Organic Reactions
Alkene Reactions
- Acetylide addition [RC≡C(–)]
- Addition of Gilman reagents to enones
- Addition of Gilman to acyl halides
- Addition of Grignard reagents to esters
- Addition of Grignards to aldehydes
- Addition of Grignards to esters
- Addition of Grignards to ketones
- Addition of H3O(+)
- Addition of HBr
- Addition of HCl
- Addition of HCl, HBr, or HI (once)
- Addition of HCl, HBr, or HI (twice)
- Addition of HI
- Bromohydrin formation [Br2/H2O]
- Chlorination [Cl2]
- Cyclopropanation
- Dichlorocyclopropanation
- Dihydroxylation [KMnO4]
- Dihydroxylation [OsO4]
- Ether Formation [H+/ROH]
- Free Radical Addition of HBr
- Hydroboration-oxidation
- Hydrogenation of Alkenes
- Iodination [I2]
- Oxidative Cleavage [KMnO4]
- Oxymercuration [Hg(OAc)2/H2O]
- Oxymercuration [Hg(OAc)2/ROH]
- Ozonolysis (Oxidative workup)
- Ozonolysis (Reductive workup)
- Rearrangements (Alkyl shift)
- Rearrangements (Hydride Shift)
Alkyne Reactions
- Alkyne formation via elimination
- Deprotonation (acetylide formation)
- Hydroboration
- Hydrogenation of Alkynes
- Oxidative cleavage [KMnO4]
- Oxymercuration
- Ozonolysis
- Partial reduction [Na/NH3]
Alkanes & Free Radicals
Substitution (SN1 & SN2)
- Alcohol formation [ether cleavage]
- Alcohol formation [H2O]
- Alcohol formation [HO(–)]
- Alkanes [Gilman reagents]
- Alkyl chloride formation [HCl]
- Alkyl iodide formation [HI]
- Ammonium salt formation [RNH2]
- Azides [N3(–)]
- Ether formation [ROH]
- Nitrile formation [CN(-)]
- SN1 w/rearrangement [hydride shift]
- SN1 with rearrangement [alkyl shift]
- SN2 with alkyl halides
- SN2 with Gilman reagents
- Thiol formation [SN2]
Elimination (E1 & E2)
- Alkenes from alcohols [POCl3]
- Alkenes from alcohols [strong acid]
- E1 vs. E2
- E1 with rearrangement [hydride shift]
- E1: Alkenes from alkyl halides
- E2 Alkenes from alkyl halides
- Hofmann Elimination
Alcohol Reactions
- Conversion to alkyl bromides [PBr3]
- Conversion to alkyl chlorides [SOCl2]
- Conversion to tosylates/mesylates
- Deprotonation [alkoxide formation]
- Oxidation to aldehydes [PCC]
- Oxidation to carboxylic acids [H2CrO4 + others]
- Oxidation to ketones [PCC + others]
- Partial reduction (Lindlar)
- Protection as silyl ethers
- Protonation [onium ion formation]
Ethers & Epoxides
- Epoxidation [RCO3H]
- Epoxide formation [from alkenes]
- Epoxide formation [from halohydrins]
- Epoxide opening [acidic conditions]
- Epoxide opening [basic conditions]
- Epoxide opening [diol formation]
- Sharpless Epoxidation of alkenes
Thiols & Sulfur Compounds
Aromatic Compounds
- Aryne Formation (SNAr via arynes)
- Bromination [Br2 plus catalyst]
- Chlorination [Cl2 plus catalyst]
- Chlorohydrin formation [Cl2/H2O]
- Friedel Crafts acylation [RCOX plus catalyst]
- Friedel Crafts alkylation [R-X plus catalyst]
- Iodination [I2/catalyst]
- Nitration [HNO3/H2SO4]
- Nucleophilic Aromatic Substitution (SNAr)
- Reduction of aromatic ketones
- Reduction of nitro groups
- Side chain bromination
- Sulfonylation [SO3/H2SO4]
Aldehydes & Ketones
- Acetal formation [ROH/H+]
- Acetal hydrolysis [H3O+]
- Aldol addition reaction
- Aldol Condensation
- Alkylation of enolates
- Baeyer-Villiger Reaction
- Cannizzaro Reaction
