Organic Chemistry Reactions: A Checklist (PDF)
  • Introduction to Addition Reactions
  • Introduction to Elimination Reactions
  • Introduction to Free Radical Substitution Reactions
  • Introduction to Oxidative Cleavage Reactions
  • Clemmensen Reduction of Ketones/Aldehydes to Alkanes
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
  • On Cats, Part 4: Enantiocats
  • On Cats, Part 6: Stereocenters
  • The Single Swap Rule
  • Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules
  • Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) – The Method of Dots
  • Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers
  • 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
  • The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate
11 SN1/SN2/E1/E2 Decision
  • 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
  • Alkyl Halide Reaction Map And Summary
  • SN1 SN2 E1 E2 Practice Problems
12 Alkene Reactions
  • E and Z Notation For Alkenes (+ Cis/Trans)
  • Alkene Stability
  • Addition Reactions: Elimination’s Opposite
  • Selective vs. Specific
  • Regioselectivity In Alkene Addition Reactions
  • Stereoselectivity In Alkene Addition Reactions: Syn vs Anti Addition
  • Markovnikov Addition Of HCl To Alkenes
  • Alkene Hydrohalogenation Mechanism And How It Explains Markovnikov’s Rule
  • Arrow Pushing and Alkene Addition Reactions
  • Addition Pattern #1: The “Carbocation Pathway”
  • Rearrangements in Alkene Addition Reactions
  • Bromination of Alkenes
  • Bromination of Alkenes: The Mechanism
  • Alkene Addition Pattern #2: The “Three-Membered Ring” Pathway
  • Hydroboration – Oxidation of Alkenes
  • Hydroboration Oxidation of Alkenes Mechanism
  • Alkene Addition Pattern #3: The “Concerted” Pathway
  • Bromonium Ion Formation: A (Minor) Arrow-Pushing Dilemma
  • A Fourth Alkene Addition Pattern – Free Radical Addition
  • Alkene Reactions: Ozonolysis
  • Summary: Three Key Families Of Alkene Reaction Mechanisms
  • Synthesis (4) – Alkene Reaction Map, Including Alkyl Halide Reactions
  • Alkene Reactions Practice Problems
13 Alkyne Reactions
  • Acetylides from Alkynes, And Substitution Reactions of Acetylides
  • Partial Reduction of Alkynes To Obtain Cis or Trans Alkenes
  • Hydroboration and Oxymercuration of Alkynes
  • Alkyne Reaction Patterns – Hydrohalogenation – Carbocation Pathway
  • Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes
  • Alkyne Reactions – The “Concerted” Pathway
  • Alkenes To Alkynes Via Halogenation And Elimination Reactions
  • Alkynes Are A Blank Canvas
  • Synthesis (5) – Reactions of Alkynes
  • Alkyne Reactions Practice Problems With Answers
  • Pinacol Rearrangement
14 Alcohols, Epoxides and Ethers
  • Alcohols (1) – Nomenclature and Properties
  • Alcohols Can Act As Acids Or Bases (And Why It Matters)
  • Alcohols (3) – Acidity and Basicity
  • The Williamson Ether Synthesis
  • Williamson Ether Synthesis: Planning
  • Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration
  • Alcohols To Ethers via Acid Catalysis
  • Cleavage Of Ethers With Acid
  • Epoxides – The Outlier Of The Ether Family
  • Opening of Epoxides With Acid
  • Epoxide Ring Opening 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
  • Calculating the oxidation state of a carbon
  • Oxidation and Reduction in Organic Chemistry
  • Oxidation Ladders
  • SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi
  • Alcohol Reactions Roadmap (PDF)
  • Alcohol Reaction Practice Problems
  • Epoxide Reaction Quizzes
  • Oxidation and Reduction Practice Quizzes
15 Organometallics
  • What’s An Organometallic?
  • Formation of Grignard and Organolithium Reagents
  • Organometallics Are Strong Bases
  • Reactions of Grignard Reagents
  • Protecting Groups In Grignard Reactions
  • Grignard Practice Problems: Synthesis (1)
  • Grignard Reactions And Synthesis (2)
  • Organocuprates (Gilman Reagents): How They’re Made
  • Gilman Reagents (Organocuprates): What They’re Used For
  • Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids!
