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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Symbols

Symbols
(-) (+) 1^o	2^o 2D-NMR 3^o	α β
A
α,β-Unsaturated α-Amino acid α-Carbon α-Helix α-Hydrogen α-Tocopherol Absolute configuration Abstraction Acetal Acetic acid Acetone Acetonitrile Acetyl CoA Acetyl group Acetylene Acetylide anion Achiral Acid anhydride Acid chloride Acid ionization constant Activation energy Activator Activating group Acyclic Acyl chloride Acyl group Acylation Acylium ion Adenine Addition reaction Agonist Alanine Alcohol Alcoholysis Aldehyde Aldohexose Aldol Aldol condensation Aldol reaction Aldopentose	Aldose Aldotriose Aliphatic Alkane Alkene Alkoxide Alkyl group Alkyl halide Alkylammonium salt Alkylate Alkylation Alkyne Alkyne anion Alkynyl anion Allyl carbocation Allyl group Allylic position Alpha Alpha-amino acid Alpha-carbon Alpha-helix Alpha-hydrogen Alpha,beta-unsaturated Altrose Ambident nucleophile Amide Amine Amino acid Amino acid residue Aminolysis Ammonia Ammonium salt Amoxicillin Ampicillin Amylopectin Amylose Angle strain Anhydride Anhydrous Aniline	Anion Anion-cation interaction Anomer Anomeric carbon Anomeric effect Antagonist Anti Anti addition Anti-Markovnikov addition Anti-periplanar Antiaromaticity Antibiotic Antibonding molecular orbital Antimetabolite Antioxidant Aprotic solvent Aqueous Ar Arabinose Arene Arenium ion Arginine Aromatic stacking Aromaticity Arrhenius equation Arrows Aryl Ascorbate Ascorbic acid Asparagine Aspartic acid Aspirin Asymmetric stretching Atomic orbital Autoionization Autoxidation Axatorial Axial Azo compound Azo coupling
B
β-Carbon β-Elimination β-Hydrogen β-Hydroxy aldehyde β-Hydroxy ester β-Hydroxy ketone β-Lactam β-Pleated sheet β-Sheet 1,3-Butadiene Backside attack Baeyer-Villiger oxidation Barrier to rotation Base peak BDE Bending mode Benzene Benzene ring Benzyl group	Benzylic position Benzoic acid Benzoyl group Beta Beta-carbon Beta-elimination Beta-hydrogen Beta-hydroxy aldehyde Beta-hydroxy ester Beta-hydroxy ketone Betaine Beta-sheet Beta-lactam Bicyclic Biodiesel Biopolymer B_⁰ Boat conformation Boiling point	Bond angle Bond dipole Bond dissociation energy Bond rotation Bond stretch 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 Butadiene Butane
C
1,3-Cyclobutadiene 1,3,5,7-Cyclooctatetraene ¹³C-NMR Cahn-Ingold-Prelog rules Calicheamicin _γ1^I Carbanion Carbocation Carbocation fates Carbohydrate Carbon NMR Carbonyl Carbonyl fates Carbonyl group Carboxyl group Carboxylate Carboxylic acid Carcinogen Canonical form Canonical structure Catalyst Cat. Catalytic Catalytic hydrogenation Cation Cation-anion interaction Cation-pi interaction Cefaclor	Cellulose Cephalosporin CFC Chain reaction Chair conformation Chair flip ChemDraw Chemical shift Chichibabin reaction Chiral Chiral center Chlorination Chlorofluorocarbon Chloroform Chymotrypsin Cis Claisen condensation Claisen reaction Clemmensen reduction Coenzyme Coil Combinatorial synthesis Competitive inhibitor Concerted reaction Configuration Configurational isomer Conformation Conformational isomer	Conformer Conjugate acid Conjugate base Conjugation Constitutional isomer COSY COT Coupling Coupling constant Covalent bond Creatine Crystal Curved arrow Cyclic Cycloaddition reaction Cycloalkane Cyclobutadiene Cyclobutane Cyclooctatetraene Cyclopentadiene Cyclopentadienyl anion Cyclopentadienyl cation Cyclopropane Cyclopropenyl cation Cyclohexane Cyclopentane Cysteine Cytosine