- Clemmensen reduction to alkanes
- Conversion to ketones [Gilman reagents]
- Cyanohydrin formation [CN(–)]
- Enamine formation [R2NH]
- Enamine Hydrolysis
- Enolate formation
- Halogenation [Cl2, Br2, I2]
- Hydrate formation [H2O]
- Imine formation [RNH2]
- Keto-Enol tautomerism
- Oxidation to carboxylic acid [H2CrO4 or KMnO4]
- Oxidation to carboxylic acids [Tollens]
- Reduction of aldehydes [LiAlH4]
- Reduction of aldehydes [NaBH4]
- Reduction of ketones [LiAlH4]
- Reduction of ketones [NaBH4]
- Thioacetal formation
- Wittig reaction: alkene formation
- Wolff-Kishner: reduction to alkanes
Carboxylic Acids
- Conversion to acid chloride [SOCl2]
- Conversion to carboxylic acids [H2O]
- Decarboxylation [of β-keto acids]
- Deprotonation [carboxylate formation]
- Reduction [LiAlH4]
Carboxylic Acid Derivatives
- Amide Formation from Acid Halides
- Amide Formation Using DCC
- Beckmann Rearrangement
- Claisen condensation
- Conversion to aldehydes [LiAlH(OtBu)3]
- Conversion to amides [RNH2]
- Conversion to anhydrides [RCO2(–)]
- Conversion to esters [ROH]
- Curtius Rearrangement
- Dehydration of amides to nitriles [P2O5]
- Ester formation [RCO2(–)]
- Esterification
- Formation of Diazonium Salts
- Gabriel Synthesis of amines
- Grignard addition to aldehydes
- Hofmann rearrangement
- Hydrolysis to carboxylic acid [acidic]
- Hydrolysis to carboxylic acid [basic]
- Hydrolysis to carboxylic acids
- Reactions of Diazonium Salts
- Reduction to alcohols [LiAlH4]
- Reduction to aldehydes [DIBAL-H]
- Reduction to amines [LiAlH4]
- Reductive Amination
- Transesterification [basic conditions]
Enols, Enolates & Conjugate Addition
Dienes & Pericyclic Reactions
Organometallic Reagents
- Formation of Gilman reagents
- Formation of organolithium reagents
- Formation via Grignard and CO2
- Grignard addition to ketones
- Grignard formation [alkenyl halides]
- Grignard formation [alkyl halides]
- Haloform reaction
- Heck Reaction
- Reaction of Grignards with acid [H+]
- Reaction of Grignards with CO2
- Stille Reaction
- Suzuki Reaction
Rearrangements & Named Reactions
- Alkyl bromide formation [HBr]
- Diels–Alder reaction
- Hell-Vollhard-Zolinsky Reaction
- Kiliani Fischer Synthesis
- Malonic Ester / Acetoacetic Ester Synthesis
- Mannich Reaction
- Oxidative cleavage of vicinal diols
- Pinacol Rearrangement
- Reduction of thioacetals to alkanes [Raney Ni]
- Robinson annulation
- Stork Enamine Reaction
- Wolff Rearrangement
Biochemistry
Amino Acids & Proteins
- All 20 Amino Acids Chart (Free high-quality PDF download)
- An amino acid is drawn below
- Edman Degradation Process
- How to Purify a Protein
- How to use a pKa table
- N-terminal vs C-terminal of an Amino Acid
- Protein Sequencing Process
Enzymes & Catalysis
Hemoglobin & Myoglobin
- Bohr Effect On Oxygen Binding Behavior of Myoglobin and Hemoglobin
- Effect of BPG on Hemoglobin
- Hemoglobin: Sequential and Symmetry Model
- How to Calculate the p50 and Hill Coefficient for Myoglobin and Hemoglobin
- Structure and Function of Hemoglobin and Myoglobin
Membranes & Lipids
- Difference Between Saturated, Unsaturated, and Polyunsaturated Fatty Acids
- How to Classify Lipids
- Liposome vs. Bilayer: What Is The Difference?
