Illustrated Glossary of Organic Chemistry

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

"The beginning of wisdom is to call things by their proper name." ― Confucius

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Statement of Purpose

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IUPAC Compendium of Chemical Terminology - the Gold Book

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The glossary currently includes

2196

terms.

Newest entries: Substitution nucleophilic bimolecular, substitution nucleophilic 2^nd order, substitution nucleophilic unimolecular, substitution nucleophilic 1^st order, 1^st order (kinetics), first order (kinetics), 2^nd order (kinetics), second order (kinetics)

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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 ¹H ¹H-NMR 1^st order (kinetics) 2^o 2^o carbocation [2+2] 2D-NMR ²H 2^nd order (kinetics) 3^o	3^o carbocation ³H [3+2] 3,3-shift 4^o [4+2] [4+3] ¹²C ¹³C ¹⁴C α β ΔE ΔΕΝ ΔG ΔG⁺⁺ ΔH ΔH_f^o	ΔS δ δ^- δ⁺ ε λ λ_max π bond π electron π orbital π* orbital σ bond σ electron σ orbital σ* bond σ* orbital μ
A
1,4-Addition α α,β-Unsaturated α,β Unsaturated ketone α-Amino acid α-Anomer α-Carbon α-Glycoside α-Helix α-Hydrogen α-Hydroxy ketone α-Tocopherol Absolute configuration Abstraction Acetal Acetaldehyde Acetamide Acetate Acetate ion Acetic acid Acetic anhydride Acetoacetic acid Acetoacetic ester synthesis Acetone Acetonitrile Acetophenone Acetyl chloride Acetyl-CoA Acetyl group Acetylcholine Acetylene Acetylide anion Achiral Acid Acid anhydride Acid catalyzed Acid chloride Acid dissociation constant Acid ionization constant Acid promoted Acidity Activation energy Activator Activating group AcO^- AcOH AcOR Acrylate Acrylate group Acrylic acid Acyclic Acyl chloride Acyl group Acylation Acylium ion Acyloin Adamantane Adenine Adenosine Adenosine monophosphate Adenosine triphosphate Adenylic acid Addition reaction Adrenaline Adriamycin Aglycone Agonist Ala Alanine Alcohol Alcohol dehydrogenase Alcoholysis Aldaric acid Aldehyde	Aldohexose Aldol Aldol condensation Aldol reaction Aldonic acid Aldoxime Aldopentose Aldose Aldotetrose 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-hydroxy ketone Alpha, beta-unsaturated Altrose Amalgam Ambident nucleophile Amide Amido group Amine Amine oxide Amino acid Amino acid residue Amino acid side chain Amino group Aminolysis Ammonia Ammonium cation Ammonium salt Amorphous Amoxicillin AMP Amphiphilic Amphiprotic Amphoteric Amphotericin B Ampicillin Amu Amylopectin Amylose Anabolic steroid Analgesic Analyte Anchimeric assistance Anesthetic Angle strain Anhydride Anhydrous	Aniline Anion Anion-cation interaction Anion-dipole interaction Anomer Anomeric carbon Anomeric effect Antagonist Antarafacial Anthracene Anti Anti addition Anti-inflammatory Anti-Markovnikov addition Anti-periplanar Anti-staggered Antiaromaticity Antibiotic Antibonding molecular orbital Anticancer Antidepressant Antiemetic Antifungal Antimetabolite Antioxidant Antipsychotic Antipyretic Antiviral Aprotic Aprotic solvent Aq. Aqueous Ar Arabinose Arachidic acid Arachidonic acid Arbuzov reaction Arene Arenium ion Arg Arginine Arndt-Eistert reaction Aromatic-aromatic interaction Aromatic overtones Aromatic stacking Aromaticity Arrhenius equation Arrows Aryl Aryl group Aryl halide Aryl hydrogen Ascorbate Ascorbic acid Asn Asp Asparagine Aspartic acid Aspirin Asymmetric stretching Atom economy Atomic mass unit Atomic orbital Atomic radius ATP Autoionization Autoxidation Axatorial Axial Azetidine Aziridine Azo compound Azo coupling Azo dye Return to top