D
δ δ^- δ⁺ ΔΕΝ ΔH_f d D DBE DCM Deactivating group Deactivator Decane Decouple Degenerate Delocalization Deoxyribonucleic acid Deoxyribose Deprotection Deprotonate Deprotonization DEPT Deshielded Desolvation	Detergent Dextrorotatory Diastereomer Diazo compound Diazo coupling Diazonium cation Diazotization Dichloromethane Dieckmann condensation Dielectric constant Diels-Alder reaction Diene Dienophile Diethyl ether Dihedral angle Dimethylformamide Dimethylsulfoxide Diol Dipeptide Diphosphate Dipole Dipole moment Dipole-dipole interaction	Directing group Director Disaccharide Dispersion force Disubstituted Disulfide Disulfide bridge Divalent Diversity oriented synthesis DMF DMSO DNA DNA alkylator DNA cutter Dodecane Double blind trial Double bond Double bond equivalent Doublet Doublet of doublets Doublet of triplets Downfield Drug
E
ε E E1 mechanism E1_cb mechanism E2 mechanism E_a E_act Early transition state EAS Eclipsed EDG ee Elec Electron delocalization Electron density Electron donating group Electron group Electron withdrawing group Electronegativity Electrophile Electrophilic aromatic substitution	Electrophilic addition reaction Electrostatic potential map Elimination reaction Empirical EN Enamine Enantiomeric excess Enantiomer Endergonic Endothermic Energy of activation Energy profile Enol Enol form Enolate Enolization Enone Enthalpy of formation Enzyme Epibatidine Epoxide Equatorial	Equial Equilibrium constant Equivalent Erythrose Ester Et Ethane Ethanol Ethene Ether Ethoxide ion Ethyl acetate Ethyl alcohol Ethyl ether Ethyl group Ethylene Ethyne EtOH EWG Exergonic Exothermic
F
Fatty acid FDA Fingerprint region Finkelstein reaction First order coupling First order splitting Fischer esterification	Fischer projection Folic acid Formal charge Fragmentation Free radical Freon Friedel-Crafts acylation	Friedel-Crafts alkylation Fructose Functional group Furan Furanose Fused
G
Galactose Gauche Geminal Geometric isomer Glucopyranose Glucose Glutamic acid	Glutamine Glyceraldehyde Glycerin Glycerol Glycine Glycolysis Glycoside	Grain alcohol Grignard reaction Grignard reagent Group Guanine Gulose
H
[1,3-H] shift 1,3 hydrogen shift ¹H-NMR hν H-bond H-NMR H⁺ ("H⁺") Haloalkane Hammond Postulate Hard Hard water Haworth projection Heat of formation Hemiacetal Hemiketal Heptane HETCOR Heteroarene Heteroaromatic	Heteroaryl Heteroatom Heterocycle Heterolytic cleavage Hexane Hexose Highest Occupied Molecular Orbital Histidine HMQC HOAc Hofmann degradation Hofmann elimination HOMO HOMO-LUMO gap Homolog Homolytic cleavage Hooke's Law Hückel’s Rule	Hybrid orbital Hydride Hydrocarbon Hydrochloric acid Hydrogen bond Hydrogen bond acceptor Hydrogen bond donor Hydrogen chloride Hydrogen rule Hydrolysis Hydronium ion Hydrophilic Hydrophobic Hydrophobic effect Hydroxide ion Hydroxyl group Hydroxyl radical Hyperconjugation
I
I Idose Imidazole Imine In silico In vitro In vivo INADEQUATE Incipient carbocation IND Indole Inductive effect Infrared spectroscopy Infrared spectrum Inhibitor Initiation	Integral Integration Intercalation Intercalator Intermediate Intermolecular Internal alkene Internal alkyne Intramolecular Inversion of configuration Iodoform reaction Ion channel Ion pair mechanism Ion-dipole interaction Ionic bond Ionic substitution reaction	Ionization Ionophore iPr IR spectroscopy IR spectrum Iso Isoleucine Isomer Isobutyl group Isoelectronic Isopropanol Isopropyl alcohol Isopropyl group Isotope IUPAC
