Illustrated Glossary of Organic Chemistry

Illustrated Glossary of Organic Chemistry
A product of the Institute for Reduction of Cognitive Entropy in Organic Chemistry

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Numbers and Symbols

Numbers and Symbols
(-) (+) 1^o 1^o carbocation 1,2-H shift 1,2-shift 1,3-H shift 1,3-shift 1,5-H shift 2^o 2^o carbocation [2+2] 2D-NMR	²H 3^o 3^o carbocation ³H [3+2] [4+2] [4+3] ¹²C ¹³C ¹⁴C α β ΔΕΝ	ΔG ΔH_f^o δ δ^- δ⁺ ε σ bond σ electron σ orbital σ* bond σ* orbital μ
A
α α,β-Unsaturated α-Amino acid α-Anomer α-Carbon α-Glycoside α-Helix α-Hydrogen α-Tocopherol Absolute configuration Abstraction Acetal Acetaldehyde Acetamide Acetate Acetic acid Acetic anhydride Acetoacetic acid Acetoacetic ester synthesis Acetone Acetonitrile Acetyl chloride Acetyl CoA Acetyl group Acetylcholine Acetylene Acetylide anion Achiral Acid anhydride Acid catalyzed Acid chloride Acid ionization constant Acid promoted Activation energy Activator Activating group AcO^- AcOR Acyclic Acyl chloride Acyl group Acylation Acylium ion Adenine Adenosine Adenosine monophosphate Adenosine triphosphate Adenylic acid Addition reaction Adriamycin Agonist Ala Alanine Alcohol Alcohol dehydrogenase Alcoholysis Aldehyde Aldohexose Aldol	Aldol condensation Aldol reaction Aldopentose Aldose Aldotriose Aliphatic Alkaloid Alkane Alkanoyl group Alkene Alkoxide Alkoxy group Alkyl group Alkyl halide Alkylammonium salt Alkylate Alkylation Alkyne Alkyne anion Alkynyl anion Allene Allose Allura Red AC Allyl carbocation Allyl group Allylic position Alpha Alpha-amino acid Alpha anomer Alpha-carbon Alpha-glycoside Alpha-helix Alpha-hydrogen Alpha, beta-unsaturated Altrose Ambident nucleophile Amide Amine Amine oxide Amino acid Amino acid residue Amino group Aminolysis Ammonia Ammonium cation Ammonium salt Amoxicillin AMP Amphotericin B Ampicillin Amu Amylopectin Amylose Anabolic steroid Analgesic Angle strain Anhydride Anhydrous	Aniline Anion Anion-cation interaction Anion-dipole interaction Anomer Anomeric carbon Anomeric effect Antagonist Anthracene Anti Anti addition Anti-inflammatory Anti-Markovnikov addition Anti-periplanar Anti-staggered Antiaromaticity Antibiotic Antibonding molecular orbital Antifungal Antimetabolite Antioxidant Aprotic solvent Aq. Aqueous Ar Arabinose Arachidic acid Arachidonic acid Arene Arenium ion Arg Arginine Aromatic-aromatic interaction Aromatic stacking Aromaticity Arrhenius equation Arrows Aryl Aryl halide Ascorbate Ascorbic acid Asn Asp Asparagine Aspartic acid Aspirin Asymmetric stretching Atomic mass unit Atomic orbital ATP Autoionization Autoxidation Axatorial Axial Aziridine Azo compound Azo coupling Azo dye Return to top
B
β β-Anomer β-Branching β-Carbon β-Elimination β-Glycoside β-Hydrogen β-Hydroxy acid β-Hydroxy aldehyde β-Hydroxy ester β-Hydroxy ketone β-Keto acid β-Keto ester β-Lactam β-Pleated sheet β-Sheet 1,3-Butadiene 9-BBN B₀ Backside attack Baeyer-Villiger oxidation Barrier to rotation Base Base catalyzed Base pair Base peak Base promoted BDE Bending mode Benzaldehyde Benzene	Benzene ring Benzo[a]pyrene Benzoic acid Benzoyl group Benzoyl peroxide Benzyl carbocation Benzyl group Benzylic position Benzyne Bergman cyclization Beta Beta-anomer Beta branching Beta-carbon Beta-elimination Beta-glycoside Beta-hydrogen Beta-hydroxy acid Beta-hydroxy aldehyde Beta-hydroxy ester Beta-hydroxy ketone Beta-keto acid Beta-keto ester Betaine Beta-lactam Beta-sheet Bicyclic Bile acid Bimolecular Biodiesel Biopolymer	Biosynthesis Boat conformation Boiling point Bond angle Bond dipole Bond dissociation energy Bond length Bond order Bond rotation Bond stretch Bond vibration Bond-line structure Bonding molecular orbital Borane Bp or BP Branched Bridged Broadband decoupling Bromination Brønsted acid Brønsted base Brønsted-Lowry acid Brønsted-Lowry base BuLi Butadiene Butane Butanol Butene Butyl group Butyllithium Butyne Return to top