- Membrane Fluidity Transition Temperature
- Membrane Proteins Explained
- Transport Across Membranes
- Types of Passive Mediated Transport
- What is a Plasmalogen?
Carbohydrates
Nucleic Acids & DNA
Chemistry Fundamentals
Molecular Structure & Properties
- How to calculate formal charge
- Intermolecular forces
- Nucleophile
- Primary, secondary, tertiary carbons
- Transition State Theory
Stereochemistry
Acids & Bases
Functional Groups
Reagent Guide
How Mechanisms Work
Spectroscopy & Analysis
NMR Spectroscopy
IR & UV-Vis Spectroscopy
Glossary (655 terms)
- [4 +2] Cycloaddition
- Absorbance
- Absorption Spectrum
- Acetal
- Acetoacetic Ester Synthesis
- Acetylide Ion
- Acid-Catalyzed Hydration
- Acidic Cleavage
- Activate
- Acyl Group
- Acyl Peroxide
- Acylium Ion
- Addition Polymers
- Addition Reactions
- Addition to pi Bond
- Adrenocortical Hormones
- Alcohol
- Aldaric Acid
- Alditol
- Aldol Addition Reaction
- Aldol Condensation
- Aldonic Acid
- Aldose
- Alkaloids
- Alkanamine
- Alkane
- Alkene
- Alkoxide
- Alkoxy Substituent
- Alkoxymercuration-Demercuration
- Alkyl Amines
- Alkyl Group
- Alkyl Halide
- Alkylation
- Alkylthio Group
- Alkynes
- Alkynide Ion
- Allylic
- Allylic Bromination
- Allylic Carbocation
- Alpha (a) Amino Acid
- Alpha (a) Position
- Amidomalonate Synthesis
- Amine
- Angle Strain
- Annulenes
- Anti Conformation
- Anti-Addition
- Anti-Coplanar
- Anti-Markovnikov Addition
- Anti-Periplanar
- Antiaromatic
- Antibonding MO
- Antioxidants
- Arenium Ion
- Aromatic
- Aryl Amine
- Asymmetric Hydrogenation
- Asymmetric Stretching
- Atomic Mass Unit (amu)
- Atomic Orbital
- Aufbau Principle
- Auto-Oxidation
- Autocatalytic
- Auxochrome
- Axial Position
- Axis of Symmetry
- Azide Synthesis
- Azo Coupling
- Azo Dyes
- Back-Side Attack
- Baeyer-Villiger Oxidation
- Base Peak
- Beer’s Law
- Bending
- Bent
- Benzylic Position
- Benzyne
- Beta (b) Anomer
- Beta (b) Pleated Sheet
- Beta (b) Position
- Beta Elimination
- Bicyclic
- Bimolecular
- Biodegradable Polymers
- Birch Reduction
- Block Copolymer
- Blocking Group
- Boat Conformation
- Bond Cleavage
- Bond Dissociation Energy
- Bond-Line Structures
- Bonding MO
- Branched Polymer
- Bredt’s Rule
- Bridgeheads
- Broadband Decoupling
- Bromohydrin
- Bromonium Ion
- Brønsted-Lowry Acid
- Brønsted-Lowry Base
- C Terminus
- Carbinolamine
- Carbocation
- Carbohydrates
- Carbonyl Group
- Carboxylic Acid Derivative
- Catalyst
- Catalytic Hydrogenation
- Cation
- Cellular Respiration
- Cephalins
- Chain Branching
- Chain Reaction
- Chain-Growth Polymer
- Chair Conformation
- Chemical Shift
- Chemically Equivalent
- Chiral
- Chirality Center
- Chlorofluorocarbons (CFCs)
- Chlorohydrin
- Chromatogram
- Chromophore
- Claisen Condensation
- Claisen Rearrangement
- Clemmensen Reduction
- Column Chromatography
- Complex Lipid
- Condensation Polymer
- Condensed Structure
- Configuration
- Conformation
- Conjugate Acid
- Conjugate Addition
- Conjugate Base
- Conjugated
- Conjugated Diene
- Conrotatory
- Conservation of Orbital Symmetry
