A-values
of cyclohexyl substituents
abietic acid
absolute configuration
acetals
acetoacetic ester alkylation
acceptor reactant in the aldol reaction
achirality
achiral diastereomers
aci-anions
from nitroalkanes
acid-base catalysis
(supplemental material)
acid-base equilibria
acidic and basic resolving agents
acidity constant Ka
acidity
equilibrium acidity
solvent effects on pKa s
carbon acids
α hydrogens
stereoelectronic factors in enolization
carboxylic acids
inductive effects
resonance effect
stabilization of carboxylate anion
substituent effects
advanced treatment
kinetic acidity
base catalyzed isotope exchange
of nitroalkanes
structural reorganization factor
hybridization
super acid
activating substituents
activation energy
activation enthalpy
and
transition state
acyl anion equivalent
acylation reactions
specialized acylation reagents
(supplemental material)
acyl carbene rearrangements
acyl nitrene rearrangements
acyloin condensation
acyloins from thiazolium catalyzed aldehyde condensations
addition reaction defined
addition reactions of allenes
1,2 & 1,4-addition to dienes
addition reaction example
addition reactions of alkenes
addition reactions of benzene
addition reactions of alkynes
addition to cyclopropane
alcohols
nomenclature
reactions
dehydration
oxidation
substitution of hydroxyl hydrogen
nucleophilic substitution of OH
by hypervalent phosphorous reagents
(supplemental material)
by way of sulfonate esters
Williamson ether synthesis
alcoholysis
aldehydes
see carbonyl compounds
the aldol reaction
diastereoselectivity
directed aldol reactions
enantioselectivity
enolborinate intermediates
enamine aldol
interacting substituent effects
Mukaiyama aldol
stereoselective synthesis
transition state
aldoses
see carbohydrates
aliphatic
alkali metals
alkaloids
alkane nomenclature
alkene configurational isomers
alkene/alkyne nomenclature
alkene reactions
addition of Brønsted acids
allylic substitution
halogen additions
hydration
hydrogen addition
hydroboration
hypohalous acid additions
Lewis acid additions
oxidative additions
oxymercuration
ozonolysis
radical additions
radical polymerization
stereoselectivity of addition
hydroboration stereoselectivity
alkyl groups
alkyl halide reactions
reaction variables
nucleophilic substitution
alkyl group influence
cation effects
(supplemental material)
molecularity
nucleophilicity
S
N
2 mechanism
S
N
1 mechanism
solvolysis
solvent effects
steric hindrance
(
animation
)
beta-elimination
anti-stereospecificity
beta-hydrogen requirement
Bredt's rule
E1 mechanism
E2 mechanism
the Zaitsev rule
summary comparison of halide reactions
formation of organometallic compounds
alkyl lithium reagents
alkylation of stabilized enolate anions
alkyne reactions
acidity of terminal alkynes
addition of nucleophiles
hydration
hydroboration
hydrogen addition
oxidation
preparation from dihalides
reduction by sodium in ammonia
allenes
allotropes of carbon
allyl group
allyl radical
allylic Grignard addition
allylic halogenation
allylic strain
1,2 & 1,3
alpha effect
(supplemental material)
ambident anions
amide basicity
amines
natural compounds
nomenclature
primary, secondary & tertiary
amine oxides
nitroxide radicals
preparation of 1º-amines
preparation of 2º & 3º-amines
properties
acidity
basicity
boiling points & solubility
reactions
amine oxide elimination
aryl amines & nitrous acid
Cope elimination
the Hinsberg test
Hofmann elimination
reaction with nitrous acid
substitution at nitrogen
substitution & elimination of nitrogen
structure-formula relationship
extended to N-compounds
amino acids
see proteins
aminolysis
amphiphilic & amphipathic
amphoterism
amylose
anandamide
anchimeric assistance
angle strain
anion solvation
(supplemntal material)
anion stability order
(supplemental material)
anionic rearrangements
anisotropy
annulenes
anomers
see carbohydrates
anomeric effect
antarafacial
& suprafaciaL
anthracene
anti conformer
anti-syn stereo nomenclature
(supplemental material)
anti-syn addition
antiaromaticity
Arndt-Eistert reaction
(supplemental material)
aromatic stabilization
aromaticity
aromaticity factors
aromatic 5-membered heterocycles
aromatic 6-membered heterocycles
arrows, use of different kinds
aryl diazonium salts
substitution reactions
coupling reactions
Arndt-Eistert synthesis
asymmetric carbon
asymmetric induction
asymmetry
atomic orbitals
atomization energy
atropine
atropisomers
(supplemental material)
aufbau principle
axial
azacations
aziridine inversion
the Baldwin rules