C
1,3-Cyclobutadiene 1,3,5,7-Cyclooctatetraene ¹²C ¹³C ¹³C-NMR ¹⁴C C-NMR C-terminus Cahn-Ingold-Prelog rules Calicheamicin Calotte model Carbanion Carbocation Carbocation fates Carbohydrate Carbon NMR Carbonyl Carbonyl fates Carbonyl group Carboxyl group Carboxylate Carboxylate ion Carboxylic acid Carboxylic acid derivative Carcinogen Canonical form Canonical structure Carbon-12 Carbon-13 Carbon-14 Carvone Catalyst Cat. Catalytic (catalytic amount) Catalytic hydrogenation Cation Cation-anion interaction Cation-dipole interaction	Cation-pi interaction Cefaclor Cellulose Cephalosporin CFC Chain initiation Chain propagation Chain reaction Chain termination Chair conformation Chair flip ChemDraw Chemical shift Chichibabin reaction Chiral Chiral center Chlorination Chlorofluorocarbon Chloroform Chloroprene Cholesterol Chromatography Chymotrypsin Cis Claisen condensation Claisen reaction Clemmensen reduction Clinical trial Cm^-1 Coenzyme Coil Combinatorial synthesis Combustion Competitive inhibitor Complex carbohydrate Complex sugar Concerted reaction Configuration Configurational isomer	Conformation Conformational isomer Conformer Conjugate acid Conjugate base Conjugation Constitutional isomer Constructive interference Corticoid COSY COT Coupling Coupling constant Covalent bond CPK model Creatine Crystal Cumulene Cuprate Curved arrow Cyclic Cycloaddition reaction Cycloalkane Cyclobutadiene Cyclobutane Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclooctatetraene Cyclopentadiene Cyclopentadienyl anion Cyclopentadienyl cation Cyclopentane Cyclopropane Cyclopropenyl cation Cys Cysteine Cytosine Return to top
D
δ δ^- δ⁺ ΔΕΝ ΔG ΔH_f^o 1,3-Diaxial interaction d D Dalton DBE DCM Deactivating group Deactivator Decane Decarboxylation Decouple Degenerate Delocalization Deoxy Deoxyadenosine Deoxyribonucleic acid Deoxyribose Deprotection Deprotonate Deprotonization DEPT Deshielded Desolvation Destructive interference Detergent Deuterium Dewar benzene	Dextrorotatory Dextrose Diastereomer Diaxial interaction Diazo compound Diazo coupling Diazo dye Diazonium cation Diazonium salt Diazotization DIBAH DIBAL DIBAL-H Dichloromethane Dieckmann condensation Dielectric constant Diels-Alder reaction Diene Dienophile Diethyl ether Diffraction Diffraction pattern Diffractometer Dihedral angle Diisobutylaluminum hydride Dimethylallyl pyrophosphate Dimethylformamide Dimethyl sulfide Dimethylsulfoxide Diol Dipeptide Diphosphate Dipole	Dipole moment Dipole-anion interaction Dipole-cation interaction Dipole-dipole interaction Dipole-ion interaction Diradical Directing group Director Disaccharide Dispersion force Disubstituted Disulfide Disulfide bridge Diterpene Divalent Diversity oriented synthesis DMF DMSO DNA DNA alkylator DNA cutter Dodecane Double blind trial Double bond Double bond equivalent Double headed arrow Double helix Doublet Doublet of doublets Doublet of triplets Downfield Doxorubicin Drug Return to top