B
β β-Anomer β-Branching β-Carbon β-Diketone 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 Basicity Bathochromic shift BDE Beckmann rearrangement Beer-Lambert law Beer's law Bending mode Benedict's test Benzaldehyde Benzene Benzene ring Benzo[a]pyrene	Benzoate Benzoate group Benzoic acid Benzophenone Benzoquinone Benzoyl group Benzoyl peroxide Benzyl carbocation Benzyl group Benzylic position Benzyne Bergman cyclization Beta Beta-anomer Beta branching Beta-carbon Beta-diketone 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 BH₃^.S(CH₃)₂ BH₃^.THF Bicyclic Bile acid Bimolecular Biodiesel Biopolymer Biosynthesis Birch reduction Bisphenol A	Bisulfate Blood sugar Blue shift Boat conformation Boiling point Bond angle Bond angle strain Bond change inventory Bond dipole Bond dipole moment Bond dissociation energy Bond length Bond order Bond rotation Bond stretch Bond vibration Bond-line structure Bonding molecular orbital Bonding orbital Borane Bp (BP) Branched Bredt's rule Bridged Bridgehead Broadband decoupling Bromination Bronsted acid Bronsted base Bronsted-Lowry acid Bronsted-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 Caffeine Cahn-Ingold-Prelog rules Cal Calicheamicin Calorie Calotte model Camphor Canonical form Canonical structure Carbamate Carbamate ester Carbamic acid Carbamide Carbanion Carbene Carbenoid Carbocation Carbocation fates Carbocation rearrangement Carbohydrate Carbon dioxide Carbon monoxide Carbon NMR Carbon suboxide Carbon tet Carbon tetrachloride Carbon-12 Carbon-13 Carbon-14 Carbonate Carbonic acid Carbonium ion Carbonyl Carbonyl addition reaction Carbonyl fates Carbonyl group Carbonyl oxide Carbonyl substitution reaction Carboxyl group Carboxylate Carboxylate ester Carboxylate ion Carboxylic acid Carboxylic acid derivative Carcinogen Carvone Catalyst Cat. Catalytic (catalytic amount) Catalytic hydrogenation Cation Cation-anion interaction Cation-dipole interaction Cation-pi interaction CDCl₃	Cefaclor Cellobiose Cellulose Cephalosporin CCl₄ CFC Chain initiation Chain propagation Chain reaction Chain termination Chair conformation Chair flip Chalcone Chatelier's principle ChemDraw Chemical formula Chemical ionization Chemical library Chemical shift Chemoselective Chichibabin reaction Chiral Chiral center Chlorination Chlormethine Chlorofluorocarbon Chloroform Chloroform-d Chloroformate Chlorophyll Chloroprene CHO Cholesterol Cholic acid Choline Chromatography Chromium trioxide Chromophore Chymotrypsin CI CI-MS Cis Claisen condensation Claisen reaction Claisen rearrangement Claisen-Schmidt condensation Clemmensen reduction Clinical trial Cm^-1 Coal Cocaine Codeine Coenzyme Cofactor Coil Column chromatography Combinatorial synthesis Combustion Common name Competitive inhibitor Complex carbohydrate Complex sugar Concerted reaction Condensation point	Condensation reaction Configuration Configurational isomer Conformation Conformational isomer Conformer Conjugate acid Conjugate addition Conjugate base Conjugation Constitutional isomer Constructive interference Cope elimination Cope reaction Cope rearrangement Coplanar Copolymer Corey-Fuchs reaction Coronene Corticoid COSY COT Coupling Coupling constant Covalent bond COX CPK model Cram's rule Creatine CrO₃ Crossed aldol condensation Crossed Claisen condensation Crown ether Crude oil Crystal Cubane Cumene Cumulene Cuprate Curved arrow Cyanide Cyanohydrin Cyclic Cycloaddition reaction Cycloalkane Cyclobutadiene Cyclobutane Cyclobutene Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclooctatetraene Cyclooxygenase Cyclopentadiene Cyclopentadienyl anion Cyclopentadienyl cation Cyclopentane Cyclopropane Cyclopropenyl cation Cys Cysteine Cytidine Cytosine Return to top