Barton reaction
base pairing
basicity, Brønsted defined
basicity, Lewis defined
basicity of amines
of pyridines and related heterocycles
basicity of amides
basic reagents
basicity & nucleophilicity
(supplemental material)
basicity & solvent effects
Baeyer-Villiger rearrangement
Beckmann rearrangement
Benedict's test
benzene derivative nomenclature
benzene molecular orbitals
(
animation
)
benzene
electrophilic substitution reactions
mechanism of electrophilic substitution
(
animation
)
halogenation, nitration, sulfonation, Friedel-Crafts
addition reactions
elimination reactions
nucleophilic substitution reactions
benzene derivatives-substituent effects
substitution orientation
correlation of reactivity and orientation
disubstituted benzenes
halobenzene conversion to organometallic compounds
hydrolysis of aryl sulfonic acids
modifying substituent influence
oxidation of alkyl side-chains
Birch reduction
reduction of nitro groups & aryl ketones
benzenonium ion
benzoin condensation
benzyl group
benzyl radical
benzylic acid rearrangement
benzyne
beta-elimination
betaine
bicyclic compounds
bilirubin photochemistry
biosynthetic pathways
biotin
biphenyl stereoisomers
(supplemental material)
Birch reduction
boat conformer
boiling point
bond dipole
bond dipoles and molecular dipole
bond energy
average bond energy
bond dissociation energy of C-H
bond energy and radical stability
(supplemental material)
bond-breaking
bond-making
p-d double-bonding
borane (diborane)
Bredt's rule
(supplemental material)
bridged ring compounds
bromination
bromonium ion intermediate
Brønsted theory
Brook rearrangement
buckminsterfullerene
Bürgi-Dunitz trajectory
butane conformers
C
60
cage effect in radical reactions
caffeine
Cahn-Ingold Prelog notation
examples
in morphine, strychnine & taxol
camphor
Cannizzaro reaction
canonical structures
cantharidin
carbanion
carbanion stability
carbene
carbenoid
carbocation
stabilization by inductive, resonance & hyperconjugation effects
carbocation stability order
nonclassical carbocations
carbocation rearrangement
stable carbocations
tropylium & trityl
carbodiimides
carbohydrates
aldaric acid
aldonic acid
aldose
anomeric effect
anomers
cyclodextrins
D-configuration
disaccharides
cellobiose, maltose & sucrose
furanose & pyranose forms
glucose
anomeric forms
cyclic forms
structure proof
glycosides
α & β-anomers
glycon & aglycon
Haworth formulas
ketoses
Kiliani-Fischer synthesis
osazone formation
oxidation
polysaccharides
cellulose
cellulose acetate & nitrate
rayon
hemicellulose
starch
amylopectin
amylose
Ruff degradation
tri- & higher oligosaccharides
vitamin C
carbon atom classification
(1º, 2º, 3º & 4º)
Carbonyl Compounds
aldehydes & ketones
addition reactions (reversible)
acetal formation
cyanohydrins
enamine formation
imine formation
(
animation
)
water or alcohol
addition reactions (irreversible)
metal hydrides
organometallic reagents
R-Li & R-MgX
stereoselectivity of addition
in acyclic compounds
1:2-diastereoselectivity
chelation effects
1:3-diastereoselectivity
polar non-chelation effects
conjugate addition reactions
(supplemental material)
deoxygenation (reduction)
Wolff-Kishner
Clemmensen
thioacetal hydrogenolysis
derivatives
more derivatives
(supplemental material)
enantioselective reduction
natural compounds
nomenclature
oxidation
preparation
properties
reactions at the α-carbon
the aldol reaction
crossed or mixed aldol reactions
dehydration of aldol products
electrophilic substitution
the ambident character of enolate anions
alkylation
reducing agent summary
stable hydrates & hemiacetals
(supplemental material)
ylide reactions
(supplemental material)
carbonyldiimidazole
carboxylic acids
acidity
inductive effects
resonance effect
stabilization of carboxylate anion
substituent effects
(supplemental material)
derivatives
nomenclature
physical properties
reactions
:
acyl substitution
,
reduction
,
organometallic reagents
,
reactivity & IR stretching frequency
(supplemental material)
summary of reducing agents
(supplemental material)
reactions at the α carbon
:
Claisen & Dieckmann condensations
fatty acids
natural compounds
nomenclature
physical properties
preparation
reactions
decarboxylation
esterification
oxidations
reduction
salt formation
substitution of the hydroxyl hydrogen
substitution of the hydroxyl group
β-carotene
carvone
catalyst
acid-base catalysis
(supplemental material)
catalysis of the aldol reaction
catalytic hydrogenation
Lewis acid catalysis of cycloadditions