E
ε E E1 mechanism E1 reaction E1_cb mechanism E2 mechanism E2 reaction E_a E_act Early transition state EAS Eclipsed EDG ee EI Elec Electron cloud Electron delocalization Electron density Electron density map Electron donating group Electron impact ionization Electron releasing group Electron withdrawing group Electronegative Electronegativity Electroneutral Electrophile Electrophilic aromatic substitution	Electrophilic addition reaction Electropositive Electrostatic potential map Elimination reaction Empirical EN Enal Enamine Enantiomeric excess Enantiomer Endergonic Endothermic Energy of activation Energy profile Enol Enol form Enolate Enolization Enone Enthalpy Enthalpy of combustion Enthalpy of formation Enthalpy of hydrogenation Enzyme Enzyme-substrate docking Epibatidine Epoxide Equatorial Equial	Equilibrium constant Equivalent ERG Erythrose Ester Et Et₂O Ethane Ethanol Ethene Ether EtO^- EtOAc EtOH Ethoxide ion Ethyl acetate Ethyl alcohol Ethyl ether Ethyl group Ethylene Ethyne EWG Exact mass Excitation Excited state Exergonic Exothermic Expanded octet Return to top
F
Fat Fatty acid FDA Fingerprint region Finkelstein reaction First order coupling First order splitting Fischer esterification Fischer projection Five zone analysis	Fluorination Folic acid Formal charge Formaldehyde Fragment ion Fragmentation Free radical Freon Friedel-Crafts acylation	Friedel-Crafts alkylation Front side attack Fructofuranose Fructose Fulvene Functional group Furan Furanose Fused Return to top
G
Galactopyranose Galactose Gas chromatograph Gas chromatography Gas chromatography-mass spectrometry Gauche GC GC-MS Geminal Geometric isomer Gibbs free energy Gilman reagent	Gln Glu Glucocorticoid Glucopyranose Glucose Glutamic acid Glutamine Gly Glyceraldehyde Glycerin Glycerol Glycine	Glycolysis Glycoside Goniometer Grain alcohol Grignard reaction Grignard reagent Grob fragmentation Ground state Group Guanine Gulose Return to top
H
1,2-H shift 1,2 hydrogen shift 1,3-H shift 1,3 hydrogen shift ¹H ¹H-NMR ²H ³H H₂O₂ H₃O⁺ hν H-bond H-NMR H-rule H⁺ ("H⁺") Halide Haloalkane Haloarene Halogenoarene Halocarbon Halogen Halogenation Hammond Postulate Hard Hard water Haworth projection HBr HCl Heat of combustion Heat of formation Heat of hydrogenation	Hemiacetal Hemiketal Hemiterpene Heptane HETCOR Heteroarene Heteroaromatic Heteroaryl Heteroatom Heterocycle Heterolysis Heterolytic bond cleavage Heterolytic cleavage Hexane Hexose HF HI High-resolution mass spectrometry Highest Occupied Molecular Orbital His Histidine HMQC HOAc Hofmann degradation Hofmann elimination Hofmann's rule HOMO HOMO-LUMO gap Homolog Homolysis Homolytic bond cleavage Homolytic cleavage HOOH	Hooke's Law Hückel’s Rule Hybrid orbital Hydride Hydroboration Hydroboration-oxidation reaction Hydrocarbon Hydrobromic acid Hydrochloric acid Hydrofluoric acid Hydrogen and halogen rule Hydrogen bond Hydrogen bond acceptor Hydrogen bond donor Hydrogen bromide Hydrogen chloride Hydrogen fluoride Hydrogen iodide Hydrogen peroxide Hydrogen rule Hydroiodic acid Hydrolysis Hydronium ion Hydroperoxide Hydroperoxyl radical Hydrophilic Hydrophobic Hydrophobic effect Hydroxide ion Hydroxyl group Hydroxyl radical Hyperconjugation Return to top
I