  • The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don’t Belong In Most Introductory Organic Chemistry Courses)
  • Reaction Map: Reactions of Organometallics
  • Grignard Practice Problems
16 Spectroscopy
  • Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency)
  • Conjugation And Color (+ How Bleach Works)
  • Introduction To UV-Vis Spectroscopy
  • UV-Vis Spectroscopy: Absorbance of Carbonyls
  • UV-Vis Spectroscopy: Practice Questions
  • Bond Vibrations, Infrared Spectroscopy, and the “Ball and Spring” Model
  • Infrared Spectroscopy: A Quick Primer On Interpreting Spectra
  • IR Spectroscopy: 4 Practice Problems
  • 1H NMR: How Many Signals?
  • Homotopic, Enantiotopic, Diastereotopic
  • Diastereotopic Protons in 1H NMR Spectroscopy: Examples
  • C13 NMR – How Many Signals
  • Liquid Gold: Pheromones In Doe Urine
  • Natural Product Isolation (1) – Extraction
  • Natural Product Isolation (2) – Purification Techniques, An Overview
  • Structure Determination Case Study: Deer Tarsal Gland Pheromone
17 Dienes and MO Theory
  • What To Expect In Organic Chemistry 2
  • How Concepts Build Up In Org 2
  • Are these molecules conjugated?
  • Conjugation And Resonance In Organic Chemistry
  • Bonding And Antibonding Pi Orbitals
  • Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion
  • Pi Molecular Orbitals of Butadiene
  • Reactions of Dienes: 1,2 and 1,4 Addition
  • Thermodynamic and Kinetic Products
  • More On 1,2 and 1,4 Additions To Dienes
  • s-cis and s-trans
  • The Diels-Alder Reaction
  • Cyclic Dienes and Dienophiles in the Diels-Alder Reaction
  • Stereochemistry of the Diels-Alder Reaction
  • Exo vs Endo Products In The Diels Alder: How To Tell Them Apart
  • HOMO and LUMO In the Diels Alder Reaction
  • Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
  • Diels-Alder Reaction: Kinetic and Thermodynamic Control
  • The Retro Diels-Alder Reaction
  • Electrocyclic Ring Opening And Closure (2) – Six (or Eight) Pi Electrons
  • The Intramolecular Diels Alder Reaction
  • The Cope and Claisen Rearrangements
  • Regiochemistry In The Diels-Alder Reaction
  • Electrocyclic Reactions
  • Diels Alder Practice Problems
  • Molecular Orbital Theory Practice
18 Aromaticity
  • Introduction To Aromaticity
  • Rules For Aromaticity
  • Huckel’s Rule: What Does 4n+2 Mean?
  • “Is This Molecule Aromatic?” Some Practice Problems
  • Antiaromatic Compounds and Antiaromaticity
  • The Pi Molecular Orbitals of Benzene
  • The Pi Molecular Orbitals of Cyclobutadiene
  • Frost Circles
  • Aromaticity Practice Quizzes
19 Reactions of Aromatic Molecules
  • Electrophilic Aromatic Substitution: Introduction
  • Activating and Deactivating Groups In Electrophilic Aromatic Substitution
  • Electrophilic Aromatic Substitution – The Mechanism
  • Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution
  • Understanding Ortho, Para, and Meta Directors
  • Why are halogens ortho- para- directors?
  • Disubstituted Benzenes: The Strongest Electron-Donor “Wins”
  • Electrophilic Aromatic Substitutions (1) – Halogenation of Benzene
  • Electrophilic Aromatic Substitutions (2) – Nitration and Sulfonation
  • EAS Reactions (3) – Friedel-Crafts Acylation and Friedel-Crafts Alkylation
  • Intramolecular Friedel-Crafts Reactions
  • Nucleophilic Aromatic Substitution (NAS)
  • Nucleophilic Aromatic Substitution (2) – The Benzyne Mechanism
  • Reactions on the “Benzylic” Carbon: Bromination And Oxidation
  • The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions
  • More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger
  • Aromatic Synthesis (1) – “Order Of Operations”
  • Synthesis of Benzene Derivatives (2) – Polarity Reversal
  • Aromatic Synthesis (3) – Sulfonyl Blocking Groups
  • Birch Reduction
  • Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds
  • Aromatic Reactions and Synthesis Practice
  • Electrophilic Aromatic Substitution Practice Problems
20 Aldehydes and Ketones
  • What’s The Alpha Carbon In Carbonyl Compounds?