J
J
K
K_a kcal kJ Kekulé structure	K_^eq Ketal Keto form Ketone	Ketohexose Ketopentose Ketose Kinetic control
L
l L Lactam Lactone Lactose Late transition state LDA Le Chatelier's Principle Lead compound Leaving group	Leucine Levorotatory Lewis acid Lewis base Lewis dot structure Lewis structure LG Library Linear Lipid	Lipophilic Lipophobic Lithium diisopropylamide London dispersion force London force Lone pair Long range coupling Lowest Unoccupied Molecular Orbital LUMO Lysine
M
μ M M+1 M+2 m/z Magnetic anisotropy Magnetic induction Magnetic resonance imaging Maltose Major product Mannose Markovnikov addition Markovnikov's Rule Mass-to-charge ratio Me Mechanism Mechlorethanamine MeOH Mercaptan Meso	Meso compound Mesylate Meta Meta director Metabolism Methane Methanesulfonate Methanol Methine group Methionine Methoxide Methoxy group Methyl Methyl alcohol Methyl carbocation Methyl carbon Methyl group Methyl hydrogen Methylene chloride	Methylene group Micelle Mineral acid Minor product Molecular ion Molecular model kit Molozonide Molecular orbital Monoatomic Monosaccharide Monosubstituted Monounsaturated Monovalent Montreal Protocol Motif MRI Multiplet Mutagen Mutarotation
N
N n n+1 Rule 4n+2 Rule N,N-dimethylformamide NAS Naked proton Name reaction Naphthalene Natural abundance Natural product NDA Neighbor Neo Nepetalactone Newman projection Nitranion	Nitration Nitrile Nitro Nitrogen inversion Nitrogen rule Nitronium cation Nitrosonium cation NMR NMR spectrometer No reaction Nomenclature Non-first order coupling Non-first order splitting Nonane Nonbonded electron pair Nonbonded pair	Noncovalent molecular force Nondecoupled Nonequivalent Nonpolar Nonpolar solvent Nonsuperimposable Nonsuperposable NR Nuc Nucleophile Nucleoside Nucleotide Nuclear magnetic resonance Nucleophilic acyl substitution Nucleophilic aromatic substitution Nucleophilic carbonyl substitution
O
1-Octanol OCATSA Octane Octane rating Octet rule Oil One equivalent One molecule rule Open octet Optical activity Optically active Optically inactive	Orbital Orbital electronegativity Organic synthesis Organoborane Organometallic Ortho Ortho/papa director Orthoester OTf OTs Oxaphosphetaine Oxazole	Oxidation Oxidation reaction Oxidizing agent Oxonium ion Oxonium ion fates Oxyanion Ozone Ozone depletion Ozone hole Ozonide Ozonolysis
P
π bond π orbital π* orbital p orbital PABA Para Partial pi bond Penicillin Pentane Pentapeptide Pentavalent carbon Pentet Pentose Peptide bond Peptidoglycan Periplanar Peroxide Peroxide effect Ph Pharmacology Phase I trial Phase II trial Phase III trial Phase IV trial Phenol Phenyl (phenyl group) Phenylalanine Phospholipid Phospholipid bilayer Phosphate Phosphodiester Phosphoric acid Photochemistry Photolysis	Pi bond 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 Polymer Polysaccharide Polyunsaturated ppm Pr Primary Primary alcohol Primary alkyl halide Primary amide Primary amine Primary carbocation Primary carbon Primary hydrogen Primary structure Prodrug	Product Proline Propagation Propane Propargyl group Propargylic position Propene Propyl group Propylene Propyne Prostaglandin Protease Protection Protecting group Protein Protic Protic solvent Proticity Proton bus Proton NMR Proton shuttle Protonate p-Toluenesulfonate p-Toluenesulfonic acid pTsOH Pulmonary surfactant Purine Pyran Pyranose Pyridine Pyrimidine Pyrophosphate Pyrrole Pyrrolidine
