Organic Chemistry Glossary

Glossary of Terms in Undergraduate Organic Chemistry & Their First Appearance Headings

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Abbreviation, Term, Symbol, Unit Class       Database Headings
Δ; ↑↓ LAB heat; reflux
(+)   (dextrorotatory) I Stereochemistry
(-)    (levorotatory) I Stereochemistry
1,2-addition (direct addition) I Electrophilic Addition
[1,2]-hydride shift I Carbocations
[1,2]-alkyl shift I Carbocations
1º, 2º, 3º, 4º I Classifying Carbons, C-Substituents
[1,3] migration II Pericyclic reactions
1,4-addition (conjugate addition); Michael rxn II Michael addition
[1,5] migration II Sigmatropic Rearrangements
[1,7] migration II Sigmatropic Rearrangements
[2+2] cycloaddition II Pericyclic Reactions
[3+2] cycloaddition II Pericyclic Reactions
[4+2] cycloaddition I Pericyclic Reactions
9-BBN I Electrophilic Addition
absolute (pure, neat) LAB
absolute configuration I Stereochemistry
absorbance spectrum I IR, UV-Vis Spectroscopy
acetal II Aldehydes and Ketones
Acetoacetic Ester synthesis II Named Reactions
acetylene I Alkynes
acetylide Anion I Alkynes
achiral I Stereochemistry
acid anhydride II Carboxylic Acid Derivatives
acid-catalyzed I Electrophilic Addition
acid halide (also Acyl halide) II Carboxylic Acid Derivatives
acid ionization constant (Ka) I Acids and Bases
activated charcoal (Norit); decolorizer LAB
activation energy GEN Kinetics vs. Thermodynamics
activating group (EDG) II Reactions of Benzene
actual yield (% yield) LAB
acyl group    (also acetyl when = ‘Ac’) II Carboxylic Acid Derivatives
acylation reactions II Reactions of Benzene
acylium ion II Reactions of Benzene
Adenine (A) II Nucleic Acids
Adenosine II Nucleic Acids
addition reactions I Electrophilic Addition
adsorption LAB
Alanine (Ala or A) II Peptides and Proteins
alcohol (ROH) I Alcohols, Ethers, Epoxides
alcoholysis II Carboxylic Acid Derivatives
aldehyde II Ketones and Aldehydes
aldohexose II Sugars
Aldol reaction II Ketones and Aldehydes II
Aldol condensation II Ketones and Aldehydes II
aldose sugar II Sugars
alkali metal GEN
alkaline GEN  Acids & Bases
Alkaline Earth Metals GEN  The Periodic Table
alkaloid II Amines; Natural Products
alkane I Alkanes
alkene I Alkenes
alkyne I Alkynes
alkoxide (-OR) I Substitution
alkyl group/substituent I Nomenclature
alkyl halide (R-X) I Nomenclature
allene (1,2- or cumulated diene) I Dienes; Stereochemistry
allyl group/position I Resonance
allylic carbocations I Resonance
allylic position I Resonance
amino acid II Peptides and Proteins
α-anomer or epimer (internal acetal-axial bond) II Sugars
α-carbon (a carbon attached to functionality) II Functional groups
alpha-helix II Peptides and Proteins
anisotropy I NMR Spectroscopy
amalgam II Redox Reactions
ambident II Carbonyl Compounds
amide II Carboxylic Acid Derivatives
amine I Amines I & II
amine oxide (N-oxide) I Elimination
amu (Dalton) GEN
angle strain I Conformational Analysis
anhydrides, of acids II Carboxylic Acid Derivatives
anhydrous LAB
anion GEN
annealing II Nucleic Acids
anomer / anomeric II Sugars; Stereochemistry
anomeric carbon II Sugars
anomeric effect (negative hyperconjugation) II Electron Delocalization
anti conformation I Stereochemistry
anti addition I Electrophilic Addition
anti-Markovnikov Addition/regiochemistry I Regiochemistry
antiperiplanar I Conformational Isomerism
anti-aromaticity II Aromaticity
antibiotic II Drugs and Enzymes
anti-bonding molecular orbital I Molecular Orbital Theory
aprotic (solvent) I Solvents
aqueous I Solvents
arenium ion/intermediate I Aromatic Substitution
Arginine (Arg or R) II Amino Acids and Proteins
Arrhenius equation/constant/acid-base I Kinetics vs. Thermodynamics
aryl or Ar- (aromatic substituent) I Nomenclature
aryl halide (Ar-X) II Functional Groups
Asparigine (Asn or Q) II Amino Acids and Proteins
Aspartic Acid/Aspartate (Asp or E) II Amino Acids and Proteins
asymmetric (chiral) I Stereochemistry
asymmetric stretch/bend/wag I IR Spectroscopy
atomic mass GEN  The Periodic Table
atomic number GEN  The Periodic Table
atomic orbital (s, p, d, f) GEN  Covalent Bonding
atomic radius GEN  The Periodic Table
ATP (adenosine triphosphate) II Nucleic Acids
Avagadro’s Number (6.022 x 10-23) GEN  Stoichiometry
axial I Conformational Analysis
azeotrope; azeotropic mixture LAB
azide anion I Substitution
aziridine I Amines; Heterocycles
Azimuthal Quantum Number I Electron Configuration
diazo coupling II Reactions of Benzene
backside attack I Nucleophilic Substitution
