Index for Organic Chemistry On Line

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
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

kinetic acidity

base catalyzed isotope exchange

of nitroalkanes

structural reorganization factor

hybridization

inductive effects

resonance stabilization of carboxylate anion

super acid
activating substituents
activation energy
activation enthalpy

and transition state
acyl anion equivalent
acylation reactions

specialized acylation reagents
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
age of plastics (the)
alcohols

substitution of hydroxyl hydrogen

nucleophilic substitution of OH

by hypervalent phosphorous reagents

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

Zimmerman-Traxler transition state
aldoses see carbohydrates
aliphatic
alkali metals
alkaloids
alkane nomenclature
alkene configurational isomers
alkene/alkyne nomenclature
alkene reactions

addition of Brønsted acids

hypohalous acid additions

radical polymerization

stereoselectivity of addition

hydroboration stereoselectivity
alkyl groups
alkyl halide reactions

reaction variables

nucleophilic substitution

alkyl group influence

S_N1 mechanism solvolysis

solvent effects

steric hindrance (animation)

beta-elimination

anti-stereospecificity

beta-hydrogen requirement

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

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
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
amino acids see proteins
aminolysis
amphiphilic & amphipathic
amphoterism
amylose
anandamide
anchimeric assistance
angle strain
anion solvation
anion stability order
anionic rearrangements
anisotropy
annulenes
anomers see carbohydrates
anomeric effect
antarafacial & suprafaciaL
anthracene
anti conformer
anti-syn stereo nomenclature
anti-syn addition
antiaromaticity
aromatic stabilization
aromaticity
aromaticity principles

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
aufbau principle
axial
azacations
aziridine inversion

the Baldwin rules
barrelene
Barton reaction
base pairing
basicity, Brønsted defined
basicity of amines

of pyridines and related heterocycles
basicity of amides
basic reagents
basicity & nucleophilicity
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
benzilic acid rearrangement
benzoin condensation
benzyl group
benzyl radical
benzyne
beta-elimination
betaine
bicyclic compounds
bilirubin photochemistry
biosynthetic pathways
biotin
biphenyl stereoisomers
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
bond-breaking
bond-making
borane (diborane)
Bredt's rule
bridged ring compounds
bromination
bromonium ion intermediate
Brønsted theory
Brook rearrangement
buckminsterfullerene
bullvalene
Bürgi-Dunitz trajectory
butane conformers

C₆₀
cage effect in radical reactions
caffeine & related compounds
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 effects

carbocation stability order

nonclassical carbocations

carbocation rearrangement

stable carbocations tropylium & trityl
carbodiimides
carbohydrates

aldose

anomers

cellobiose, maltose & sucrose

furanose & pyranose forms

glucose

ketoses

Kiliani-Fischer synthesis

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

deoxygenation (reduction)

Wolff-Kishner

Clemmensen

thioacetal hydrogenolysis

enantioselective reduction

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

stable hydrates & hemiacetals
carbonyldiimidazole
carboxylic acids

acidity

derivatives

nomenclature

physical properties

reactions: acyl substitution, reduction, organometallic reagents,

reactions at the α carbon: Claisen & Dieckmann condensations

substitution of the hydroxyl hydrogen

substitution of the hydroxyl group
β-carotene
carvone
catalyst

acid-base catalysis

catalysis of the aldol reaction

catalytic hydrogenation

Lewis acid catalysis of cycloadditions

structure of Sharpless epoxidation catalyst
cellulose see carbohydrates
central dogma
chain reaction
chain reaction in bromination (animation)
chair conformer
chelation effect in stereoselectivity of carbonyl additions
cheletropic addition of SO₂
chemical reaction (defined)
chemical reaction
chemical stability
Chichibabin reaction
chirality

center

nomenclature of

axial

helical

planar
chiral auxiliary
chloral & chloral hydrate
chlorination
chlorophyll
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

cyclohexane conformations

cyclohexene conformations

s-cis & s-trans conformers of dienes

s-E & s-Z conformers of esters
conglomerate solid
conjugate acid/base pairs
coniine
conjugated dienes
conjugate addition reactions
conrotatory
constitutional isomers
Cope elimination
Cope Rearrangement

degenerate Cope rearrangement
corannulene
Corey-Winter reaction
corn syrup
coronene
cortisone
Couper-Kekulé formula
coupling constants for ¹H 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
denaturation of proteins
derivatives of carboxylic acids

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
directed ortho metalation
disaccharides see carbohydrates
disiamylborane (in hydroboration of alkynes)
disrotatory
dissolving metal reductions

aromatic rings

carbonyl compounds

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
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-alkylation

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
ESR electron spin resonance
Eschenmoser's salt
esterification
ester cleavage
ester pyrolysis
ethane conformers
ethers

nomenclature

preparation Alkoxymercuration & Williamson

reactions

used as protective groups

silyl ethers
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
fluxional molecules
formaldehyde

molecular orbitals

vibrational modes
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

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
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
heme

hemoglobin
hemicellulose
Henderson-Hasselbalch 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
the Hofmann rule
homology
homolysis

thermal

photochemical
homoenolate
homotopic
honey
Horeau's method
hormones
Horner-Wadsworth-Emmons reaction
hula-twist isomerization
Hunsdiecker reaction
Hückel rule
Hünig's base
hybrid orbitals

hybridization states of carbon
hybridization & acidity
hydrazone
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
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

post-translational synthesis
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
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
ladderane compounds
LD₅₀
LDA lithium diisopropylamide
lead tetraacetate & glycol cleavage
Leuckart reaction
levorotatory
Lewis acids
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

acylation

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_N1 mechanism

nucleophilic substitution S_N2 mechanism animation

characteristics of S_N2 mechanism

nucleophilic substitution of halobenzenes S_NAr mechanism

mechanism of ozonolysis

the Wittig reaction
Meerwein-Verley-Ponndorf reduction
melting point
mercaptan
meso compounds
metal exchange reactions
metalation ortho to DMG substituent
metathesis of alkenes
methanonium ion
methylenetriphenylphosphorane
micelles
Michael reaction
microscopic reversibility
Mitsunobu reaction
Möbius transition state
molecular compound
molecular dipole moment
molecularity
molecular orbitals