D
δ δ^- δ⁺ ΔE ΔΕΝ ΔG ΔG⁺⁺ ΔH ΔH_f^o ΔS 1,3-Diaxial interaction d D D-amino acid D-carbohydrate Dalton Darzens condensation Darzens reaction DBE DCM DDT Deactivating group Deactivator Decalin Decane Decantation Decarboxylation Decouple Degenerate Dehydrate Dehydration Dehydrohalogenation Deliquescent Delocalization Deoxy Deoxyadenosine Deoxyribonucleic acid Deoxyribose Deprotection Deprotonate Deprotonization DEPT Deshielded Desiccation Desolvation Destructive interference	Detergent Deuterium Deuterochloroform Dewar benzene Dextrorotatory Dextrose Diacid Diamorphine Diastereomer Diastereoselective Diastereotopic Diatomic Diaxial Diaxial interaction Diazo compound Diazo coupling Diazo dye Diazomethane Diazonium cation Diazonium salt Diazotization DIBAH DIBAL DIBAL-H Diborane Dichloromethane Dieckmann condensation Dielectric constant Diels-Alder reaction Diene Dienophile Diequatorial Diesel fuel Diethyl ether Diffraction Diffraction pattern Diffractometer Dihedral angle Dihydropyran Diisobutylaluminum hydride Dimer Dimethylallyl pyrophosphate Dimethylformamide Dimethyl sulfide Dimethyl sulfoxide Diol	Dione Dipeptide Diphosphate Dipole Dipole moment Dipole-anion interaction Dipole-cation interaction Dipole-dipole interaction Dipole-ion interaction Diradical Directing group Director Disaccharide Disiamylborane Dispersion force Disproportionation reaction Dissolving metal reduction Distillation Distribution coefficient Disubstituted Disulfide Disulfide bridge Diterpene Divalent Diversity oriented synthesis Diyne DMAPP 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 Dye Dry ice 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 Eclipsed conformation EDG ee EI EI-MS Elec Electron cloud Electron configuration 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 Electrophilic substitution Electropositive Electrostatic interaction Electrostatic potential map Elimination reaction	Empirical Emulsification Emulsify Emulsion EN Enal Enamine Enantiomeric excess Enantiomer Enantioselective Enantiotopic Endergonic Endothermic Enediyne Energy of activation Energy profile Enol Enol ether Enol form Enolate Enolization Enone Enthalpy Enthalpy of combustion Enthalpy of formation Enthalpy of hydrogenation Enzyme Ephedrine Epibatidine Epichlorohydrin Epimer Epinephrine Epoxidation Epoxide Epoxy Epoxy resin Equatorial Equial	Equilibrium Equilibrium constant Equivalent ERG Erythromycin Erythrose Ester Esterification Estrone Et Et₂O Ethane Ethanoic acid Ethanol Ethene Ether EtO^- EtOAc EtOH Ethoxide Ethyl acetate Ethyl alcohol Ethyl ether Ethyl group Ethylene Ethylene glycol Ethylene oxide Ethyne Evaporate Evaporation EWG Exact mass Excitation Excited state Exergonic Exhaustive methylation Exothermic Expanded octet Return to top
F
1^st order (kinetics) Family Fat Fatty acid FDA Fehling's test Ferrocene FID Fingerprint region Finkelstein reaction First order (kinetics) First order coupling First order splitting Fischer esterification Fischer projection Five zone analysis Flame ionization detector Fluorescence	Fluorination Folic acid Food and Drug Administration Formal charge Formaldehyde Formalin Formamide Formate Formic acid Formyl group Fourier-transform IR Fourier-transform NMR Fractional distillation Fragment ion Fragmentation Free radical Free radical halogenation	Freon Friedel-Crafts acylation Friedel-Crafts alkylation Front side attack Fructofuranose Fructose Fruit sugar FT-IR FT-NMR Fulvene Fumaric acid Fuming nitric acid Fuming sulfuric acid Functional group Furan Furanose Fused Return to top