structure of Sharpless epoxidation catalyst
cation rearrangements
cellulose
see carbohydrates
central dogma
chain reaction
chain reaction in bromination
(
animation
)
chair conformer
chelation effect in stereoselectivity of carbonyl additions
cheletropic addition
of SO
2
chemical reaction
(defined)
chemical stability
Chichibabin reaction
chirality
center
nomenclature of
axial
helical
planar
chiral auxiliary
chloral & chloral hydrate
chlorination of alkanes
chocolate polymorphs
cholesterol
cholic acid
chromophore
chrysene
Chugaev reaction
C.I.P. system
citral
citric acid
cis/trans notation
Claisen condensation
Claisen rearrangement
Claisen Schmidt reaction
Clemmensen reduction
cocaine
combustion
heat of
competitive electronic effects
inductive & resonance
condensation reactions
condensed formulas
configuration
of chiral centers
of chiral axes
of chiral planes
configuration of radicals
configuration inversion of amines
in aziridines
configurational notation at chiral centers
lactic acid & carvone
morphine, strychnine & taxol
conformational isomers
conformational analysis principles
conformational enantiomers
biphenyl conformations
(supplemental material)
cyclohexane conformations
cyclohexene conformations
s-cis & s-trans conformers of dienes
conglomerate solid
conjugate acid/base pairs
coniine
conjugated dienes
conjugate addition reactions
conrotatory
constitutional isomers
Cope elimination
Cope Rearrangement
corannulene
Corey-Winter reaction
corn syrup
coronene
cortisone
Couper-Kekulé formula
coupling constants for
1
H nmr
covalent bonding
Cram's rule for acyclic diastereoselectivity
crotyl Grignard reagent
diastereoselectivity of addition reactions
crotyl boron reagents
enantioselectivity of addition reactions
crown ethers
cumulated dienes
Curtin-Hammett Principle
Curtius rearrangement
curved arrows
use in writing mechanisms
cyanohydrin
cyclic halonium ion intermediates
cyclic mercurium ion intermediates
cyclic sulfonium ion intermediates
cyclization vs. dimerization
cycloaddition
[2+2] & [4+2] cycloaddition
stereospecificity of cycloaddition
pericyclic character
cycloalkanes
cycloalkane configurational isomers
cycloalkane conformers
cycloalkane nomenclature
cyclooctatetraene
cyclohexane conformations
discussion
cyclohexene conformations
cyclopropanation of alkenes
cyclopropane addition reactions
cycloreversion
dashed or hatched bonds
DBU
1,8-diazabicyclo[5.4.0]undec-7-ene
deactivating substituents
dealkylation of esters
deamination of 1º-amines
decalin conformations
decarboxylation of carboxylic acids
dehydration of 1º-amides to nitriles
derivatives of carboxylic acids
nomenclature
physical properties
reactions
acyl substitution
reduction
organometallic reagents
reactions at the α carbon
:
Claisen & Dieckmann condensations
dextrorotatory
diamond structure
diastereomeric excess
diastereomers
diastereoselectivity
in halogen addition to C=C
in nucleophile addition to C=O
diastereoselectivity
diastereotopic
diazo ketone reactions
diborane (borane)
dicyclohexylcarbodiimide
DCC
Dieckmann condensation
dielectric constant
Diels-Alder reaction
[4+2] cycloaddition
endo effect
[regioselectivity
suprafacial character
entropy & free energy change
dienes
isolated, conjugated & cumulated
addition reactions of dienes
conjugated dienes
molecular orbital model (
animation
)
Diels-Alder reactions of dienes
endo & exo stereospecificity
suprafacial stereospecificity
diene stability
heats of hydrogenation
s-cis & s-trans conformations
dienophile
diethyl malonate or malonic ester
dihalide reactions
dihedral angle
diimide
diisobutylaluminumhydride
DIBAH
dinitrophenylhydrazone
DNP derivatives
dimethylsulfonium methylide
dimethyl sulfoxide oxidation of alcohols
dimsyl sodium
dipole
dipolar cycloadditions
disaccharides
see carbohydrates
disiamylborane
(in hydroboration of alkynes)
disrotatory
dissolving metal reductions
aromatic rings
carbonyl compounds
(supplemental material)
conjugated π-electron systems
dissymmetry
DMAP
4-dimethylaminopyridine
an acyl transfer agent
DNA
secondary structure of
replication of
donor reactant in the aldol reaction
Dötz reaction
double helix
dye pigments: natural
dye pigments: synthetic
dynamic kinetic resolution
E/Z notation
eclipsed conformer
eclipsing strain
also see torsional strain
electrocyclic reactions
electronegativity
electrophile
electronic excited state
electrophilic substitution of benzene
of 5-membered heterocycles
of 6-membered heterocycles
electrophoresis
elimination reaction example
