Alphabetical Index — Virtual Textbook — OrganicChemistryData.org

Index

A concept index of the textbook, each topic linking to where it is discussed.

Locations are found by semantic match and recomputed when content changes. Sub-topics are indented under their parent.

0–9 · A · B · C · D · E · F · G · H · I · J · K · L · M · N · O · P · Q · R · S · T · U · V · W · X · Y · Z

0–9

[1,2]-Wittig rearrangement 1 · 2 · 3

[2,3]-Wittig rearrangement 1 · 2 · 3

2-pyridone 1 · 2 · 3

A

A-values of cyclohexyl substituents 1 · 2 · 3

abietic acid 1 · 2 · 3

absolute configuration 1 · 2 · 3

acceptor reactant in the aldol reaction 1 · 2 · 3

acetals 1 · 2 · 3

acetoacetic ester alkylation 1 · 2 · 3

achiral diastereomers 1

achirality 1 · 2 · 3

aci-anions from nitroalkanes 1 · 2 · 3

acid-base catalysis (supplemental material) 1 · 2 · 3

acid-base equilibria 1 · 2 · 3

acidic and basic resolving agents 1 · 2 · 3

acidity 1 · 2 · 3

carbon acids 1

α hydrogens 1 · 2 · 3

stereoelectronic factors in enolization 1

carboxylic acids 1 · 2

inductive effects 1 · 2 · 3

resonance effect stabilization of carboxylate anion 1 · 2 · 3

substituent effects advanced treatment 1 · 2 · 3

equilibrium acidity 1 · 2

solvent effects on pKa s 1 · 2 · 3

hybridization 1

kinetic acidity 1 · 2

base catalyzed isotope exchange 1 · 2

of nitroalkanes 1 · 2 · 3

structural reorganization factor 1 · 2 · 3

super acid 1 · 2 · 3

acidity constant Ka 1 · 2 · 3

activating substituents 1 · 2 · 3

activation energy 1 · 2

activation enthalpy 1 · 2

and transition state 1 · 2

acyl anion equivalent 1 · 2 · 3

acyl carbene rearrangements 1

acyl nitrene rearrangements 1

acylation reactions 1 · 2 · 3

specialized acylation reagents (supplemental material) 1 · 2 · 3

acyloin condensation 1 · 2 · 3

acyloins from thiazolium catalyzed aldehyde condensations 1 · 2 · 3

addition reaction defined 1 · 2 · 3

1,2 & 1,4-addition to dienes 1 · 2

addition reaction example 1 · 2 · 3

addition reactions of alkenes 1 · 2 · 3

addition reactions of alkynes 1 · 2 · 3

addition reactions of allenes 1 · 2

addition reactions of benzene 1 · 2

addition to cyclopropane 1 · 2 · 3

alcohols 1 · 2 · 3

nomenclature 1

reactions 1 · 2 · 3

dehydration 1 · 2 · 3

nucleophilic substitution of OH 1 · 2 · 3

by hypervalent phosphorous reagents (supplemental material) 1 · 2 · 3

by way of sulfonate esters 1 · 2 · 3

oxidation 1 · 2 · 3

substitution of hydroxyl hydrogen 1 · 2 · 3

Williamson ether synthesis 1

alcoholysis 1 · 2 · 3

aldehydes & ketones 1 · 2 · 3

addition reactions (irreversible) 1 · 2 · 3

metal hydrides 1 · 2 · 3

organometallic reagents R-Li & R-MgX 1 · 2 · 3

stereoselectivity of addition 1 · 2 · 3

1:3-diastereoselectivity 1 · 2 · 3

chelation effects 1 · 2 · 3

in acyclic compounds 1:2-diastereoselectivity 1 · 2 · 3

polar non-chelation effects 1 · 2 · 3

addition reactions (reversible) 1 · 2

acetal formation 1 · 2

cyanohydrins 1 · 2 · 3

enamine formation 1 · 2 · 3

imine formation (animation) 1 · 2 · 3

water or alcohol 1 · 2 · 3

conjugate addition reactions (supplemental material) 1 · 2 · 3

deoxygenation (reduction) 1 · 2 · 3