G
Galactopyranose Galactose Gas chromatograph Gas chromatography Gas chromatography-mass spectrometry Gas phase Gasoline Gated community rule Gauche GC GC-MS Gem Geminal Geminal diol Geometric isomer Gilman reagent Gln	Glu Glucocorticoid Gluconeogenesis Glucopyranose Glucose Glutamic acid Glutamine Gly Glyceraldehyde Glycerin Glycerol Glycidic ester condensation Glycine Glycogen Glycol Glycolysis	Glycoside Glycosylceramide Goniometer Grain alcohol Grape sugar Graphene Green chemistry Grignard reaction Grignard reagent Grob fragmentation Ground state Group Guanidine Guanine Guanosine Gulose Return to top
H
1,2-H shift 1,3-H shift 1,5-H shift ¹H ¹H-NMR ²H ³H H₂O₂ H₃O⁺ hν H-bond H-NMR H-rule H⁺ ('H⁺') Halide Haloalkane Haloarene Halogenoarene Halocarbon Halogen Halogen-metal exchange Halogenation Halomethane Hammond postulate Hammond-Leffler postulate Hard Hard water Haworth projection HBr HCl HCFC Heat capacity Heat of combustion Heat of formation Heat of hydrogenation Heck reaction Hell-Volhard-Zelinsky reaction Hemiacetal Hemiketal Hemiterpene Heptane Heroin	HETCOR Heteroarene Heteroaromatic Heteroaryl Heteroatom Heterocycle Heterolysis Heterolytic bond cleavage Heterolytic cleavage Hexane Hexose HF HI High fructose corn syrup High-performance liquid chromatography High-pressure liquid chromatography High-resolution mass spectrometry Highest occupied molecular orbital Hill system His Histidine HMQC HO^- HOAc Hofmann degradation Hofmann elimination Hofmann rearrangement Hofmann's rule HOMO HOMO-LUMO gap Homochiral Homolog Homologous series Homolysis Homolytic bond cleavage Homolytic cleavage Homotopic HOOH Hooke's Law HPLC Huckel's Rule Hunsdiecker reaction Hybrid orbital	Hydrate Hydration Hydrazine Hydrazone Hydride Hydride ion Hydroboration Hydroboration-oxidation reaction Hydrocarbon Hydrobromic acid Hydrochloric acid Hydrochloride Hydrochloride salt Hydrofluoric acid Hydrofluorochlorocarbon 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 Hydrophobic vitamin Hydroquinone Hydroxide ion Hydroxyl group Hydroxyl radical Hygroscopic Hyperconjugation Hypervalent Hypochromic shift Hypsochromic shift Return to top
I
I Ibuprofen Ice Idose Ile Imidazole Imide Imine Immiscible In silico In vitro In vivo INADEQUATE Incipient carbocation IND Indole Inductive effect Infrared spectrophotometer Infrared spectroscopy Infrared spectrum Inhibitor Initiation Initiator Insoluble	Integral Integration Intercalator Intermediate Intermolecular Internal alkene Internal alkyne Intramolecular Inversion of configuration Investigational New Drug Iodination Iodoform reaction Ion Ion channel Ion-dipole interaction Ionic bond Ionic substitution reaction Ionization Ionophore IPP iPr Ipso hydrogen Ipso substitution IR	IR spectrophotometer IR spectroscopy IR spectrum Iso Isobutylene Isobutyl group Isocyanate Isoelectronic Isoleucine Isomer Isomerization Isooctane Isopentenyl pyrophosphate Isophthalic acid Isoprene Isoprenoid Isopropanol Isopropyl alcohol Isopropyl group Isotope Isoxazole Isoxazoline IUPAC Return to top
J
J (or J) J value	Jones reagent	Joule Return to top
K
K_a kcal Kekule structure K_eqKetal Ketene Keto form Ketohexose	Ketone Ketopentose Ketose Ketotetrose Ketotriose Ketoxime Kevlar KIE	Kilocalorie Kilojoule Kinase Kinetic control Kinetic isotope effect kJ Kolbe process Kolbe-Schmitt reaction Return to top
L