elimination reactions
E2 elimination
pyrolytic syn-eliminations
enamide bases
enamines
enantiomers
enantiomeric excess
enantiomorphism
enantiotopic atoms or groups
enantiotopic faces
enantioselectivity
endergonic
endo / exo terminology
endothermic
ene reactions
intramolecular reactions
elimination reactions
energetics of reactions
energy
kinetic & potential
enthalpy
free energy
energy of activation
enol tautomer
electrophilic substitution of
solvent dependence in dicarbonyl compounds
enolate anion
the ambident character of enolate anions
concentrations in water solution
configuration (E & Z)
aldol diastereospecificity of
stereoselective formation
β-dicarbonyl compounds
O vs. C-reaction
regioselectivity of enolate anion formation
surrogates for enolate anions
enamines
imine conjugate bases
enamide bases
silyl enol ethers
enthalpy
entropy
ephedrine
epimer
epoxides
& epoxidation
stereoselectivity of epoxidation
Sharpless enantioselective epoxidation
epoxide reactions
intramolecular epoxide opening
EPR
electron paramagnetic resonance
equatorial
equilibrium arrow
equilibrium-free energy relationship
erythro-threo notation
(supplemental material)
ESR
electron spin resonance
Eschenmoser's salt
esterification
ester cleavage
(supplemental material)
ester pyrolysis
ethane conformers
ethers
nomenclature
preparation
Alkoxymercuration & Williamson
reactions
used as protective groups
(supplemental material)
silyl ethers
(supplemental material)
ethyl acetoacetate or acetoacetic ester
ethylogy & ethylagous reactions
eutectic point
exergonic
exo / endo terminology
exothermic
fats & oils
see lipids
fatty acids
oleic and stearic acid
unusual fatty acids acid
Favorskii rearrangement
Fehling's test
Felkin-Ahn rule for acyclic diastereoselectivity
ferrocene
Fischer carbenes
Fischer esterification
Fischer indole synthesis
Fischer projection formula
fluorocarbon reactivity
formal charge
formula analysis
free energy
Gibb's free energy
free energy of activation
free radical reactions
free radical bromination (
animation
)
Fremy's salt
frequency
Friedel-Crafts alkylation & acylation
functional groups defined
functional group nomenclature
(supplemental information)
functional group reactivity
fullerenes
fused ring compounds
fused benzene ring compounds
galvinoxyl
gauche conformer
geminal
Gilman reagents
reaction with acyl chlorides
glucose
see carbohydrates<
glycans
glycols
glycol cleavage
glycosides
see carbohydrates
Gomberg, Moses
graphite structure
Grignard reagents
Grob fragmentation
Grubbs metathesis catalysts
guanidine
gutta-percha
haloform reaction
halogenation of alkanes
halogenation of benzene
halogens
the Hammett equation
Hammett sigma constants
Hammett rho constants
the Hammond postulate
Hantzsch-Widman nomenclature
hatched bonds
heat of combustion
heat of formation
heat of hydrogenation (benzene)
heat of hydrogenation (alkenes)
Heck reaction
helminthosporal
hemicellulose
Henderson-Hasselbach equation
heterocyclic compounds
nomenclature
nomenclature examples
three-membered rings
four-membered rings
five-membered rings
six-membered rings
heterolysis
heterotopic
hexahelicene
hexamethylenetetramine
Hinsberg test
Hofmann elimination
Hofmann rearrangement
1º-amine preparation
(supplemental material)
the Hofmann rule
homology
homolysis
thermal
photochemical
homoenolate
homotopic
honey
Horeau's method
Horner-Wadsworth-Emmons reaction
hula-twist isomerization
Hunsdiecker reaction
Hückel rule
Hünig's base
hybrid orbitals
hybridization states of carbon
hybridization & acidity
hydrazone
hydride transfer reduction
(supplemental material)
hydroboration
stereoselectivity of
hydrogen bonding
hydrogen bond acceptor
hydrogen bond donor
hydrogenation
hydrogenation of alkenes
hydrogenation of alkynes
hydrogenation of benzene
hydrolysis
hydrophilic
hydrophobic
hydroxylation
hydroxyl group substitution by hypervalent phosphorous reagents
hyperconjugation
hypervalency
hypohalous acids
imine formation
(
animation
)
indole, reactions of
inductive effect defined
inductive effect and acidity
inductive effect of benzene substituents
inert gases
infrared spectroscopy
see Spectroscopy
insulin
in model display
intramolecular reactions
compared with intermolecular reactions
intermolecular forces
inversion of configuration in amines
in aziridines
invert sugar
iodoform test
iodolactone formation
ion solvation
of ions
ionic bonding
ionic reactions
ionization potential
(of alkenes & alkynes)
isoelectric point
(pI)
isomer relationship chart