Clemmensen 1 · 2 · 3

thioacetal hydrogenolysis 1 · 2 · 3

Wolff-Kishner 1 · 2 · 3

derivatives 1

more derivatives (supplemental material) 1 · 2

enantioselective reduction 1 · 2 · 3

natural compounds 1 · 2

nomenclature 1

oxidation 1 · 2 · 3

preparation 1 · 2

properties 1

reactions at the α-carbon 1 · 2 · 3

the aldol reaction 1 · 2

crossed or mixed aldol reactions 1

dehydration of aldol products 1

electrophilic substitution 1

alkylation 1 · 2 · 3

the ambident character of enolate anions 1

reducing agent summary 1 · 2 · 3

stable hydrates & hemiacetals (supplemental material) 1 · 2 · 3

ylide reactions (supplemental material) 1 · 2

aldehydes see carbonyl compounds 1 · 2 · 3

the aldol reaction 1 · 2

diastereoselectivity 1 · 2

directed aldol reactions 1 · 2 · 3

enamine aldol 1 · 2 · 3

enantioselectivity 1 · 2

enolborinate intermediates 1 · 2

interacting substituent effects 1 · 2 · 3

Mukaiyama aldol 1 · 2 · 3

stereoselective synthesis 1 · 2 · 3

transition state 1 · 2 · 3

aldoses see carbohydrates 1 · 2

aliphatic 1

alkali metals 1 · 2 · 3

alkaloids 1

alkane nomenclature 1

alkene configurational isomers 1 · 2 · 3

alkene reactions 1 · 2 · 3

addition of Brønsted acids 1 · 2

allylic substitution 1

halogen additions 1 · 2 · 3

hydration 1 · 2 · 3

hydroboration 1 · 2

hydrogen addition 1 · 2 · 3

hypohalous acid additions 1 · 2 · 3

Lewis acid additions 1 · 2 · 3

oxidative additions 1 · 2 · 3

oxymercuration 1 · 2 · 3

ozonolysis 1 · 2 · 3

radical additions 1 · 2

radical polymerization 1 · 2

stereoselectivity of addition 1 · 2 · 3

hydroboration stereoselectivity 1 · 2 · 3

alkene/alkyne nomenclature 1 · 2 · 3

alkyl groups 1 · 2 · 3

alkyl halide reactions 1

beta-elimination 1 · 2 · 3

anti-stereospecificity 1 · 2 · 3

beta-hydrogen requirement 1 · 2 · 3

Bredt's rule 1 · 2 · 3

E1 mechanism 1 · 2 · 3

E2 mechanism 1 · 2 · 3

the Zaitsev rule 1 · 2 · 3

formation of organometallic compounds 1 · 2 · 3

nucleophilic substitution 1 · 2 · 3

alkyl group influence 1 · 2 · 3

cation effects (supplemental material) 1 · 2 · 3

molecularity 1 · 2 · 3

nucleophilicity 1

SN1 mechanism solvolysis 1 · 2 · 3

SN2 mechanism 1 · 2 · 3

solvent effects 1 · 2 · 3

steric hindrance (animation) 1 · 2 · 3

reaction variables 1 · 2 · 3

summary comparison of halide reactions 1 · 2 · 3

alkyl lithium reagents 1 · 2

alkylation of stabilized enolate anions 1 · 2

alkyne reactions 1 · 2 · 3

acidity of terminal alkynes 1

addition of nucleophiles 1 · 2 · 3

hydration 1 · 2 · 3

hydroboration 1 · 2

hydrogen addition 1 · 2 · 3

oxidation 1 · 2

preparation from dihalides 1 · 2 · 3

reduction by sodium in ammonia 1 · 2

allenes 1

allotropes of carbon 1 · 2 · 3

allyl group 1

allyl radical 1 · 2 · 3

allylic Grignard addition 1

allylic halogenation 1 · 2 · 3

allylic strain 1,2 & 1,3 1 · 2 · 3

alpha effect (supplemental material) 1 · 2 · 3

ambident anions 1

amide basicity 1 · 2 · 3

amines 1 · 2

amine oxides 1 · 2 · 3

natural compounds 1 · 2 · 3

nitroxide radicals 1 · 2 · 3

nomenclature 1 · 2

preparation of 1º-amines 1

preparation of 2º & 3º-amines 1