Q
QSAR Quartet	Quaternary ammonium salt Quaternary (4^o) carbon	Quaternary structure
R
R R group Racemate Racemic Racemic mixture Radical Radical chain Radical fates Random coil Random screening Rate-determining step Rate-limiting step RCOOH RCOOR rds Reactant	Reaction coordinate Reaction mechanism Reaction rate Reactive intermediate Reactivity-selectivity principle Receptor Reducing agent Reduction Reduction reaction Regiochemistry Regioselective Regiospecific Relaxation Residue Resolution Resonance	Resonance contributor Resonance energy Resonance hybrid Resonance structure Retention of configuration Retroaldol reaction Retrosynthesis Ribofuranose Ribonucleic acid Ribose Ring flip Ring strain RNA RO^- ROH Rubbing alcohol
S
σ bond σ orbital σ* bond σ* orbital S s orbital S-adenosylmethionine s-cis s-trans Saccharide Salicyclic acid SAM SAR Saturated 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 Serine Serine protease Sextet Shielded Sigma bond Signal Single bond Singlet	Skeletal formula Skeletal isomer Skeletal structure S_N1 mechanism S_N2 mechanism Soap Soft Solvation Solvent Solvent shell Solvolysis sp orbital sp² orbital sp³ orbital Space filling model Specific rotation Spectrometry Spectroscopy Spin-spin coupling Spiro Splitting Spontaneous resolution Staggered Standard amino acid Starch Starting material Stereocenter Stereochemistry Stereoisomer Stereoselective Stereospecific Steric effect Steric hindrance	Steric number Steric strain Steroid Strain Stretching frequency Structure-activity relationship Structural isomer Substituent Substituted Substitution reaction Substrate Substrate mimic Sucrose Suicide inhibitor Sulfa drug Sulfanilide Sulfhydryl group Sulfide Sulfonamide Sulfonate Sulfonation Sulfone Sulfonic acid Sulfonyl chloride Sulfoxide Sulfuric acid Supercoiling Superimposable Superoxide Superposable Symmetric stretching Syn Syn addition Syn-periplanar
T
[TS]^‡Talose Tautomerization Tautomer tBu tBuOH Teratogen Terminal alkene Terminal alkyne Termination Tert Tert-butanol Tert-butoxide Tert-butyl group Tertiary Tertiary alcohol Tertiary alkyl halide Tertiary amide Tertiary amine Tertiary carbocation Tertiary carbon Tertiary hydrogen Tertiary structure Tetrahedral adduct Tetrahedral intermediate Tetrahydrofuran	Tetramethylsilane Tetrapeptide Tetrasubstituted Tetrose Tetravalent TfO Thalidomide Thermodynamic control THF Thiazole Thioester Thioether Thiol Thiolate Thiolester Thiophene Threonine Threose Thymine TMS Toluene Toluenesulfonate Toluenesulfonic acid Torsional strain Tosylate Trans	Transamidation Transamination Transesterification Transition state Transition state analog Transmute Triacylglyceride Tricyclic Triflate Trifluoromethanesulfonate Triglyceride Triose Tripeptide Triphosphate Triple bond Triplet Triplet of doublets Trisubstituted Trivalent Tryptophan TS TsO TsOH Two-dimensional NMR Tyrosine
U
Unbranched Undecane	Unsaturated UN	Upfield Uracil
V
Valence Valine Van der Waals force Van der Waals repulsion	Vicinal Vinyl group Vinylic Vitalism	Vitamin Vitamin C Vitamin E VSEPR
W
Walden inversion Water Wavenumber Wavy line	Wax Wedge Williamson ether synthesis	Wittig reaction Wolff-Kischner reduction Wood alcohol
X
X-ray crystallography	X-ray diffraction
Y
Ylide
Z
Z	Zaistev's Rule	Zwitterion