isomers of disubstituted cyclohexanes
isomers
evidence for structural formulas
different properties of
Jones reagent
Karabatsos rule for acyclic diastereoselectivity
Kekulé-Couper formula
kekulene
ketene
keto tautomer
ketones
see carbonyl compounds
ketyls
kinetic energy distribution
kinetics
and
reaction rate
kinetic order
kinetic vs. equilibrium control
enolate anion formation
diene additions
semicarbazone formation
(supplemental material)
kinetic acidity
kinetic resolution
kinetic resolution of racemic amino acids
Kolbe-Schmidt reaction
lactam
lactic acid
lactone
alpha-lactone
beta-lactone
lactonization
of unsaturated acids
iodolactonization
LD
50
LDA
lithium diisopropylamide
lead tetraacetate & glycol cleavage
Leuckart reaction
(supplemental material)
levorotatory
Lewis acids
(and bases)
Lewis formula
Lindlar's catalyst
(for selective reduction of alkynes)
linear configuration
linear free energy relationships
lipids
biosynthesis
fats & oils
fatty acids
arachidonic, lauric, linoleic, oleic, palmitic, stearic
unusual fatty acids
lipidic vitamins
A, D, E, K
phospholipids
liposome
planar bilayer
prostaglandins & other eicosanoids
steroids
cholesterol & cholic acid
conformations of decalin
terpenes
isoprene rule
mevalonate & dxp paths
polyisoprenoids
rubber & gutta-percha
triglycerides
soaps & detergents
amphipathic or amphiphilic
micelles
surfactant
waxes
lithium aluminum hydride
LAH
lithium diisopropylamide
LDA
lithium tri-tert-butoxyaluminohydride
Lombardo's reagent
Lossen rearrangement
macromolecules
see polymers
malic acid
malonic ester alkylation
manganese dioxide oxidations
Mannich reactions
the Markovnikov rule
mass spectrometry
base peak
EI source
electron & mass parity rules
fragment ions
fragmentation patterns
fragment ion tables
rearrangement mechanisms
high resolution measurements
isotopic masses
mass calculator
mass spectrometer diagram
molecular ion
radical cation
mechanism of reactions
acetal formation
acylation
curved arrow use
enamine formation
ester hydrolysis
free radical halogen substitution
E1 mechanism for elimination
E2 mechanism for elimination
electrophilic addition to alkenes
esterification mechanism
diene additions
rate determining vs. product determining steps
imine formation
(
animation
)
nucleophilic substitution
S
N
1 mechanism
nucleophilic substitution
S
N
2 mechanism
animation
characteristics of S
N
2 mechanism
nucleophilic substitution of halobenzenes
S
N
Ar mechanism
mechanism of ozonolysis
the Wittig reaction
Meerwein-Verley-Ponndorf reduction
melting point
mercaptan
meso compounds
metal exchange reactions
metathesis of alkenes
methanonium ion
methylenetriphenylphosphorane
micelles
Michael reaction
(supplemental material)
microscopic reversibility
Mitsunobu reaction
(supplemental material)
Möbius transition state
molecular compound
molecular dipole moment
molecularity
molecular orbitals
HOMO & LUMO
HOMO & LUMO in spectroscopy
orbital coefficients
molecular orbital model
ethene
molecular orbital model
conjugated dienes
molecular orbital model
conjugated triene
molecular orbital model
benzene
Hückel & Möbius orbitals
correlation diagrams
of fluorine
of nitrogen
of oxygen
determining molecular structure
(supplemental material)(
molecular weight of polymers
monomer
morphine
Mosher's acid
Mukaiyama aldol
multiple bonding
muscarine
muscone
naphthalene
N-bromosuccinimide (NBS)
Nef reaction
neighboring group assistance
niacin
nicotine
ninhydrin
nitration of benzene
nitrogen cycle
nitrous acid reaction with 1º-amines
nitrous acid reaction with aryl-amines
nitroxide radicals
NMO
N-methylmorpholine-N-oxide
noble gases
nonclassical cations
nomenclature
of alcohols
of aldehydes & ketones
of alkanes & related hydrocarbons
of amines
of bicyclic compounds
of carboxylic acids
of carboxylic acid derivatives
of ethers
nomenclature priority of IUPAC suffixes
nonionic reactions
nuclear magnetic resonance spectroscopy
see Spectroscopy
nucleic acids
nucleophile
nucleophilic substitution
nucleophilic substitution mechanisms
nucleophilic substitution of benzene derivatives
nucleophilic substitution of carboxyl derivatives
nucleophilic substitution of pyridine
nucleophilicity
the alpha effect
(supplemental material)
nucleophilicity & basicity
(supplemental material)
nucleoside
nucleotide
Oppenauer oxidation
optical activity
organometallic compounds
carbenoid reagents
Lombardo's reagent
Peterson's reagent
Simmons-Smith reagent
exchange reactions
Gilman reagents
main group metals
Li, Mg, Cd, Zn etc.