Baeyer-Villiger Oxidation II Aldehydes and Ketones
banana bonds (Walsh cyclopropane) I Cycloalkanes
base (Brønsted or Lewis) I Acids and Bases
base-catalyzed I Catalysis
base pairing II Nucleic Acids
Bond Dissociation Energy (BDE) I Covalent Bonds; Radicals
bending mode (IR) I IR Spectroscopy
benzylic carbocation I Carbocations
benzyl group (PhCH2-) I Nomenclature
benzylic position I Resonance
Benzyne II Reactions of Benzene
ß-anomer II Sugars
ß-carbon I Elimination, Conjugate addition
ß-elimination I Elimination
betaine II Aldehydes and Ketones
ß-pleated sheet II Peptides and Proteins
bicyclic (bridged or spiro-) II Nomenclature
bimolecular (2nd order) I Elimination, Substitution
biosynthesis II Synthetic Strategy
boat conformation I Conformational Analysis
boiling point (BP) I Alkanes
bond angle I Bonding & Hybridization
bond dipole I Bonding and Hybridization
bond length I Representing Organic Compounds
bond order GEN
bond rotation I Conformational Analysis
bond stretch I IR Spectroscopy
bond-line structure I Representing Organic Structures
Bonding Molecular Orbital (σ or π) I Molecular Orbital theory
borane I Electrophilic Addition
branching I Alkanes; Nomenclature
bridged I Polycyclic Compounds
bromination I Electrophilic Addition & Substitution
Brønsted Acid-Base Theory/Definition I Acids and Bases
butyl- I Nomenclature
Cahn-Ingold-Prelog (C-I-P) Rules I Nomenclature; Stereochemistry
carbanion II Carbanions; Reactive intermediates
carbocation or carbenium I Carbocations
carbohydrate (CH2O)n II Sugars
Carbon-13 NMR I NMR Spectroscopy
carbonyl (C=O) II Ketones and Aldehydes
carboxylate (-CO<2) II Carboxylic Acid Derivatives
carboxylic acid (-CO2H) II Carboxylic Acid Derivatives
carboxylic acid derivative II Carboxylic Acid Derivatives
canonical form (or mesomer) I Resonance
catalyst I Kinetics & Thermodynamics
catalytic hydrogenation I Redox Reactions; Addition
chain initiation (of radical reactions) I Radicals
chain propagation  (of radical reactions) I Radicals
chain termination  (of radical reactions) I Radicals
chair conformations I Conformational Analysis
chair flip (cyclohexane) I Conformational Analysis
chemical shift (δ) [ppm] I NMR Spectroscopy
chiral I Stereochemistry
chirality (or asymmetric) center I Stereochemistry
chlorination I,II Electrophilic Addition
cholesterol II Fats & Lipids
chromatography (several kinds) LAB Chemical Separation
cis I Stereochemistry
Claisen condensation II Reactions at the α-carbon
Claisen rearrangement II Pericyclic Reactions
Clemmensen reduction II Redox Reactions
combustion I Alkanes
concerted (synchronous) reaction I Substitution
condensation reaction II Condensation Reactions
condensed formula (space-saving) I Representing Organic Compounds
configuration (absolute and relative) I Stereochemistry
configurational (stereo-) isomers I Stereochemistry
conformation I Isomerism
conformational isomers (conformers) I Isomerism
conformers I Isomerism
conjugate acid I Acids and Bases
conjugate base I Acids and Bases
conjugation I Resonance
constitutional (“structural”) isomers I Isomerism
coordination compounds I Organotransition Metal Chemistry
coupling I NMR Spectroscopy
coupling constant (J) [Hz] I NMR Spectroscopy
covalent bond I Atoms and Molecules
crown ethers (#C-cr-#O) I Alcohols, Ethers, Epoxides
cuprates I,II Organometallic Compounds
curved arrow formalism I Arrow pushing and Mechanism
cycloaddition reaction I Pericyclic Reactions
cycloalkane I Alkanes, Nomenclature
cyclobutadiene II Aromaticity
cyclooctatetraene II Aromaticity
cyclopentadienyl anion II Aromaticity
cyclopentadienyl cation II Aromaticity
cyclopropane I Cycloalkanes
cyclopropenyl cation II Aromaticity
Cysteine (Cys or C) II Peptides and Proteins
cystine bridge (Cys-Cys) II Peptides and Proteins
Cytosine (C) II Nucleic Acids
d- (same as (+)) I Stereochemistry
D- (dextrorotatory) I Stereochemistry
Dalton [Da] or [amu] GEN (an atomic mass unit)
deactivating group II Reactions of Benzene
deactivator II Reactions of Benzene
decarboxylation II Condensation Reactions
decomposition LAB
degenerate I Resonance Structures
delocalization I Resonance Structures
Deoxyribonucleic Acid II Nucleic Acids
deprotection / deblocking II Ketones and Aldehydes
deprotonate/deprotonation I Acids & Bases
DEPT II NMR spectroscopy
deshielded (downfield) I NMR spectroscopy
desolvation or dissolution I Solvents and Solutions
destructive interference I MO theory; NMR spectroscopy
detergent II Fats and Lipids
detonation LAB
deuterium (“heavy” hydrogen) 2H I Mass Spectrometry