- Constitutional Isomers
- Constructive Interference
- Continuous-Wave (CW) Spectrometer
- Cope Rearrangement
- Coplanar
- Copolymer
- Coupling (of Protons)
- Coupling (of Radicals)
- Coupling Constant
- Covalent Bond
- Crossed Aldol Reaction
- Crossed Claisen Condensation
- Crossed-Linked Polymer
- Crown Ether
- Crystallite
- Cumulated Diene
- Curved Arrows
- Cyanohydrin
- Cycloaddition Reactions
- Cycloalkane
- D-Sugar
- Dash
- Deactivate
- Debye (D)
- Decarboxylation
- Degenerate
- Degenerate Orbitals
- Degree of Substitution
- Degree of Unsaturation
- Dehydration
- Dehydrohalogenation
- Delocalization
- Delocalized
- Denaturation
- DEPT 13C NMR
- Deshielded
- Desulfurization
- Dextrorotatory
- Diagnostic Region
- Diamagnetic Anisotropy
- Diamagnetism
- Diastereomers
- Diastereotopic
- Diazonium Salt
- Diazotization
- Diborane
- Dieckmann Cyclization
- Diene
- Dienophile
- Dihedral Angle
- Dihydroxylation
- Diol
- Dipole Moment (μ)
- Dipole-Dipole Interactions
- Directed Aldol Addition
- Disaccharide
- Disrotatory
- Dissolving Metal Reduction
- Disulfide
- Disulfide Bridge
- Divalent
- Doublet
- Downfield
- E
- E1
- E1cb Mechanism
- E2
- Eclipsed Conformation
- Edman Degradation
- Eicosanoids
- Elastomers
- Electrocyclic Reaction
- Electromagnetic Spectrum
- Electron Density
- Electron Impact Ionization (EI)
- Electrophile
- Electrophilic Aromatic Substitution
- Electrophoresis
- Electrospray Ionization (ESI)
- Electrostatic Potential Maps
- Elimination
- Elimination (of Radicals)
- Elimination-Addition
- Enamine
- Enantiomer
- Enantiomeric Excess
- Enantiomerically Pure
- Enantiotopic
- Endergonic
- Endo
- Endothermic
- Energy of Activation
- Enol
- Enolate
- Enthalpy
- Entropy
- Enzymes
- Epimer
- Epoxide
- Equatorial Position
- Equilibrium
- Estrogens
- Ether
- Excited State
- Exergonic
- Exo
- Exothermic
- Fats
- Fatty Acids
- Fibers
- Fibrous Proteins
- Fingerprint Region
- First Order
- Fischer Esterification
- Fischer Projections
- Fishhook Arrow
- Flagpole Interactions
- Formal Charge
- Fourier-Transform NMR (FT-NMR)
- Fragmentation
- Free Induction Decay
- Freons
- Frequency
- Friedel-Crafts Acylation
- Friedel-Crafts Alkylation
- Frontier Orbital Theory
- Frontier Orbitals
- Frost Circles
- Functional Group
- Furanose
- Gabriel Synthesis
- Gas Chromatograph – Mass Spectrometer
- Gauche Conformation
- Gauche Interaction
- Geminal
- Gibbs Free Energy
- Gilman Reagent
- Glass Transition Temperature (Tg)
- Globular Proteins
- Glycoside
- Graft Copolymer
- Grignard Reagent
- Haloalkane
- Haloform Reaction
- Halogen Abstraction
- Halogenation
- Halohydrin Formation
- Hammond Postulate
- Haworth Projection
- Heat of Combustion
- Heat of Reaction
- Hell-Volhard-Zelinsky Reaction
- Hemiacetal
- Henderson-Hasselbalch Equation
- Heterocycle
- Heterogeneous Catalyst
- Heterolytic Bond Cleavage
- High-Resolution Mass Spectrometry
- Hofmann Elimination
- Hofmann Product
- HOMO
- Homogeneous Catalysts
- Homolitic Bond Cleavage
- Homopolymer
- Homotopic
- Hund’s Rule