organocadmium reagents
reactions with electrophiles
transition metals
alkylidene (carbene) complexes
Fischer & Schrock
properties
reactions
configurations of metal complexes
ligands
reaction classes
carbon-carbon bond formation
osmium tetroxide reaction with alkenes
oxacations
oxaphosphatane
oxidation
alcohol oxidations
catalyzed by oxygen in air
by DMP
Dess-Martin Periodinane
by DMSO
by manganese dioxide
by TEMPO
by TPAP
perruthenate
hydroxylation of alkenes
epoxidation of alkenes
alkyl side-chain oxidation of arenes
Tollens, Benedict & Fehling oxidation of aldehydes
oxidative addition
oxidation states of carbon
oxidation states of nitrogen
oxidation states of phosphorus
oxidation states of sulfur
oxidizing agents
PCC, PDC and others
oxime
oxiranes
oxone
oxy-Cope rearrangement
oxymercuration
ozone & ozonolysis
mechanism of ozonolysis (supplemental material)
palladium catalysis
Paneth's experiment
paracyclophane
parallel kinetic resolution
Pascal's triangle
Pauson-Khand reaction
Payne rearrangement
PCC, PDC and other oxidants
(supplemental material)
p-d double-bonding
penicillin G
peracids
pericyclic reactions
concertedness
cycloaddition
dipolar cycloadditions
electrocyclic
ene reactions
sigmatropic rearrangement
configurational notation
Lewis acid catalysis of cycloadditions
theoretical models
periodic acid & glycol cleavage
periodic table
Perkin, W. H.
permanganate reaction with alkenes
peroxide initiators
perspective formulas
Peterson's reagent
phenanthrene
phenols
acidity of phenols
electrophilic substitution
oxidation of phenols
phenonium ion
phenyl group
phenylhydrazone
phosphorus compounds
nucleophilicity
oxidation states
reducing character of phosphines
ylide formation
ylide reaction
phosphines
phospholipids
phosphorus oxychloride
phosphorus trihalides
e.g. chloride & bromide
limitations in their use
photochemistry
fluorescence
Franck-Condon principle
Jablonski diagram
internal conversion
intersystem crossing
laws of
phosphorescence
quantum yield
singlet & triplet states
reactions
[2+2] cycloaddition
aryl ketone reactions
type I & type II cleavage
cyclohexadienones
the de Mayo reaction
diene and polyene isomerization
the Paterno-Büchi reaction
photoenolization
stilbene isomerization
sensitized isomerization
the Yang reaction
pi bonds
pi complex
pinacols
pinacol rearrangement
piperine
pKa
polar covalent bonds
polar reactions
polar solvents
polarimeter
polymers
addition (chain-growth) polymers
cold-drawing fibers
condensation (step-growth) polymers
copolymers
addition copolymers
block copolymers
crystallinity of polymers
M
n
number average molecular weight
M
w
weight average molecular weight
polymer morphology and properties
regioisomerism of polymers
head-to-tail polymerization
stereoisomerism of polymers
atactic
isotactic
syndiotactic
synthesis of addition polymers
radical chain-growth polymerization
cationic chain-growth polymerization
anionic chain-growth polymerization
Ziegler-Natta catalytic polymerization
T
g
the glass transition
T
m
the melt transition
thermoplastic & thermosetting plastics
vulcanization of rubber
polymorphism
primary carbon
principles of acid-base equilibria
principles of resonance
Prins reaction
prochiral
progesterone
properties of
prostaglandins
prostereogenic
proteins, peptides & amino acids
amino acids
cysteine-cystine interconversion
electrophoresis
essential amino acids
formulas & abbreviations
Henderson-Hasselbach equation
isoelectric point
(pI)
L
-configuration
pKa's of polyfunctional amino acids
reactions of amino acids
esterification
N-acylation
ninhydrin reaction
synthesis of amino acids
amination of alpha-bromo acids
Gabriel synthesis
Strecker synthesis
resolution of racemic amino acids
uncommon amino acids
zwitterion form
conjugated proteins
fibrous proteins
globular proteins
denaturation
peptides & peptide bonds
cyclic peptides
examples of common peptides
primary structure of peptides
C-terminal analysis
cyanogen bromide cleavage
determining the primary structure
Edman degradation
N-terminal analysis
selective peptide cleavage
peptide synthesis
Merrifield synthesis
protective groups
carbobenzoxy
(Cbz)
t-butoxycarbonyl
(BOC)
secondary & tertiary structure
the α-helix
β-pleated sheet
dihedral angles Φ & Ψ
other structures such as turns
angiotensin
collagen
endothelin
lysozyme
thioredoxin
quaternary structure
hemoglobin
mellitin
tropomyosin
structure-property relationships
protic solvents
pseudoasymmetric center
pseudoephedrine
RNA
purine bases
pyrene
pyrethrin
pyridinium chlorochromate
PCC
2-pyridone
pyrimidine bases
pyrolytic syn-eliminations
(supplemental material)
pyruvic acid
quaternary carbon
quinine