Dewar benzene I Benzene & Aromatics
dextrorotatory (D or d or +) I Stereochemistry
dextrose (D-glucose) I Sugars
diastereomer I Stereochemistry
diatomic (A2) GEN
diaxial interaction I Conformational Analysis
diazonium ion II Reactions of Benzene
diazonium salt II Reactions of Benzene
diazotization II Reactions of Benzene
DIBAL or DIBAL-H II Redox Reactions
dichloromethane  (methylene chloride) LAB Solvents (Chart)
dichromate I Redox Reactions
Dieckmann Condensation II Condensation Reactions
dielectric constant I Solvents
Diels-Alder Reaction; [4+2] cycloaddition I Dienes, Pericyclic Reactions
diene I Dienes, Conjugation
dieneophile I Dienes, Pericyclic Reactions
diethyl ether (Et2O I Ethers; Solvents
diffraction I Refractive Index
diffraction pattern I Refractive Index
dihedral angle I Conformational Analysis
dimer I Intermolecular forces
dimethylformamide (DMF) I Solvents
dimethyl sulfide (DMS) I Solvents
dimethyl sulfoxide (DMSO) I Solvents
diol I Redox Reactions
dipeptide I Peptides and Proteins
dipoles I Bonding and Hybridization
dipole moment GEN Covalent Bonds
disproportionation II Redox Reactions
diprotic acid GEN
diradical, triplet state II Alkenes, aromatization
directing group I Reactions of Benzene
disaccharide II Sugars
Dispersion Force (London Force) I Intermolecular Forces
distillation LAB
di-substituted I Nomenclature
disulfide    -SS- I Peptides and Proteins
disulfide bridge  -cys-S-S-cys- I Peptides and Proteins
divalent anions and cations I Formal Charge
double or (π) bond I Alkenes
Double Bond Equivalent (DBE) IU or IHD I Index of Unsaturation/IU/IHD
double-headed arrow (→) I Arrow Pushing and Mechanism
double helix II Nucleic Acids
doublet (d) I NMR Spectroscopy
downfield (de-shielded) I NMR Spectroscopy
drug II Drugs, Enzymes, and Activation
ε (electrical permittivity) I Solvents
E (Ger. entgegen) I Stereochemistry
E1 Mechanism I Elimination
E1 Reaction I Elimination
E1CB Mechanism I Elimination
E2 Mechanism I Elimination
E2 Reaction I Elimination
Ea I Kinetics & Thermodynamics
early (reactant-like) transition state I Kinetics & Thermodynamics
eclipsed I Conformational Analysis
% ee (enantiomeric excess) I Stereochemistry
election configuration I Electron Configuration
electron delocalization I Resonance; Conjugation
Electron Donating Group (EDG) I Dienes
electron pair repulsion I Structure and Bonding
electron-sea (‘sea-of-electrons’) I Special Topic
Electron Withdrawing Group (EWG) I Dienes
electronegative GEN  Covalent Bonds
electronegativity GEN  Covalent Bonds
electroneutral (non-polar) GEN  Covalent Bonds
electrophile I Reactions
Electrophilic Addition Reaction I Alkenes
Electrophilic Aromatic Substitution II Reactions of Benzene
electropositive GEN  Covalent Bonds
elimination reaction (e.g. I Eliminations
emulsion II, LAB Fats and Lipids
enamines II Ketones and Aldehydes; Amines
enantiomeric excess (% ee) I Stereochemistry
enantiomers I Stereochemistry, Chirality
endergonic (+ΔG) I Kinetics and Thermodynamics
endothermic (+ΔH) I Kinetics and Thermodynamics
energy profile or Reaction Coordinate Diagram I Kinetics and Thermodynamics
enols I Tautomerization
enolates II Reactivity at the α-Carbon
enolization II Reactivity at the α-Carbon
enone II Enones and Enoates
enthalpy (heat) of combustion I Kinetics and Thermodynamics
enthalpy of formation I Kinetics and Thermodynamics
enthalpy of hydrogenation I Kinetics and Thermodynamics
enzyme II Kinetics and Thermodynamics
epoxides I Alcohols, ethers, epoxides
equations of state GEN
equilibrium GEN
equilibrium constant (Keq) GEN
equatorial I Conformational analysis
equivalent (equimolar or stiochiometric) I Lab
ester II Carboxylic Acid Derivatives
Et- (ethyl) I Nomenclature
ether (R-O-R’) I Alcohols, Ethers, Epoxides
ethyl acetate (EtOAc) I Solvents
ethyl ether (Et2O) I Solvents
ethyne (acetylene or HCCH) I Alkynes
evaporation GEN Lab also Vaporization
excess of reagent (“xs“); a non-limiting qnty. I Lab
excited state (*) I Molecular Orbitals
exergonic (-ΔG) I Kinetics and Thermodynamics
exothermic (-ΔH) I Kinetics and Thermodynamics
expanded octet/shell I Trends in the Periodic Table
extinction coefficient (e) I Spectroscopy
fatty acid II Fats and Lipids
fingerprint region I IR Spectroscopy
first-order coupling I NMR Spectroscopy
first order splitting I NMR Spectroscopy
Fischer esterification II Carboxylic Acid Derivatives
Fischer Projection I,II Representing Compounds; Stereochemistry
Five Zone Analysis II Drug Formulation Medicinal Chem.