- Hydrate
- Hydration
- Hydrazone
- Hydride Shift
- Hydroboration-Oxidation
- Hydrochlorofluorocarbons, (HCFCs)
- Hydrocracking
- Hydrofluorocarbons (HFCs)
- Hydrogen Abstraction
- Hydrogen Bonding
- Hydrogen Deficiency Index (HDI)
- Hydrohalogenation
- Hydrolysis
- Hydroperoxide
- Hydrophilic
- Hydrophobic
- Hydroxyl Group
- Hyperconjugation
- Hückel’s Rule
- Imidazole
- Imine
- Induction
- Initiation
- Integration
- Intermediate
- Intermolecular Forces
- Internal Alkyne
- Inversion of Configuration
- Ionic Bond
- Ionic Reaction
- Isoelectric Point (pI)
- Isolated Diene
- Isoprene
- Isotactic
- IUPAC
- J Value
- Ka
- Keq
- Keto-Enol Tautomerization
- Ketose
- Kiliani-Fischer Synthesis
- Kinetic Control
- Kinetics
- L Amino Acid
- L sugar
- Labile
- Lactone
- Lambda Max (lmax)
- Leaving Group
- Lecithins
- Leveling Effect
- Levorotatory
- Lewis Acid
- Lewis Base
- Lewis Structures
- Linear Polymer
- Lipid
- Lipid Bilayer
- Lithium Dialkyl Cuprate
- Living Polymer
- Localized Lone Pair
- Locant
- London Dispersion Forces
- Lone Pair
- Loss of a Leaving Group
- LUMO
- Magnetic Moment
- Malonic Ester Synthesis
- Markovnikov Addition
- Mass Spectrometer
- Mass Spectrometry
- Mass Spectrum
- Mass-to-Charge Ratio(m/z)
- Meisenheimer Complex
- Melt Transition Temperature (Tm)
- Mercapto Group
- Mercurinium Ion
- Merrifield Synthesis
- Meso Compound
- Meta
- Meta Director
- Methine Group
- Methyl Shift
- Methylene Group
- Micelle
- Michael Acceptor
- Michael Donor
- Michael Reaction
- Migratory Aptitude
- Miscible
- Mixed Aldol Reaction
- Moderate Activators
- Moderate Deactivators
- Molar Absorptivity
- Molecular Dipole Moment
- Molecular Ion
- Molecular Orbital (MO) Theory
- Molecular Orbitals
- Monosaccharides
- Monovalent
- Multiplet
- Multiplicity
- Mutarotation
- N Terminus
- N+1 Rule
- N-Bromosuccinimide
- N-Glycoside
- N-Nitrosamine
- Newman Projection
- Nitration
- Nitrogen Rule
- Nitronium Ion
- Nitrosonium Ion
- Nitrous Acid
- Node
- Nomenclature
- Nonaromatic
- Norbornane
- Nuclear Magnetic Resonance (NMR)
- Nucleophile
- Nucleophilic Acyl Substitution
- Nucleophilic Aromatic Substitution
- Nucleophilic Attack
- Nucleosides
- Nucleotides
- Observed Rotation
- Octet Rule
- Off-Resonance Decoupling
- Oils
- Oligomers
- Optically Active
- Optically Inactive
- Optically Pure
- Organohalide
- Ortho
- Ortho-Para Director
- Oxaphosphetane
- Oxidation
- Oxidation State
- Oxime
- Oxirane
- Oxonium Ion
- Oxymercuration-Demercuration
- Ozonolysis
- Para
- Parent Ion
- Partially Condensed Structures
- Pauli Exclusion Principle
- Peptidases
- Peptide
- Peptide Bond
- Pericylic Reactions
- Periplanar
- Peroxides
- Phenolate
- Phenoxide
- Phenyl Group
- Phosphatidic Acid
- Phosphoglycerides
- Phospholipids
- Photochemical Reaction
- Photon
- Physiological pH
- Pi (p) Bond
- Plane of Symmetry
- Plane-Polarized Light
- Plasticizers
- Polar Aprotic Solvent
- Polar Covalent Bond
- Polar Reaction
- Polarimeter
- Polarizability
- Polarization
- Polycarbonates
- Polycyclic Aromatic Hydrocarbons (PAHs)