quinones
R/S notation
R,S notation examples
in morphine, strychnine & taxol
racemate
racemization
racemic compound
radical initiators
rate-determining step
rate equation
radicals
configuration
radical stability order
formation by bond homolysis
formation by electron transfer
formation by atom abstraction
reactions of radicals
radical chain reactions
radical addition to alkenes I
radical addition reactions II
substitution reactions
elimination reactions
radical cyclizations
recombination reactions
cage effect
radical quenching agents
reaction
(defined)
reaction arrows
reaction classes
reaction characteristics
reaction constants
reaction energetics
reaction mechanism
reaction profiles
reaction rates
& kinetics
re and si enantiotopic faces
reaction summaries for carbonyl compounds
reactive intermediates
rearrangement defined
rearrangement example
rearrangement of carbocations
cationic rearrangements
rearranement in Friedel-Crafts alkylation
anionic rearrangements
benzylic acid
Brook
Favorskii
Grob fragmentation
Payne
Sommelet-Hauser
Stevens
Wittig
rearrangements to cationic sites
Arndt-Eistert
Baeyer-Villiger
Beckmann
Curtius
Hofmann
Lossen
pinacol
Stieglitz
Tiffeneau-Demjanov
Wagner-Meerwein
Wolff
redox states of carbon
reducing agents overview
(supplemental material)
for carboxylic derivatives
(supplemental material)
reducing sugars
reduction
alkene reduction
alkyne reduction
Birch reduction
alpha-substituted ketones
Clemmensen reduction
Meerwein-Verley-Ponndorf reduction
(supplemental material)
metal hydride reduction
reduction of nitro groups & aryl ketones
Wolff-Kishner reduction
reductive amination
regioselectivity
regioselectivity and the Markovnikov rule
regioselectivity of enolate anion formation
regioselectivity in the Diels-Alder reaction
reductive elimination
replication fork
reserpine synthesis
R. B. Woodward
resolution defined
resolution of racemates
Pasteur's resolution of racemic tartaric acid
resolution of 1,1'-binaphthyl
resolution by diastereoisomer separation
resolution of racemic amino acids
resonance
resonance arrow
resonance hybrid
resonance of conjugated dienes
resonance stabilization
resonance stabilization of carboxylate anion
resonance stabilization of radicals
resonance of benzene substituents
resonance substituent effects, modification of
retrosynthetic analysis
rhodopsin photochemistry
ribosomes
ring expansion rearrangement
ring strain in reactivity of cyclopropane
rings + double-bonds rule
RNA
role in protein synthesis
RNA codons
risk analysis
Robinson-Schopf synthesis
rotational barrier analysis
(supplemntal material)
in saturated alkanes
in saturated alkanes
in methanol & methylamine
in 1,2-dihaloethane
in alkenes
in carbonyl compounds
rubber
saccharides
see carbohydrates
salcomine
Sanger's reagent
santonic acid
santonin photochemistry
saturated
Schiff base
Schmidt rearrangement
also see Beckmann rearrangement
Schrock alkylidenes
secondary carbon
semicarbazone
kinetic vs. equilibrium control
s-cis & s-trans conformations of dienes
selectivity factor/A>
sequence rule
serotonin
shorthand formulas
sigma bonds
sigmatropic reactions
[1,2]-shifts
[1,5]-H-shifts
[2,3]-shifts
[3,3]-shifts
silyl ethers
Simmons-Smith reagent
S
N
2 mechanism
(
animation
)
soap & detergents
sodium acetylide
sodium amide
sodium borohydride
sodium triacetoxyborohydride
solvation
of ions
solvent effects in nmr
solvents
protic & aprotic
solvolysis
Sommelet-Hauser rearrangement
specific rotation
Spectroscopy
absorbance
infrared spectroscopy
fingerprint region
force constant
group frequency region
group frequencies
alcohol & phenol absorptions
alkene absorptions
amine absorptions
arene absorptions
carbonyl absorptions
carboxylic acid absorptions
carboxyl derivative absorptions
vibrational states
wavelength & frequency units
mass
see
mass spectrometry
molar absorptivity
nmr spectroscopy
chemical shift
anisotropy effects
carbon shift range
deshielding
hydrogen bonding influence
inductive effect
isochronous nuclei
proton shift range
shielding
solvent effects
TMS reference
CW spectrometer
deuterated solvents
FT spectroscopy
free induction decay
FID
Larmor frequency
nuclear spin
I
relaxation
signal strength
spin-spin coupling
coupling constant
J
general rules concerning
first order patterns
second order perturbation
Karplus equation
Pascal triangle
spin decoupling
problems & resources
transmittance
visible & ultraviolet
electronic spectroscopy
chromophore
conjugated chromophores
electronic excitation
empirical rules for calculating absorption
spectrometer diagram
terminology for absorption shifts
e.g. bathochromic
spin label
(supplemental material)
spiro compounds