fluorination II Reactions of Benzene
formal charge I Bonding and Hybridization
fractional distillation LAB
fragment Ion (formerly “daughter” ion) I Mass Spectrometry
fragmentation reaction I Mass Spectrometry
free radical I Radicals
Friedel-Crafts acylation II Reactions of Benzene
Friedel-Crafts alkylation II Reactions of Benzene
front-side attack II
fullerenes II Allotropes of Carbon
functional groups I Functional Groups
fused II Polycyclic Ring Systems
Gas Chromatography (GC) LAB
gauche I Conformational Analysis
geminal or (1,1) I Nomenclature
‘geometric’ isomers (obsolete referring to E/Z) I Isomerism, Nomenclature
Gibbs Free Energy (G) I Kinetics and Thermodynamics
Gibbs-Helmholtz equation I Kinetics and Thermodynamics
Gilman reagent  (R)2CuLi (lithium dialkyl cuprate) I Organometallics; Cuprates
glucose II Sugars
glutamic acid (Glu or E) II Peptides and Proteins
glutamine II Peptides and Proteins
glycerol (1,2,3-propanetriol) II Fats and Lipids
Glycine (Gly or G) II Peptides and Proteins
glycosidic bond/linkage II Sugars
Grignard Reaction II Carbonyl Compounds
Grignard Reagent, R-MgX I Organometallics
Grob Fragmentation II Named Reactions
ground state (GS) I Reaction Coordinate Diagrams
Guanine (G) II Nucleic Acids
1,2-hydride [1,2-H] shift I Carbocations
1H-NMR I NMR Spectroscopy
hv (Plank’s constant⋅wavelength) GEN Energy of a photon
H-Bond (hydrogen bond) I Intermolecular interactions
halide (Group VIIA substituent) I Functional Groups
haloalkanes (alkyl halides. R-X) I Functional Groups
haloarene (aryl halide, Ar-X) I Functional Groups
halogen I Trends in the Periodic Table
halogenation I,II Addition, Substitution
Hammond Postulate I Transition State Theory; RCD
Hard/Soft-Acid/Base (HSAB) Theory I Polar Reactions
Haworth projection (“hay-worth”) II Sugars
heat (enthalpy) of combustion I Kinetics and Thermodynamics
heat (enthalpy) of formation, Hf I Kinetics and Thermodynamics
heats of hydrogenation I Kinetics and Thermodynamics
hemiacetal (or hemiketal) II Ketones and Aldehydes
Henderson-HasselBalch equation GEN Acids and Bases
Henry’s Law GEN Partial Pressures
Hess’s Law GEN Heat summation
HETCOR LAB Advanced Spectroscopy
heteroatom I Functional Groups
heterocycle I Functional Groups
heterogeneous I Catalysis
heterolysis I Covalent Bonding
heterolytic bond cleavage I Transition State Theory
Highest Occupied Molecular Orbital (HOMO) I Molecular Orbitals
Histidine (His or H) II Amino Acids and Proteins
HMQC II NMR (Advanced)
HOAc = AcOH = acetic acid I Nomenclature
Hofmann degradation II Named Reactions
Hofmann elimination (anti-Zaitzev) II Named Reactions
Hofmann’s Rule (anti-Zaitzev) I Elimination
HOMO-LUMO Gap/energy I Molecular Orbitals
homogeneous I catalysis
homolysis I Covalent Bonds; Transition States
homolytic bond cleavage (homolysis) I Transition States
Hooke’s Law GEN
Hückel’s Rule (4n+2) II Aromaticity
hybridization (of orbitals) I Bonding and Hybridization
hydration I Electrophilic Addition
hydride (H: anion) I Redox Reactions
hydroboration I Electrophilic Addition
hydroboration-oxidation I Electrophilic Addition
hydrolysis II Carboxylic Acid Derivatives
hydronium ion, H3O+ I Acids and Bases
hydrophilic GEN Solvents
hydrophobic GEN Solvents
hydrophobic Effect GEN Solvents
hygroscopic LAB
hyperconjugation I Electron Delocalization
I or spin quantum number (±½) I Electron Configuration
imidazole (imid.) II Aromatics; Heterocycles
imine II Aldehydes and Ketones
immiscible I Solvent and Solutions
in silico GEN (in glass)
in situ I (during the reaction)
in vitro I (in a model system)
in vivo I (in a living system)
indole II Aromatics; Alkaloids; Heterocycles
inductive effects I Electron Delocalization
Infrared spectroscopy I IR Spectroscopy
infrared spectrum I IR Spectroscopy
inhibitor II Radical Reactions
initiation I Radical Reactions
initiator I Radical Reactions
integration I NMR Spectroscopy
intermediate I Reactive Intermediates
intermolecular I Reaction Dynamics
internal alkene I Alkenes
internal alkyne I Alkynes
intramolecular I Reaction Dynamics
inversion of stereochemistry/configuration I Stereochemistry