primary, secondary & tertiary 1 · 2 · 3

properties 1 · 2

acidity 1

basicity 1

boiling points & solubility 1

reactions 1 · 2

amine oxide elimination 1 · 2 · 3

aryl amines & nitrous acid 1 · 2

Cope elimination 1 · 2 · 3

the Hinsberg test 1 · 2 · 3

Hofmann elimination 1 · 2

reaction with nitrous acid 1

substitution & elimination of nitrogen 1 · 2

substitution at nitrogen 1 · 2

structure-formula relationship extended to N-compounds 1 · 2 · 3

amino acids see proteins 1 · 2 · 3

aminolysis 1 · 2 · 3

amphiphilic & amphipathic 1 · 2 · 3

amphoterism 1 · 2 · 3

amylose 1 · 2 · 3

anandamide 1

anchimeric assistance 1

angle strain 1

anion solvation (supplemntal material) 1 · 2 · 3

anion stability order (supplemental material) 1 · 2 · 3

anionic rearrangements 1

anionic rearrangements 1 · 2

benzylic acid 1 · 2 · 3

Brook 1 · 2

Favorskii 1

Grob fragmentation 1 · 2

Payne 1 · 2

Sommelet-Hauser 1 · 2

Stevens 1

Wittig 1

anisotropy 1

annulenes 1 · 2 · 3

anomeric effect 1

anomers see carbohydrates 1

antarafacial & suprafaciaL 1 · 2

anthracene 1 · 2 · 3

anti conformer 1 · 2 · 3

anti-syn addition 1 · 2 · 3

anti-syn stereo nomenclature (supplemental material) 1 · 2 · 3

antiaromaticity 1

Arndt-Eistert reaction (supplemental material) 1

Arndt-Eistert synthesis 1 · 2 · 3

aromatic stabilization 1 · 2 · 3

aromaticity 1 · 2

aromaticity factors 1 · 2 · 3

aromatic 5-membered heterocycles 1 · 2 · 3

aromatic 6-membered heterocycles 1 · 2 · 3

arrows, use of different kinds 1

aryl diazonium salts 1

coupling reactions 1

substitution reactions 1

asymmetric carbon 1 · 2 · 3

asymmetric induction 1 · 2 · 3

asymmetry 1 · 2 · 3

atomic orbitals 1 · 2 · 3

atomization energy 1 · 2 · 3

atropine 1 · 2 · 3

atropisomers (supplemental material) 1 · 2 · 3

aufbau principle 1

axial 1 · 2 · 3

azacations 1

aziridine inversion 1 · 2 · 3

B

Baeyer-Villiger rearrangement 1 · 2 · 3

the Baldwin rules 1

Barton reaction 1 · 2

base pairing 1 · 2 · 3

basic reagents 1 · 2 · 3

basicity & nucleophilicity (supplemental material) 1 · 2

basicity & solvent effects 1 · 2 · 3

basicity of amides 1 · 2 · 3

basicity of amines 1

of pyridines and related heterocycles 1

basicity, Brønsted defined 1 · 2

basicity, Lewis defined 1 · 2 · 3

Beckmann rearrangement 1 · 2 · 3

Benedict's test 1 · 2

benzene 1 · 2

addition reactions 1 · 2 · 3

electrophilic substitution reactions 1

halogenation, nitration, sulfonation, Friedel-Crafts 1

mechanism of electrophilic substitution (animation) 1

elimination reactions 1 · 2 · 3

nucleophilic substitution reactions 1 · 2 · 3

benzene derivative nomenclature 1

benzene derivatives-substituent effects 1 · 2

Birch reduction 1 · 2 · 3

correlation of reactivity and orientation 1 · 2 · 3

disubstituted benzenes 1 · 2 · 3

halobenzene conversion to organometallic compounds 1 · 2 · 3

hydrolysis of aryl sulfonic acids 1 · 2 · 3

modifying substituent influence 1 · 2 · 3

oxidation of alkyl side-chains 1

reduction of nitro groups & aryl ketones 1 · 2 · 3

substitution orientation 1 · 2

benzene molecular orbitals (animation) 1 · 2 · 3

benzenonium ion 1 · 2 · 3