  • Aldehydes and Ketones: 14 Reactions With The Same Mechanism
  • Wittig Reaction
  • Imines – Properties, Formation, Reactions, and Mechanisms
  • All About Enamines
  • Hydrates, Hemiacetals, and Acetals
  • Carbonyl Chemistry: 10 Key Concepts (Part 1)
  • Carbonyls: 10 key concepts (Part 2)
  • Acid Catalysis Of Carbonyl Addition Reactions: Too Much Of A Good Thing?
  • Breaking Down Carbonyl Reaction Mechanisms: Anionic Nucleophiles (Part 1)
  • Breaking Down Carbonyl Reaction Mechanisms: Reactions of Anionic Nucleophiles (Part 2)
  • Aldehydes Ketones Reaction Practice
21 Carboxylic Acid Derivatives
  • Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles)
  • Carbonyl Mechanisms: Neutral Nucleophiles, Part 1
  • Carbonyl chemistry: Anionic versus Neutral Nucleophiles
  • Proton Transfers Can Be Tricky
  • Let’s Talk About the [1,2] Elimination
  • Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One
  • Summary Sheet #5 – 9 Key Mechanisms in Carbonyl Chemistry
  • Summary Sheet #7 – 21 Carbonyl Mechanisms on 1 page
  • How Reactions Are Like Music
  • Making Music With Mechanisms (PADPED)
  • The Magic Wand of Proton Transfer
  • The Power of Acid Catalysis
  • Amide Hydrolysis
  • Carboxylic Acid Derivatives Practice Questions
22 Enols and Enolates
  • Keto-Enol Tautomerism
  • Another awesome example of acid catalysis: Acids catalyze keto-enol tautomerism
  • Aldol Addition and Condensation Reactions
  • The Acid-Catalyzed Aldol Reaction
  • Claisen Condensation and Dieckmann Condensation
  • Decarboxylation
  • The Malonic Ester Synthesis
  • The Robinson Annulation
  • Haloform Reaction
  • The Hell–Volhard–Zelinsky Reaction
  • Enols and Enolates Practice Quizzes
23 Amines
  • The Amide Functional Group: Properties, Synthesis, and Nomenclature
  • Basicity of Amines And pKaH
  • 5 Key Basicity Trends of Amines
  • The Mesomeric Effect And Aromatic Amines
  • Nucleophilicity of Amines
  • Alkylation of Amines (Sucks!)
  • Reductive Amination
  • The Gabriel Synthesis
  • Some Reactions of Azides
  • The Hofmann Elimination
  • The Hofmann and Curtius Rearrangements
  • The Cope Elimination
  • Protecting Groups for Amines – Carbamates
  • The Strecker Synthesis of Amino Acids
  • Introduction to Peptide Synthesis
  • Reactions of Diazonium Salts: Sandmeyer and Related Reactions
  • Amine Practice Questions
24 Carbohydrates
  • D and L Notation For Sugars
  • What is Mutarotation?
  • Reducing Sugars
  • Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars
  • The Big Damn Post Of Carbohydrate-Related Chemistry Definitions
  • The Haworth Projection
  • Converting a Fischer Projection To A Haworth (And Vice Versa)
  • Reactions of Sugars: Glycosylation and Protection
  • The Ruff Degradation and Kiliani-Fischer Synthesis
  • Carbohydrates Practice
  • Amino Acid Quizzes
25 Fun and Miscellaneous
  • Organic Chemistry GIFS – Resonance Forms
  • Organic Chemistry and the New MCAT
  • A Gallery of Some Interesting Molecules From Nature
  • The Organic Chemistry Behind “The Pill”
  • Maybe they should call them, “Formal Wins” ?
  • Planning Organic Synthesis With “Reaction Maps”
  • Organic Chemistry Is Shit
  • The 8 Types of Arrows In Organic Chemistry, Explained
  • The Most Annoying Exceptions in Org 1 (Part 1)
  • The Most Annoying Exceptions in Org 1 (Part 2)
  • Reproducibility In Organic Chemistry
  • Screw Organic Chemistry, I’m Just Going To Write About Cats
  • On Cats, Part 1: Conformations and Configurations
  • On Cats, Part 2: Cat Line Diagrams
  • The Marriage May Be Bad, But the Divorce Still Costs Money
  • Why Do Organic Chemists Use Kilocalories?
  • What Holds The Nucleus Together?
  • 9 Nomenclature Conventions To Know


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