iodination I Electrophilic Addition & Substitution
Iodoform reaction II Ketones and Aldehydes
ion GEN
ionic bond GEN Bonding and Hybridization
ionization I  Bonding and Hybridization
i-Pr (isopropyl) I Nomenclature
ipso substitution II (Nucleophilic) Aromatic Substitution
IR (infrared) I IR Spectroscopy
isoelectronic I Organometallic Chemistry
isoleucine (Ile or I) I Amino Acids and Proteins
isomer I Isomerism
isomerization I Isomerism
isotope I Mass Spectrometry
IUPAC (Int’l Union of Pure & Applied Chemistry) I Nomenclature
Jahn-Teller Effect I Advanced Organic
Joule (J) or kilojoule (kJ) GEN
Jones Reagent (acidic dichromate) II Redox Reactions
Ka (acid dissociation constant) I Acids and Bases
kcal / kilocalorie or Calorie (C = 1000cal) I Equilibrium
kJ / kilojoule I Equilibrium
Kekulé structure I Representing Organic Compounds
Keq (equilibrium constant) GEN Equilibrium
keto isomer form I Tautomerism/Tautomerization
ketone II Ketones and Aldehydes
ketose II Sugars
ketoxime II Sugars
Kinetic Control/Product I Kinetics & Thermodynamics
l- (prefix) I Stereochemistry
L- (prefix) I Stereochemistry
lactam II Carboxylic Acid Derivatives
lactone II Carboxylic Acid Derivatives
late transition state I The Transition State
LDA (lithium diisopropylamide) II Ketones and aldehydes
Le Chateliér’s Principle GEN
leaving group I Substitution; Elimination
Leucine (Leu or L) II Peptides and Proteins
levorotatory (L or l or -) I Stereochemistry
Lewis acids & bases; definition I Acids and Bases
Lewis dot structure I Bonding and Hybridization
Lewis structure I Bonding and Hybridization
ligand I Hybridization; Organometallics
limiting reagent LAB
lipid II Fats and Lipids
lipophilic (aliphatic) II Fats and Lipids
lipophobic (hydrophilic) II Fats and Lipids
London (dispersion) forces I Intermolecular Forces
lone pair (electrons) I Bonding and Hybridization
long-range coupling I NMR Spectroscopy
Lowest Unoccupied Molecular Orbital (LUMO) I Molecular Orbital Theory
Lysine (Lys or K) II Amino Acids and Proteins
µ (mu) I Dipole Moment
M+ (molecular ion) I Mass Spectrometry
M+1 I Mass Spectrometry
M+2 I Mass Spectrometry
m/z (units of Mass Spectrometry) I Mass Spectrometry
main group elements (A group) I Trends in the Periodic Table
major groove II Nucleic Acids
Markovnikov Regiochemistry I Electrophilic Addition
Markovnikov’s Rule I Electrophilic Addition
mass spectrum I Mass Spectrometry
mass spectrometry I Mass Spectrometry
McLafferty Rearrangement I Mass Spectrometry
mCPBA I Redox Reactions
Me- (methyl) I Nomenclature
mechanism (re reactions) I Arrow Pushing and Mechanism
medicinal chemistry II Medicinal Chemistry
melting point (MP) LAB
mercaptan (thiol) I Sulfur Compounds
meso compound/diastereomer I Stereochemistry
mesomerism (see resonance) I Stereochemistry
mesylate (-OMs) I Substitution
meta- (1,3-) I Reactions of Benzene
meta director/directing II Reactions of Benzene
metals and metalloids I The Periodic Table
metabolism II Biochemistry
methanesulfonate I Substitution
methanesulfonic acid I Substitution
methine proton R3C-H I NMR Spectroscopy
Methionine (Met or M) II Peptides and Proteins
methylene group R2CH2 I NMR Spectroscopy
microscopic reversibility, principle of I Rxn Coord Diagrams
mineral acid I Acids and Bases
minor groove II Nucleic Acids
miscible I Solutions & Solvents
moiety I Functional Groups
mol Gen  mole
molar mass / molecular weight Gen
mole (Avagadro’s Number of species) Gen
molecular formula (CnHm….) Gen Alkanes
molecular ion (M+); formerly “mother” ion I Mass Spectrometry
molecular model kit I Blog; Adjusting to organic chemistry
molecular sieve (MS) (3Å-4Å) LAB
molecular weight (MW or M) or molar mass GEN
molozonide I Redox reactions; Alkenes
molecular orbital (MO) I Molecular Orbitals
monosubstituted I Alkenes
multiplet (m) I NMR Spectroscopy
mutarotation II Sugars; Epimerization
N-bromosuccinimide (NBS) I Electrophilic Addition, Radicals
N-chlorosuccinimide (NCS) I Electrophilic Addition
N-iodosuccinimide (NIS) I Electrophilic Addition, Radicals
n-  (normal or unbranched) I Nomenclature