I Idose Ile Imidazole Imine Immiscible In silico In vitro In vivo INADEQUATE Incipient carbocation IND Indole Inductive effect Infrared spectrophotometer Infrared spectroscopy Infrared spectrum Inhibitor Initiation I nitiator	Integral Integration Intercalator Intermediate Intermolecular Internal alkene Internal alkyne Intramolecular Inversion of configuration Iodination Iodoform reaction Ion Ion channel Ion pair mechanism Ion-dipole interaction Ionic bond Ionic substitution reaction Ionization Ionophore iPr	Ipso substitution IR IR spectrophotometer IR spectroscopy IR spectrum Iso Isobutylene Isobutyl group Isoelectronic Isoleucine Isomer Isomerization Isopentenyl pyrophosphate Isoprene Isoprenoid Isopropanol Isopropyl alcohol Isopropyl group Isotope IUPAC Return to top
J
J	Jones reagent
K
K_a kcal kJ Kekulé structure K_^eq	Ketal Keto form Ketone Ketohexose Ketopentose	Ketose Ketotetrose Ketotriose Kinetic control Return to top
L
l L Lactam Lactate dehydrogenase Lactone Lactose Ladenburg benzene Lanosterol Late transition state Lauric acid LDA Le Chatelier's Principle Lead compound Leaving group	Leu Leucine Levorotatory Lewis acid Lewis base Lewis dot structure Lewis structure LG Library Linear Linoleic acid Linolenic acid Lipid	Lipophilic Lipophilic vitamin Lipophobic Lithium diisopropylamide London dispersion force London force Lone pair Long range coupling Lowest Unoccupied Molecular Orbital LUMO Lys Lysine Lyxose Return to top
M
μ M M+1 M+2 m/z Magnetic anisotropy Magnetic induction Magnetic resonance imaging Maltose Major groove Major product Mannose Markovnikov addition Markovnikov's Rule Mass spectrum Mass spectrometer Mass spectrometry Mass-to-charge ratio McLafferty rearrangement mCPBA Me Mechanism Mechlorethanamine Melting point MeOH Mercaptan Meso Meso compound Mesylate Met Meta	Meta director Meta-chloroperoxybenzoic acid Metabolism Metalorganic compound Methane Methanesulfonate Methanesulfonic acid Methanol Methine group Methionine Methoxide Methoxy group Methyl Methyl alcohol Methyl carbocation Methyl carbon Methyl group Methyl sulfide Methyl sulfoxide Methyl hydrogen Methylbenzene Methylene chloride Methylene group Micelle Microscopic reversibility Mineral acid Mineralocorticoid Minor groove Minor product Miscible	Moiety Mol Molar mass Mole Molecular ion Molecular model kit Molecular recognition Molecular weight Molozonide Molecular orbital Monoatomic Monosaccharide Monosubstituted Monoterpene Monounsaturated fat Monounsaturated fatty acid Monovalent Montreal Protocol Motif Mp MRI MsO MsOH Multiplet Muriatic acid Mutagen Mutarotation MW Myoglobin Myristic acid Return to top
N
N N-bromosuccinimide N-chlorosuccinimide N-oxide N-terminus n n-BuLi n+1 Rule 4n+2 Rule N,N-dimethylformamide NaBH₄ NAD⁺ NADH NaH NAS Naked proton Name reaction Naphthalene Natta projection Natural abundance Natural product NBS NCS NDA Neighbor	Neo Neoprene Nepetalactone Newman projection Nitranion Nitration Nitric acid Nitrile Nitro group Nitrogen inversion Nitrogen rule Nitronium cation Nitrosonium cation NMR NMR spectrometer NMR spectroscopy NMR spectrum No reaction NOESY Nomenclature Nominal mass Non-first order coupling Non-first order splitting Nonane	Nonaromatic Nonbonded electron pair Nonbonded pair Noncovalent molecular force Noncovalent molecular interaction Nondecoupled Nonpolar Nonpolar solvent Nonsuperimposable Nonsuperposable Normal NR NSAID Nuc Nuclear magnetic resonance Nuclear spin flip Nucleic acid Nucleobase Nucleophile Nucleophilic acyl substitution Nucleophilic aromatic substitution Nucleophilic carbonyl substitution Nucleoside Nucleotide Return to top