λ λ_max l L L-amino acid L-carbohydrate Lactam Lactate Lactate dehydrogenase Lactic acid Lactone Lactose Ladenburg benzene Laevulose LAH Lanosterol Large calorie Late transition state Lauric acid LDA Le Chatelier's principle	Lead compound Leaving group Leu Leucine Levorotatory Lewis acid Lewis acid-base adduct Lewis acid-base complex Lewis base Lewis dot structure Lewis structure LG Library LiAlH₄ Limonene LiN(iPr)₂ Lindlar catalyst Line-angle formula Linear Linoleic acid Linolenic acid	Lipid Lipophilic Lipophilic vitamin Lipophobic Lithium aluminum hydride Lithium diisopropylamide Lobe LogP London dispersion force London force Lone pair Long range coupling Lowest unoccupied molecular orbital LSD LUMO Lycopene Lys Lyseric acid diethylamide Lysine Lyxose Return to top
M
μ M M+1 M+2 m/z Macrolactone Macrolactonization Macrolide Magnetic induction Magnetic resonance imaging Major groove Major product MALDI Maleic acid Malonic acid Malonic ester synthesis Maltodextrin Maltose Mannich reaction Mannose Markovnikov addition Markovnikov's rule Marsh gas Mass spectrum Mass spectrometer Mass spectrometry Mass-to-charge ratio McLafferty rearrangement mCPBA Me Measles Mechanism Mechlorethamine Melting point Menthol MeOH Mercaptan Meso Meso compound Mesotartaric acid Mesylate Met Meta Meta director Meta-chloroperoxybenzoic acid	Metabolism Metalorganic compound Meth Methacrylate Methacrylate group Methacrylic acid Methamphetamine Methanal Methane Methanesulfonate Methanesulfonic acid Methanoic acid Methanol Methine group Methionine Methoxide Methoxy group Methyl Methyl alcohol Methyl alkyl halide Methyl carbocation Methyl carbon Methyl group Methyl hydrogen Methyl sulfide Methyl sulfoxide Methylation Methylbenzene Methylene chloride Methylene group Methyllithium Micelle Michael acceptor Michael addition Michael donor Michael reaction Michaelis-Arbuzov reaction Microscopic reversibility Mineral acid Mineralocorticoid Minor groove Minor product Miscible Mixed anhydride	Mixed Claisen condensation Mobile phase Moiety Mol Molar absorptivity Molar attenuation coefficient Molar extinction coefficient Molar mass Mole Molecular formula Molecular ion Molecular model kit Molecular orbital Molecular recognition Molecular structure Molecular weight Molecule Molozonide Monatomic Monoatomic Monohydrate Monomer Monosaccharide Monosubstituted Monoterpene Monounsaturated fat Monounsaturated fatty acid Monovalent Montreal Protocol Morphine Motif Mp MRI MS MsO MsOH MTBE Multiplet Muriatic acid Mutagen Mutarotation MW Myoglobin Myristic acid Return to top
N
N N-bromosuccinimide N-chlorosuccinimide N-oxide N-terminus N,N-dimethylformamide n n-BuLi n+1 Rule 4n+2 Rule NaBH₄ NAD⁺ NADH NaH NAS Naked proton Name reaction Naphthalene Natta projection Natural abundance Natural gas Natural product NBS NCS NDA Neat Neighbor Neighboring group participation Neo Neopentyl group Neoprene Nepetalactone	New Drug Application Newman projection Nicotine Nitranion Nitration Nitrene Nitric acid Nitric oxide Nitrile Nitro group Nitrogen inversion Nitrogen rule Nitronium cation Nitrosonium cation NMR NMR spectrometer NMR spectroscopy NMR spectrum No reaction Node NOESY Nomenclature Nominal mass Non-first order coupling Non-first order splitting Nonacidic amino acid Nonane Nonaromatic Nonbonded electron pair Nonbonded pair Nonbonding molecular orbital Noncovalent molecular force	Noncovalent molecular interaction Nondecoupled Nonequivalent Nonpolar Nonpolar covalent bond Nonpolar solvent Nonreducing sugar Nonsuperimposable Nonsuperposable Nor Norepinephrine Normal NR NSAID Nuc Nuclear magnetic resonance Nuclear spin flip Nuclear spin state Nucleic acid Nucleobase Nucleofuge Nucleophile Nucleophilic acyl substitution Nucleophilic addition Nucleophilic aromatic substitution Nucleophilic carbonyl substitution Nucleophilic substitution Nucleophilicity Nucleoside Nucleotide Nylon Return to top