n-BuLi I Alkanes; Organometallics
n+1 rule I NMR Spectroscopy
4n rule II Aromaticity
4n+2 (Hückel’s rule) II Aromaticity
NaBH4 I Redox Reactions
NaH I Substitution; Alcohols
Named Reaction I Named Reactions
Natural Product  (Organic I, Intro to Synthesis) II Organic Subdivisions; Synthesis
Newman Projection I Conformational Analysis
nitration (-NO2) II Reactions of Benzene
nitrile II Carboxylic Acid Derivatives
nitro compounds/groups II Reactions of Benzene, Amines
nitrogen/amine (Walden) inversion I Stereochemistry
“Nitrogen Rule” I Mass Spectrometry
NMR I Nuclear Magnetic Resonance
node or nodal surface I Atoms and Orbitals
nomenclature I IUPAC Nomenclature
Non-first Order Coupling I NMR Spectroscopy
Non-first Order Splitting I NMR Spectroscopy
non-aromatic II Aromaticity
non-bonded electron pair I Mass Spectrometry
non-decoupled II C NMR Spectroscopy
nonpolar nolvent II Solvents
non-spontaneous reaction I Kinetics vs. Thermodynamics
nonsuperimposable (unmappable on itself) I Chirality
Nu: (nucleophile) I Reaction Mechanism, Lewis Bases
nuclear spin flip I NMR Spectroscopy
nucleic acids II Nucleic Acids
nucleophile I Reaction Mechanisms
Nucleophilic Aromatic Substitution II Reactions of Benzene II
nucleophilicity I Reaction Mechanism
nucleoside II Nucleic Acids
nucleotide II Nucleic Acids
Octet Rule (second row elements) I Bonding and Hybridization
olefin (alkene) I Alkenes
one equivalent (1 equiv.) (1eq.) LAB
One-Molecule-Rule I
optical activity I Chirality & Stereochemistry
optically inactive I Chirality & Stereochemistry
organometallic (organotransition metals) I Organotransition metal compounds
organolithium Reagent, RLi I Organometallics
ortho– (o-) II Reactions of Benzene
ortho/para directing group II Reactions of Benzene
-OMs (mesylate) I Alcohols
-OTf (triflate) I Alcohols; Amines, Oximes
-OTs (tosylate) I Alcohols
oxaphosphetaine II Ketones & Aldehydes
oxidant/oxidizing agent I,II Redox Reactions
oxidation I,II Electrophilic Addition, Redox
oxime II Ketones and Aldehydes
oxonium ion; oxocarbenium ion II Alkenes, Ketones and Aldehydes
oxyanion I Substitution
ozone (O3) I Redox Reactions, Alkenes, Alkynes
ozonolysis (Harries Reaction) I Redox Reactions, Alkenes, Alkynes
pi-(π) bond I Bonding and Hybridization
pi-(π) molecular orbital I Bonding and Hybridization
pi* (π*) molecular orbital I Bonding and Hybridization
p orbital / p character I Bonding and Hybridization
para- (1,4-) II Reactions of Benzene
paraffin I Alkanes
pentet I NMR Spectroscopy
peptide II Amino Acids and Proteins
peptide (amide) bond II Amino Acids and Proteins
peracetic acid (RCO3H) I Redox Reactions
peracid I Redox Reactions
percent (%) yield (Actual Yield) LAB
permanganate I Redox Reactions
peroxide (ROOR), peracid (RCO3H) I Radical Reactions
pH I Acids and Bases
pKa I Acids and Bases
pharmacology; pharacokinetics II Drugs and Enzymes
phenol  (Organic II, Reactions of Benzene) II Alcohols; Reactions of Benzene
phenyl group (Ph-) I Nomenclature
Phenylalanine (Phe, F) II AminoAcids and Proteins
phospholipid II Fats and Lipids
phosphodiester II Nucleic Acids
photochemistry II Pericyclic Reactions
photolysis II Radical Reactions
photon (E = hv) Gen
pi-cation interaction II Secondary Spatial Effects
π-stacking II Secondary Spatial Effects
piperidine II Heterocycles
pKa I Acids and Bases
pKb I Acids and Bases
plane-polarized light I Chirality
polar covalent bond I Bonding and Hybridization
polar polvent I Solvents
polarimetry I Chirality
polarizability GEN
polypeptide II Peptides and Proteins
polysaccharide II Sugars
potential energy I Kinetics and Thermodynamics
ppm I NMR Spectroscopy
Pr- (propyl substituent) I Nomenclature
precipitate LAB
primary (1o) I Classifying Carbons
pro-drug II Drugs and Enzymes
product I Mechanism
Proline (Pro or P) II Peptides and Proteins
propagation I Radical Reactions
progargylic position I Resonance
Protection, Functional Group I Ketones and aldehydes
protecting groups II Protecting Groups
protein II Peptides and Proteins
protic solvent (H-bonding solvent) I Solvents
proton (H+) I Atoms and Molecules
proton 1H NMR I NMR Spectroscopy