- Polyether
- Polynucleotide
- Polysaccharides
- Polyurethanes
- Polyvinyl Chloride, (PVC)
- Primary
- Primary Alkyl Halide
- Primary Structure
- Progestins
- Propagation
- Prostaglandins
- Prosthetic Group
- Protecting Group
- Proteins
- Protic Solvent
- Proton Transfer
- Pyranose Ring
- Pyrimidine
- Quantum Mechanics
- Quartet
- Quaternary Ammonium Salt
- Quaternary Structure
- Quintet
- R
- Racemic Mixture
- Radical
- Radical Anion
- Radical Inhibitor
- Radical Initiator
- Random Copolymer
- Rate Equation
- Rate-Determining Step
- Reaction Mechanism
- Rearrangement
- Reducing Agent
- Reducing Sugar
- Reduction
- Reductive Amination
- Regiochemistry
- Regioselective
- Replacement Test
- Resolution
- Resolving Agents
- Resonance
- Resonance Hybrid
- Resonance Stabilization
- Resonance Structures
- Retention of Configuration
- Retention Time
- Retro Diels-Alder Reaction
- Retro-Aldol Reaction
- Retrosynthetic Analysis
- Ring Flip
- Robinson Annulation
- S
- s-Cis
- S-Trans
- Sandmeyer Reactions
- Saponification
- Saturated
- Saturated Hydrocarbon
- Schiemann Reaction
- Second Order
- Secondary
- Secondary Alkyl Halide
- Secondary Structure
- Sharpless Asymmetric Epoxidation
- Shielded
- Sigma (s) Bond
- Sigma Complex
- Sigmatropic Rearrangements
- Simple Lipid
- Singlet
- SN1
- SN2
- Sodium Cyanoborohydride
- Soluble
- Solvent Extraction
- Solvolysis
- Sp-Hybridized Orbitals
- Sp2-Hybridized Orbitals
- Sp3-Hybridized Orbitals
- Specific Rotation
- Spectroscopy
- Spin-Spin Splitting
- Spontaneous
- Staggered Conformation
- Standard Atomic Weight
- Step-Growth Polymers
- Stereoisomers
- Stereoselective
- Stereospecific
- Steric Number
- Sterically Hindered
- Steroids
- Stork Enamine Synthesis
- Strecker Synthesis
- Stretching
- Strong Activators
- Strong Deactivators
- Structural Proteins
- Substituents
- Substitution Reactions
- Substrate
- Sulfide
- Sulfonate Ions
- Sulfonation
- Sulfone
- Sulfoxide
- Superimposable
- Symmetric Stretching
- Symmetrical Ether
- Symmetry Allowed
- Symmetry Forbidden
- Syn Addition
- Syn-Coplanar
- Syndiotactic
- Systematic Name
- Tautomers
- Terminal Alkynes
- Termination
- Termolecular
- Terpenes
- Tertiary
- Tertiary Alkyl Halide
- Tertiary Structure
- Tetrahedral
- Tetrahedral Intermediate
- Tetravalent
- Thermodynamic Control
- Thermodynamics
- Thermoplastics
- Thermosetting Resins
- Thioacetal
- Thiolate
- Thiols
- Third Order
- Three-Center, Two Electron Bonds
- Torsional Angle
- Torsional Strain
- Tosylate
- Transition State
- Transport Protein
- Triglyceride
- Trigonal Planar
- Trigonal Pyramidal
- Triplet
- Trivalent
- Twist Boat
- Unimolecular
- Unsaturated
- Unsymmetrical Ether
- Upfield
- Valence Bond Theory
- Vibrational Excitation
- Vicinal
- Vinylic
- Vinylic Carbocation
- VSEPR Theory
- Wavelength
- Wavenumber
- Waxes
- Weak Activators
- Weak Deactivators
- Wedge
- Williamson Ether Synthesis
- Wittig Reaction
- Wittig Reagent
- Wohl Degradation
- Woodward-Fieser Rules
- Ylide
- Z
- Zaitsev Product
- Zwitterion