O
1-Octanol O-chem ^-OAc Ochem Octane Octane number Octane rating Octet rule Oil Oleic acid Olefin Oleum Oligosaccharide OMs One equivalent One molecule rule Open octet Open valence electron count Open valence shell Opsin Optical activity Optical isomer Optical purity Optically active	Optically inactive Orbital Orbital electronegativity Orbital lobe Orbital node Organic chemistry Organic synthesis Organoborane Organocopper reagent Organohalide Organolithium reagent Organometallic compound Organophosphate Organophosphorus compound Organophosphorus reagent Orgo ORTEP Ortho Ortho/para director Orthoester Orthogonal OTf OTs Oxalic acid	Oxaphosphetane Oxazole Oxazoline Oxetane Oxidant Oxidation Oxidation number Oxidation reaction Oxidation state Oxidative cleavage Oxidizing agent Oxime Oxirane Oxo Oxonium ion Oxonium ion fates Oxyanion OxyCope rearrangement Oxymercuration-demercuration Ozone Ozone depletion Ozone hole Ozone layer Ozonolysis Return to top
P
π bond π electron π orbital π* orbital p orbital P PABA Paclitaxel PAH Palmitic acid Para Paraffin Parafilm Partial pi bond Partition coefficient PBoR PCC Penicillin Pentane Pentapeptide Pentavalent carbon Pentene Pentet Pentose Peptide Peptide bond Peptidoglycan Per Peracetic acid Peracid Pericyclic reaction Period Periplanar Peroxide Peroxide effect Peroxyacetic acid Peroxyacid PET Pet ether PETE Petrol Petroleum Petroleum ether pH Ph Ph₃PO Pharmaceutical Pharmacology Phase I trial Phase II trial Phase III trial Phase IV trial Phe Phenanthrene Phenol Phenolate Phenoxide Phenyl (phenyl group) Phenylalanine Pheromone Phosgene Phosphate Phosphate ester	Phosphate group Phosphatidic acid Phosphatidyl choline Phosphine Phosphine oxide Phosphodiester Phospholipid Phospholipid bilayer Phosphonium salt Phosphonium ylide Phosphoric acid Phosphorylation Photochemistry Photolysis Photon Phthalic acid Pi antibonding orbital Pi bond Pi-cation interaction Pi electron Pi orbital Pi stacking Pinacol rearrangement Pinacol-pinacolone rearrangement Pinner reaction Piperidine Pitzer strain pK_a pK_a1 pK_a2 pK_a3 Placebo Planar Plane polarized light Plexiglas Poisoned catalyst Polar Polar covalent bond Polar solvent Polarimeter Polarimetry Polarizability Polarization Polychloroprene Polycyclic Polycyclic aromatic hydrocarbon Polyester Polyethylene terephthalate Polymer Polymerization Poly(methyl methacrylate) Polypeptide Polysaccharide Polystyrene Polyterpene Polyunsaturated fat Polyunsaturated fatty acid Polyvinyl chloride ppm Pr Precipitate Primary Primary alcohol	Primary alkyl halide Primary amide Primary amine Primary ammonium salt Primary carbocation Primary carbon Primary hydrogen Primary structure Prismane Pro Prodrug Product Proline Prontosil Propagation Propane Propanoic acid Propargyl group Propargylic position Propene Propionic acid Propyl group Propylene Propylene glycol Propyne Prostaglandin Prostanoic acid Protease Protecting group Protection Protein Protein Data Bank Protic Protic solvent Proticity Proton Proton bus Proton NMR Proton shuttle Proton transfer Protonate p-Toluenesulfonate p-Toluenesulfonic acid PTFE pTsOH Pulmonary surfactant Purine PVC p_x orbital p_y orbital Pyran Pyranose Pyridine Pyridinium Pyridinium chlorochromate Pyrimidine Pyrophosphate Pyrrole Pyrrolidine Pyruvate Pyruvic acid p_z orbital Return to top
Q