protonation I Catalysis
p-toluenesulfonate I Substitution/Elimination
p-TsCl (para-toluenesulfonyl chloride) I Substitution/Elimination
p-TsOH (para-toluenesulfonic acid) I Substitution/Elimination
purine II Nucleic Acids
pyran II Alcohols, Ethers & Epoxides
pyridine (pyr.) II Aromatics
pyrimidine II Nucleic Acids
pyrrole II Aromaticity; Heterocycles
pyrrolidine II Heterocycles; Amines
QSAR (quantitative structure-activity relationships) I Electron Configuration
quantum numbers I Electron Configuration
quartet (q) I NMR Spectroscopy
quaternary Carbon (4o) I Classifying Carbon
quaternary structure I Peptides & Proteins; Enzymes
quintet I NMR Spectroscopy
R  = Universal Descriptor I Nomenclature
R- Group (often alkyl) I Nomenclature
racemic I Stereochemistry
racemic mixture (racemate) I Stereochemistry
radical or free radical I Radicals
radical cation I Mass Spectrometry
rate-determining or rate-limiting or slow I Rxn Coord Diagrams
reactant I Mechanism
reaction coordinate diagram I Rxn Coord Diagrams
reaction coordinate (surface) I Mechanism
reaction mechanism I Organic Reactions
reactive oxygen species (ROS) I Radicals
reactivity-selectivity principle I Kinetics & Thermodynamics
rearrangements (as reactions) I, II Carbocations
reducing agent or reductant I Redox Reactions
reduction (reaction) I Redox Reactions
regioselectivity, regioselection I Regiochemistry
resolution – chiral; kinetic I Stereochemistry
resonance I Resonance I
resonance contributor/structure/mesomer I Resonance I
resonance forms, prioritization of I Resonance I
Retro-aldol II Ketones & Aldehydes
Retro Diels-Alder ([4+2] cycloreversion) I Dienes
Retrosynthetic Analysis/Retrosynthesis I Introduction to Synthesis
Ribonucleic Acid II Nucleic Acids
ribose II Nucleic Acids
Ring Flip – Chair-Boat-Chair Interconversion I Conformational Analysis
Ring Strain: Baeyer, Pitzer, Transannular I Conformational Analysis
RNA – ribonucleic acid II Nucleic Acids
sigma (σ) bond I Bonding and Hybridization
s orbital I Bonding and Hybridization
σ and σ* orbitals I Bonding and Hybridization
S (Lat. sinister) configuration I Stereochemistry
s-cis   (s = single-bond) I Dienes
s-BuLi (s=sec) II Carbon Bases
s-trans (s = single-bond) I Dienes
Sanger’s Reagent II Nucleic Acid (Sequencing)
saponification (ester hydrolysis) II Carboxylic Acid Derivatives
saturated I Alkanes
sawhorse projection I Representing Organic Compounds
Saytseff’s Rule (Zaitzev’s Rule) I Elimination
Schiff Base (akylamine) II Ketones and Aldehydes
sec-butyl group I Nomenclature
secondary structure II Peptides and Proteins, Nucleic Acids
Serine (ser or S) II Peptides and Proteins
sextet I NMR Spectroscopy
side chain I Nomenclature
shielded (upfield), chemically I NMR Spectroscopy
single bond I Bonding and Hybridization
singlet (s) I NMR Spectroscopy
skeletal formula (line-angle) I Representing Organic Compounds
SN1 limiting mechanism I Substitution
SN2 limiting mechanism; SN2′ mechanism I Substitution
sodium borohydride (NaBH4) I Redox Reactions
sodium hydride (NaH) I Bases
solubility I Solvents
solute I Solvents
solvent I Solvents
solvent cage I Solvents
solvolysis/solvolytic I SN1 and E1
sp orbitals/atoms I Hybridization
sp2 orbitals/atoms I Orbital Hybridization
sp3 orbitals/atoms I Orbital Hybridization
space-filling model I Representing Organic Compounds
specific rotation [αo] I Chirality
spectrometry I Structural Elucidation
spectroscopy I Structural Elucidation
spin quantum number I Electron Configuration
spin-spin coupling I Spectroscopy
spirocyclic ring II Polycyclic rings systems
splitting, nuclear (multiplicity in signals) I NMR Spectroscopy
spontaneous change/reaction I Thermodynamics
squiggly line bond I Representing organic compounds
staggered conformation I Newman Projections
starting material (substrate beginning a synthesis) I Reactions
stereocenter or stereogenic center I Chirality
stereochemistry I Stereochemistry
stereoselective I Chirality
stereospecific I Stereochemistry
steric effects I Stereoelectronics
steric hindrance I Conformational Analysis
steric number I Conformational Analysis