O
1-Octanol O-chem ^-OAc OCATSA Ochem Octane Octane rating Octet rule Oil Oleic acid Oligosaccharide One equivalent One molecule rule Open octet Open valence electron count Optical activity Optical isomer	Optically active Optically inactive Orbital Orbital electronegativity Organic chemistry Organic synthesis Organoborane Organohalide Organometallic compound Organolithium reagent Orgo ORTEP Ortho Ortho/para director Orthoester OMs	OTf OTs Oxaphosphetaine Oxazole Oxazoline Oxidant Oxidation Oxidation reaction Oxidizing agent Oxonium ion Oxonium ion fates Oxyanion Ozone Ozone depletion Ozone hole Ozonolysis Return to top
P
π bond π orbital π* orbital p orbital PABA Palmitic acid Para Paraffin Partial pi bond PBoR Penicillin Pentane Pentapeptide Pentavalent carbon Pentet Pentose Peptide Peptide bond Peptidoglycan Peracetic acid Peracid Periplanar Peroxide Peroxide effect Peroxyacid Ph Pharmacology Phase I trial Phase II trial Phase III trial Phase IV trial Phe Phenathrene Phenol Phenyl (phenyl group) Phenylalanine Phospholipid Phospholipid bilayer Phosphate Phosphate group Phosphodiester Phosphoric acid	Photochemistry Photolysis Photon Pi bond Pi-cation interaction Pi electron Pi stacking Piperidine pK_a pK_a1 pK_a2 pK_a3 Placebo Planar Plane polarized light Polar Polar bear joke Polar covalent bond Polar solvent Polarimeter Polarimetry Polarizability Polychloroprene Polymer Polypeptide Polysaccharide Polyterpene Polyunsaturated fat Polyunsaturated fatty acid ppm Pr Primary Primary alcohol Primary alkyl halide Primary amide Primary amine Primary carbocation Primary carbon Primary hydrogen Primary structure	Prismane Pro Prodrug Product Proline Prontosil Propagation Propane Propargyl group Propargylic position Propene Propyl group Propylene Propyne Prostaglandin Protease Protection Protecting group Protein Protein Data Bank Proteinogenic amino acid Protic Protic solvent Proticity Proton Proton bus Proton NMR Proton shuttle Protonate p-Toluenesulfonate p-Toluenesulfonic acid pTsOH Pulmonary surfactant Purine Pyran Pyranose Pyridine Pyrimidine Pyrophosphate Pyrrole Pyrrolidine Return to top
Q
QSAR Quantitative structure-activity relationship Quantized	Quantum mechanics Quartet Quaternary ammonium salt	Quaternary (4^o) carbon Quaternary structure Quintet Return to top
R
R R group Racemate Racemic Racemic mixture Racemize Radical Radical cation Radical chain Radical fates Random coil Random screening Rate-determining step Rate-limiting step RCO₂R RCO₃H RCOOH RCOOR rds Reactant	Reaction coordinate Reaction mechanism Reaction product Reaction rate Reactive intermediate Reactivity-selectivity principle Receptor Redox reaction Reducing agent Reductant Reduction Reduction reaction Reflection Regiochemistry Regioselective Relaxation Relaxation time Residue Resolution Resonance	Resonance contributor Resonance contributor preference rules Resonance energy Resonance hybrid Resonance structure Retention of configuration Retinol binding protein Retroaldol reaction Retrosynthesis Ribofuranose Ribonucleic acid Ribose Ring flip Ring strain RNA RO^- ROAc ROH Rubbing alcohol Return to top
S