QSAR Quantitative structure-activity relationship Quantized Quantum mechanics Quartet	Quaternary Quaternary ammonium salt Quaternary carbon Quaternary structure Quinine	Quinoline Quinone Quintet Quinuclidine Return to top
R
R R group R₂CuLi Racemate Racemic Racemic acid Racemic mixture Racemization Racemize Radical Radical anion Radical cation Radical chain reaction Radical fates Radical halogenation Radiocarbon Random coil Random screening Rate-determining step Rate-limiting step Rate equation Rate expression Rate law Rayon RCHO RCO₂H RCO₂R RCO₃H RCOOH RCOOR	rds Reactant Reaction coordinate Reaction mechanism Reaction product Reaction rate Reaction yield Reactive intermediate Reactivity-selectivity principle Rearrangement Receptor Red shift Redox reaction Reducing agent Reducing sugar Reductant Reduction Reduction reaction Reductive amination Reflection Regiochemistry Regioselective Relative abundance Relative configuration Relative intensity Relaxation Relaxation time Residue Resolution Resonance	Resonance contributor Resonance contributor preference rules Resonance energy Resonance hybrid Resonance structure Retention of configuration Retinal Retinaldehyde Retinol Retinol binding protein Retro-aldol reaction Retro-Claisen condensation Retrosynthetic analysis Retrosynthesis Rhodopsin Ribofuranose Ribonucleic acid Ribose Ring flip Ring strain Ritter reaction RLi RNA RO^- ROAc Robinson annelation Robinson annulation ROH Rosenmund reduction Rubbing alcohol Return to top
S
1,2-shift 1,3-shift 2^nd order (kinetics) 3,3-shift σ bond σ electron σ orbital σ* orbital S s orbital S-adenosylmethionine s-cis s-BuLi s-trans Saccharide Salicylic acid Salt SAM Sandmeyer reaction Sanger's reagent Saponification SAR Saturated Saturated fat Saturated fatty acid Sawhorse projection Saytsev's rule Saytzeff's rule Schiemann reaction Schiff base Sec Sec-butyl group Seco acid Second order (kinetics) Second order coupling Second order splitting Secondary Secondary alcohol Secondary alkyl halide Secondary amide Secondary amine Secondary ammonium salt Secondary carbocation Secondary carbon Secondary hydrogen Secondary structure Selenocysteine Self condensation Semicarbazone Septet Ser Serine Serine protease Sesquarterpene Sesquiterpene Sesterterpene Sextet Shielded Side chain Sigma bond Sigma electron Sigma orbital Sigma* orbital Sigmatropic reaction Signal Signal molecule	Significant resonance contributor Silyl enol ether Silyl ether Simmons-Smith reaction Simple carbohydrate Simple distillation Simple sugar Single bond Singlet Singly occupied molecular orbital Skeletal formula Skeletal isomer Skeletal structure Small calorie S_N1 mechanism S_N2 mechanism S_NAr mechanism Soap Sodamide Sodium amide Sodium borohydride Sodium hydride Soft Solubility Solute Solvation Solvent Solvent shell Solvolysis SOMO sp orbital sp² orbital sp³ orbital Space filling model Specific rotation Spectrometer Spectrometry Spectrophotometer Spectroscopy Spectrum Sphingolipid Sphingosine Spin quantum number Spin-spin coupling Spiro Splitting Spontaneous resolution Squalene Squalene oxide Squiggly line Staggered Staggered conformation Standard amino acid Starch Starting material Stationery phase Steam Stearic acid Stepwise reaction Stereocenter Stereochemistry Stereoelectronic effect Stereoisomer Stereoselective Stereospecific	Steric effect Steric hindrance Steric number Steric strain Steroid Sterol Stille coupling Stille reaction Stobbe condensation Stoichiometry Stork acylation reaction Stork enamine reaction Strain Stretching frequency Structure-activity relationship Structural isomer