stability
chemical & thermodynamic
chemical & thermodynamic
staggered conformer
standard state
thermodynamics
standard state for entropy
starch
see carbohydrates
stereoelectronic effects
in S
N
2 reactions
in E2 reactions
in addition reactions
in carbonyl reactions
Cram model
Karabatsos model
Felkin-Ahn model
in cyclization reactions
Baldwin's rules
in conformational equilibria
in enolization
stereogenic element
chiral center
e.g. asymmetric carbon
in allenes
chiral axis
chiral plane
stereogenic nitrogen
bridged amines & aziridines
stereoisomers
stereoisomer relationship chart
stereospecificity
stereoselectivity
stereoselective addition to double bonds
stereoselectivity of carbonyl addition reactions
steric crowding
steric effects
steric hindrance
in conformational equilibria
of cyclohexyl substituents
in transition state energy
transannular steric strain
steroids
see lipids
Stetter reaction
Stevens rearrangement
Stieglitz rearrangement
Stille coupling
Stork-Eschenmoser hypothesis
Stork enamine synthesis
strain
allylic strain
1,2 & 1,3
angle strain
eclipsing strain
torsional strain
torsional strain
Pitzer strain
structural formulas
substituent constants
substituent effects in reactions of benzene
substituent effects on carboxylic acid acidity
substituted cyclohexane conformers
substitution reaction defined
substitution reaction example
S
N
1 & S
N
2 mechanisms
electrophilic substitution of benzene
electrophilic substitution of 5-membered heterocycles
electrophilic substitution of 6-membered heterocycles
nucleophilic substitution of benzene derivatives
nucleophilic substitution of pyridine
sugars
see carbohydrates
sulfides
(supplemental material)
sulfonate esters
e.g. mesylates and tosylates
sulfonation of benzene
sulfonium salts
sulfur compounds
(supplemental material)
nucleophilicity
oxidation states
ylide formation
ylide reaction
superbases-nonionic
(supplemental material)
suprafacial
& antarafaciaL
surfactant
Suzuki coupling
sweetening agents
high fructose corn syrup
synthetic sweeteners
relative sweetness
FDA approval of
stevia glycosides
Swern oxidation
(supplemental material)
symmetry elements
symmetry point groups
syn-anti addition
syn-anti stereo nomenclature
(supplemental material)
syn-eliminations
synthesis
applications of condensation reactions
carbon-carbon bond formation
cascade reactions
modern criteria
historical background
linear vs. convergent
retrosynthetic analysis
simple examples
synthetic transform
umpolung
tartaric acids
tautomerization defined as a rearrangement
tautomerization example
tautomerism in alkyne hydrations
TEMPO
a nitroxyl radical
terpenes
see lipids
rearrangements of terpenes
tertiary carbon
testosterone
tetrahedral configuration
tetrahydrocannabinol
THC
thermal cracking
thermodynamics
thermodynamic stability
thiols
(supplemental material)
thionyl chloride
characteristics of reactions
Thorpe-Ingold effect
threo-erythro notation
(supplemental material)
tetrose configurations
thiamine
ylide-like conjugate base
thiazolium salts as acyl anion equivalents
Tiffeneau-Demjanov rearrangement
Tollens' oxidation
toxicity
transcription
transition state
aldol reaction
E2 mechanism
S
N
2 mechanism
electrophilic substitution of benzene derivatives
transition metal bonding to alkenes
transition metal complexes
transition metal ligands
translation
triglycerides
see lipids
trigonal configuration
triphenylmethyl radical
triphenylphosphine
triphenylphosphine oxide
tropinone
Truse-Smiles rearrangement
twist conformer
two or more stereogenic centers
ultraviolet-visible spectroscopy
see Spectroscopy
valence electrons
valence octet
valence shell
valence
valence of common elements
van der Waals attraction
vanillin
vicinal
viewing rule
Vilsmeier reagent
vinyl group
vinyl cation
(carbocation stability order)
vinyl compounds
vinylagous systems
acidic hydroxyl compounds
also vinylagous esters and amides
(supplemental material)
β-elimination
conjugate addition
Michael reaction
vinylagous activation of C-H
vitamins A, D, E & K
vitamin C
vitamin D photochemistry
Vollardt trimerization
VSEPR
vulcanization of rubber
Wagner-Meerwein rearrangement
water solubility
wavelength
wedge-shaped bonds
Weiss reaction
Wilkinson's catalyst
the Wittig reaction
[1,2]-Wittig rearrangement
[2,3]-Wittig rearrangement
Wolff-Kishner reduction
Wolff rearrangement
Wöhler, F. (urea synthesis)
Woodward-Fieser rules for calculating UV absorption
xanthate pyrolysis
ylides
reactions of phosphorous ylides
reactions of sulfur ylides
Zaitsev rule
zig-zag configurational formulas (supplemental material)
zinc alkyl reagents
zinc-copper couple
zwitterion form of amino acids