HOMO & LUMO

HOMO & LUMO in spectroscopy

orbital coefficients

molecular orbital model conjugated dienes

molecular orbital model conjugated triene

molecular orbital model benzene

molecular orbital model formaldehyde

Hückel & Möbius orbitals

correlation diagrams

of fluorine

of nitrogen

of oxygen
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
nisin
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

nucleophilic substitution of carboxyl derivatives

nucleophilic substitution of pyridine
nucleophilicity

the alpha effect
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

palladium catalysis
Paneth's experiment
paracyclophane
parallel kinetic resolution
Pascal's triangle
Pauson-Khand reaction
Payne rearrangement
PCC, PDC and other oxidants
penicillin G
peracids
pericyclic reactions

concertedness

cycloaddition

dipolar cycloadditions

electrocyclic

ene reactions

sigmatropic rearrangement

configurational notation

Lewis acid catalysis of cycloadditions

theorretical 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

laws of

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
pigments
pinacols
pinacol rearrangement
piperine
pKa
plastics-the age of

biodegradable

environmental pollution

recycling & disposal
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
polymethylhydrosilane (PMHS)
polymorphism
polythiophenes
porphyrins
post-translational modification
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

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

insulin

structure-property relationships
protein synthesis by translation

post-translational modification

rna codons

ribosome machinery
protic solvents
pseudoasymmetric center
pseudoephedrine
RNA
purine bases in DNA
purines
pyrene
pyrethrin
pyridinium chlorochromate PCC
2-pyridone
pyrimidine bases
pyrolytic syn-eliminations
pyruvic acid

quaternary carbon
quaternary structure of proteins
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 rates & kinetics
re and si enantiotopic faces
reaction summaries for carbonyl compounds
reactive intermediates
rearrangement defined

rearrangement example

rearrangement of carbocations

rearranement in Friedel-Crafts alkylation
anionic rearrangements

Brook

Payne

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
reducing sugars
reduction

alkene reduction

alkyne reduction

Birch reduction

alpha-substituted ketones

Clemmensen reduction

Meerwein-Verley-Ponndorf reduction

metal hydride reduction

reduction of nitro groups & aryl ketones

reduction by silanes

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 of benzene substituents

resonance stabilization

resonance stabilization of carboxylate anion

resonance stabilization of fused ring aromatic hydrocarbons

resonance stabilization of radicals

resonance in modification of substituent effects,
retrosynthetic analysis
rhodopsin photochemistry
ribosomes
ring expansion rearrangement
ring strain
rings + double-bonds rule
RNA

role in protein synthesis

RNA codons
risk analysis
Robinson-Schopf synthesis
rotational barriers

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
silanes
silyl ethers
Simmons-Smith reagent
S_N2 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

carboxylic acid absorptions

carboxyl derivative absorptions

vibrational states

wavelength & frequency units

mass see mass spectrometry

deshielding

hydrogen bonding influence

shielding

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

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
spiro compounds
stability chemical & thermodynamic

chemical & thermodynamic
staggered conformer
standard state thermodynamics
standard state for entropy
starch see carbohydrates
stereoelectronic effects

in S_N2 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

iin 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
Stryker reagent
substituent constants
substituent effects in reactions of benzene
substituent effects on carboxylic acid acidity
substituted cyclohexane conformers
substitution reaction defined
substitution reaction example

S_N1 & S_N2 mechanisms

electrophilic substitution of benzene

electrophilic substitution of 5-membered heterocycles

electrophilic substitution of 6-membered heterocycles

nucleophilic substitution of benzene

nucleophilic substitution of pyridine
sugars see carbohydrates
sulfides
sulfonate esters e.g. mesylates and tosylates
sulfonation of benzene
sulfonium salts
sulfur compounds

nucleophilicity

oxidation states

ylide formation

ylide reaction
superbases-nonionic
suprafacial & antarafaciaL
sunscreen
surfactant
Suzuki coupling
sweetening agents

high fructose corn syrup

synthetic sweeteners

relative sweetness

FDA approval of

stevia glycosides
Swern oxidation
symmetry elements
symmetry point groups
syn-anti addition
syn-anti stereo nomenclature
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
thionyl chloride

characteristics of reactions
Thorpe-Ingold effect
threo-erythro notation
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_N2 mechanism

electrophilic substitution of benzene derivatives
transition metal bonding to alkenes
transition metal complexes
transition metal ligands
translation
tributyltin hydride
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
unsaturated

valence electrons
valence octet
valence shell
valence
valence of common elements
valence tautomers
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

β-elimination

conjugate addition

Michael reaction

vinylagous activation of C-H
vitamins A, D, E & K
vitamin B complex
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 line formulas
Zimmerman-Traxler transition state
zinc alkyl reagents
zinc-copper couple
zwitterion form of amino acids