Styrene Styrofoam Sublimation Substituent Substituted Substitution nucleophilic 1^st order Substitution nucleophilic 2^nd order Substitution nucleophilic bimolecular Substitution nucleophilic unimolecular Substitution reaction Substrate Substrate mimic Succinic acid Sucralose Sucrose Sugar Suicide inhibitor Sulfa drug Sulfanilamide Sulfate Sulfhydryl group Sulfide Sulfonamide Sulfonate Sulfonate anion Sulfonate ester Sulfonate ion Sulfonation Sulfone Sulfonic acid Sulfonium ion Sulfonium salt Sulfonyl chloride Sulfoxide Sulfur dioxide Sulfur trioxide Sulfuric acid Superacid Supercoil Supercoiling Superimposable Superoxide Superposable Suprafacial Surfactant Symmetric stretching Syn Syn addition Syn-periplanar Return to top
T
[TS]⁺⁺t-BuLiTalose Tartaric acid Tautomer Tautomerization Taxol TBAF tBDMS group tBDPS group tBu tBuO^- tBuOH TCD Teflon Teratogen Terephthalic acid 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 ammonium salt Tertiary carbocation Tertiary carbon Tertiary hydrogen Tertiary structure Tetra-n-butylammonium fluoride Tetrachloromethane Tetracyclic Tetracycline Tetrahedral adduct Tetrahedral carbon	Tetrahedral intermediate Tetrahydrofuran Tetrahydropyran Tetramer Tetramethylsilane Tetrapeptide Tetrasubstituted Tetraterpene Tetravalent Tetrose Texas carbon TfO TfOH Thalidomide Thermal conductivity detector Thermodynamic control Thermodynamically spontaneous THF Thiazole Thioacetal Thioester Thioether Thiol Thiolate Thiolester Thionyl chloride Thiophene Thiophenol THP Thr Threonine Threose Thymidine Thymine TMS TMS group Tollen's reagent Tollens' test Toluene Toluenesulfonate Toluenesulfonic acid Torsional strain Tosylate Total synthesis Trans	Trans fat Transamidation Transamination Transesterification Transition state Transition state analog Transmetalation Transmute Transpeptidase Trehalose Triacylglyceride Triacylglycerol Tricyclic Triflate Triflic acid Trifluoroethanol Trifluoroethoxide ion Trifluoromethanesulfonate Trifluoromethanesulfonic acid Trifluoromethyl group Triglyceride Trimolecular Trimer Triol Triose Trioxolane Tripeptide Triphosphate Triple bond Triplet Triplet of doublets Trisubstituted Triterpene Tritium Trivalent Tropylium cation Trp Tryptophan TS TsO TsOH Two-dimensional NMR Tyr Tyrosine Return to top
U
Ultraviolet spectroscopy Ultraviolet-visible spectroscopy Unbranched Undecane Unimolecular Unsaturated	UN Unionized Upfield Uracil Urea	Urethane Uridine Uronic acid UV UV-vis Return to top
V
Vacuum distillation Val Valence Valence electron Valence shell Valine Van der Waals force Van der Waals repulsion van der Waals strain Vapor pressure	Vaporization Vaporize Vic Vicinal Vicinal diol Vinegar Vinyl chloride Vinyl group Vinylic carbocation	Vinylic hydrogen Vinylic position Vitalism Vitamin Vitamin A Vitamin C Vitamin E Volatile VSEPR theory Return to top
W
Wagner-Meerwein shift Walden inversion Water Water vapor Watson-Crick base pair Wavelength	Wavenumber Wavy line Wax Wedge Wieland-Miescher ketone Williamson ether synthesis	Wittig reaction Wolff-Kishner reduction Wood alcohol Woodward-Hoffmann rules Wurtz coupling Wurtz reaction Return to top
X
X-ray crystallography X-ray diffraction X-ray diffractometer	Xanthine Xylose	Xylene Xylulose Return to top
Y
Yield	Ylide	Return to top
Z
Z Zaitsev's Rule	Zigzag structure	Zwitterion Return to top

Copyright 2010-2017 Steven A. Hardinger, Department of Chemistry & Biochemistry, UCLA. All rights reserved. For images with permission, click the image to review the permission. All other images property of the author or are in the public domain.