1,2-shift 1,3-shift σ bond σ electron σ orbital σ* bond σ* orbital S s orbital S-adenosylmethionine s-cis s-BuLi s-trans Saccharide Salicyclic acid Salt SAM Sanger's reagent SAR Saturated Sawhorse projection Saytsev's rule Saytzeff's rule Schiff base Sec Sec-butyl group Secondary Secondary alcohol Secondary alkyl halide Secondary amide Secondary amine Secondary carbocation Secondary carbon Secondary hydrogen Secondary structure Selenocysteine Ser Serine Serine protease Sesquiterpene Sesterterpene Sextet Shielded Sigma bond Sigma electron	Simple carbohydrate Simple sugar Signal Signal molecule Single bond Singlet Skeletal formula Skeletal isomer Skeletal structure S_N1 mechanism S_N2 mechanism Soap Sodium borohydride Sodium hydride Soft Solubility Solute Solvation Solvent Solvent shell Solvolysis sp orbital sp² orbital sp³ orbital Space filling model Specific rotation Spectrometer Spectrometry Spectroscopy Spectrum Spin quantum number Spin-spin coupling Spiro Splitting Spontaneous resolution Squalene Squalene oxide Squiggly line Staggered Standard amino acid Starch Starting material Stearic acid Stereocenter	Stereochemistry Stereoisomer Stereoselective Stereospecific Steric effect Steric hindrance Steric number Steric strain Steroid Stochiometry Strain Stretching frequency Structure-activity relationship Structural isomer Substituent Substituted Substitution reaction Substrate Substrate mimic Sucrose Sugar Suicide inhibitor Sulfa drug Sulfanilamide Sulfhydryl group Sulfide Sulfonamide Sulfonate Sulfonate anion Sulfonate ester Sulfonate ion Sulfonation Sulfone Sulfonic acid Sulfonyl chloride Sulfoxide Sulfuric acid Supercoiling Superimposable Superoxide Superposable Symmetric stretching Syn Syn addition Syn-periplanar Return to top
T
[TS]^‡t-BuLiTalose Tartaric acid Tautomer Tautomerization tBu tBuO^- tBuOH Teflon Teratogen Terminal alkene Terminal alkyne Termination Termolecular Terpene Terpenoid Tert Tert-butanol Tert-BuOH Tert-butoxide Tert-butyl carbocation Tert-butyl group Tertiary Tertiary alcohol Tertiary alkyl halide Tertiary amide Tertiary amine Tertiary carbocation Tertiary carbon Tertiary hydrogen Tertiary structure Tetrahedral adduct Tetrahedral carbon Tetrahedral intermediate	Tetrahydrofuran Tetramethylsilane Tetrapeptide Tetrasubstituted Tetraterpene Tetravalent Tetrose Texas carbon TfO TfOH Thalidomide Thermodynamic control THF Thiazole Thioester Thioether Thiol Thiolate Thiolester Thiophene Thr Threonine Threose Thymine TMS Toluene Toluenesulfonate Toluenesulfonic acid Torsional strain Tosylate Trans Trans fat Transamidation Transamination Transesterification	Transition state Transition state analog Transmute Transpeptidase Trehalose Triacylglyceride Triacylglycerol Tricyclic Triflate Triflic acid Trifluoroethoxide ion Trifluoromethanesulfonate Trifluoromethanesulfonic acid Trifluoromethyl group Triglyceride Trimolecular Triose Trioxolane Tripeptide Triphosphate Triple bond Triplet Triplet of doublets Trisubstituted Triterpene Tritium Trivalent Trp Tryptophan TS TsO TsOH Two-dimensional NMR Tyr Tyrosine Return to top
U
Unbranched Undecane Unimolecular	Unsaturated UN	Upfield Uracil Return to top
V
Val Valence Valence electron Valence shell Valine Van der Waals force	Van der Waals repulsion Vicinal Vinyl group Vinylic hydrogen Vinylic position Vitalism	Vitamin Vitamin C Vitamin E Volatile VSEPR Return to top
W
Walden inversion Water Watson-Crick base pair Wavenumber	Wavy line Wax Wedge Williamson ether synthesis	Wittig reaction Wolff-Kischner reduction Wood alcohol Return to top
X
X-ray crystallography X-ray diffraction	X-ray diffractometer Xylose	Xylene Return to top
Y
Ylide		Return to top
Z
Z Zaistev's Rule	Zigzag structure	Zwitterion Return to top