steric strain I Conformational Analysis
steroids II Lipids and Fats
stoichiometry GEN
stretching frequency [cm-1] I IR Spectroscopy
sublimation GEN (s) → (g)
substituent (any replacement for hydrogen) I Nomenclature
substitution Reaction (displacement) I Classes of reaction
substrate (reactant) I Mechanism
sucrose (disaccharide) II Sugars
suicide inhibitor/inhibition II Drugs, Enzymes, & Kinetics
sulfide (R-S-R) I Functional Groups
sulfonamide (-S(O2)ONR2) II Functional Groups
sulfonate ester (RSO3R) I Functional Groups
sulfonate anion (-RSO3-) I Functional Groups
sulfonic acid (RSO3H) I Functional Groups
sulfonation II Reactions of Benzene
sulfone (R-SO2R) I Functional Groups
sulfonic Acid II Functional Groups
sulfonyl chloride (thionyl chloride) II Substitution
sulfoxide (R-S(O)R) I Functional Groups
superimposable (superposable or mappable onto itself) I Chirality
suspension GEN
symmetric stretch I IR spectroscopy
syn or erythro configuration (rings or chains) I Modes of Addition
syn addition I Modes of Addition
syn-periplanar I Dihedral geometry
synthesis I Chemical Synthesis
t-BuLi II Organometallics
tautomer I Tautomerization
tautomerization I Tautomerization
t-Bu I tert-butyl
t-BuOH I t-butyl alcohol
terminal alkene I Alkenes
terminal alkyne I Alkynes
termination, of a chain reaction I Radical Reactions
termolecular (3rd order) I Electrophilic Addition
tertiary (3o I Classifying carbon
tetrahedral carbon (sp3 I Classifying carbon
tetrahedral intermediate I Carboxylic Acid Derivatives
tetrahydrofuran (THF) I Solvents
tetramethylsilane (TMS) I NMR Spectroscopy
tetrasubstituted I Alkene stability
theoretical yield GEN Lab
thermodynamic control/product I Kinetics vs. Thermodynamics
thioester I Functional Groups
thioether (sulfide, R-S-R’) I Functional Groups
thiol (thioalcohol; RSH; mercaptan) I Functional Groups
thiolate anion; RS I Functional Groups
thiophene I Heterocycles
Threonine (Thr or T) II Peptides and Proteins
Thymine (T) II Nucleic Acids
titration I Acids and Bases
toluene (tol.) I Aromaticity
torsional strain I Conformational Analysis
tosylate (-OTs) I Substitution
trans I Stereochemistry
transesterification II Carboxylic Acid Derivatives
transition metals II Organometallics
transition state I Reaction Mechanism
tricyclic I Polycyclic compounds
triflate (-OTf) I Super Leaving groups
triflic acid (HOTf, TfOH) I Substitution
triglyceride (Triacylglycerol) II Fats and Lipids
triose II Sugars
triple bond I Alkynes
triplet (t) I NMR Spectroscopy
triplet of doublets (td) I NMR Spectroscopy
trisubstituted I Alkenes
Tritium 3H I Mass Spectrometry
Tryptophan (Trp or W) II Peptides and Proteins
Two-Dimensional NMR II NMR spectroscopy
Tyrosine (Tyr or Y) I Peptides and Proteins
unimolecular kinetics I Kinetics
unsaturated / unsaturation I Fats and Lipids
upfield, chemically (shielded) I NMR Spectroscopy
Uracil (U) II Nucleic Acids
valence I Trends in the Periodic Table
Valence Bond Theory I Theory
valence electrons I Electron Configuration
valence shell I Electron Configuration
Valine (Val or V) I Peptides and Proteins
Van der Waals Forces I Intermolecular Interactions
Van ’t Hoff Rule I Stereochemistry
vapor pressure LAB
vaporization GEN
vicinal (1,2 or vic) I Nomenclature
vinyl group I Nomenclature
vinylic Position I Nomenclature
vitamin II Enzymes and Co-factors
VSEPR Guidelines GEN
Walden Inversion I Stereochemistry
Watson-Crick Base Pair II Nucleic Acids
wavenumber (cm-1) I IR Spectroscopy
wavy line (ambiguous configuration) I Representing Organic Compounds
wedge I Representing Organic Compounds
Williamson Ether Synthesis I Named Reactions
Wittig Reaction II Ketones and Aldehydes
Wolff-Kischner Reduction II Redox Reactions
% percent yield (actual yield) LAB
ylide (or ylid) II Ketones and Aldehydes
 Z (Ger. Zussamen) olelins, esters, enolates I Stereochemistry
Zaitsev’s Rule I Elimination
zig-zag Structure (see line-angle) I Drawing Organic Structures
 zwitterion (‘w’ pronounced as ‘v’) II Peptides and Proteins



Organic-ese Organic Chemistry



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