benzoin condensation 1 · 2 · 3

benzyl group 1 · 2 · 3

benzyl radical 1 · 2 · 3

benzylic acid rearrangement 1 · 2 · 3

benzyne 1

beta-elimination 1 · 2 · 3

betaine 1 · 2 · 3

bicyclic compounds 1 · 2 · 3

bilirubin photochemistry 1 · 2

biosynthetic pathways 1

biotin 1 · 2 · 3

biphenyl stereoisomers (supplemental material) 1 · 2 · 3

Birch reduction 1

boat conformer 1 · 2 · 3

boiling point 1 · 2

bond dipole 1 · 2

bond dipoles and molecular dipole 1 · 2 · 3

bond energy 1

average bond energy 1

bond dissociation energy of C-H 1 · 2 · 3

bond energy and radical stability (supplemental material) 1 · 2 · 3

bond-breaking 1 · 2 · 3

bond-making 1 · 2 · 3

p-d double-bonding 1 · 2 · 3

borane (diborane) 1 · 2

Bredt's rule (supplemental material) 1 · 2

bridged ring compounds 1 · 2 · 3

bromination 1 · 2 · 3

bromonium ion intermediate 1 · 2 · 3

Brook rearrangement 1 · 2 · 3

Brønsted theory 1 · 2

buckminsterfullerene 1 · 2 · 3

butane conformers 1

Bürgi-Dunitz trajectory 1 · 2

C

C.I.P. system 1

C60 1 · 2 · 3

caffeine 1 · 2

cage effect in radical reactions 1

Cahn-Ingold Prelog notation 1 · 2 · 3

examples 1 · 2

in morphine, strychnine & taxol 1 · 2 · 3

camphor 1

Cannizzaro reaction 1 · 2 · 3

canonical structures 1 · 2 · 3

cantharidin 1 · 2 · 3

carbanion 1 · 2 · 3

carbanion stability 1 · 2 · 3

carbene 1 · 2

carbenoid 1 · 2 · 3

carbocation 1 · 2

carbocation rearrangement 1 · 2 · 3

carbocation stability order 1 · 2 · 3

nonclassical carbocations 1

stabilization by inductive, resonance & hyperconjugation effects 1

stable carbocations tropylium & trityl 1 · 2 · 3

carbodiimides 1

carbohydrates 1 · 2

aldaric acid 1 · 2

aldonic acid 1

aldose 1

anomeric effect 1

anomers 1 · 2

cyclodextrins 1

D-configuration 1 · 2

disaccharides 1

cellobiose, maltose & sucrose 1

furanose & pyranose forms 1 · 2

glucose 1 · 2

anomeric forms 1 · 2

cyclic forms 1

structure proof 1 · 2

glycosides 1

α & β-anomers 1 · 2 · 3

glycon & aglycon 1 · 2

Haworth formulas 1

ketoses 1

Kiliani-Fischer synthesis 1 · 2 · 3

osazone formation 1 · 2

oxidation 1 · 2 · 3

polysaccharides 1

cellulose 1

cellulose acetate & nitrate 1 · 2

rayon 1

hemicellulose 1

starch 1

amylopectin 1

amylose 1

Ruff degradation 1 · 2 · 3

tri- & higher oligosaccharides 1 · 2

vitamin C 1

carbon atom classification (1º, 2º, 3º & 4º) 1 · 2 · 3

Carbonyl Compounds 1

carbonyldiimidazole 1 · 2

carboxylic acids 1 · 2

acidity 1 · 2 · 3

inductive effects 1 · 2 · 3

resonance effect stabilization of carboxylate anion 1 · 2 · 3

substituent effects (supplemental material) 1 · 2 · 3

derivatives 1 · 2 · 3

nomenclature 1 · 2 · 3

physical properties 1 · 2

reactions at the α carbon: Claisen & Dieckmann condensations 1 · 2 · 3

reactions: acyl substitution, reduction, organometallic reagents, 1 · 2 · 3

reactivity & IR stretching frequency (supplemental material) 1 · 2 · 3

summary of reducing agents (supplemental material) 1 · 2

fatty acids 1 · 2

natural compounds 1 · 2

nomenclature 1 · 2

physical properties 1

preparation 1

reactions 1 · 2 · 3

decarboxylation 1 · 2

esterification 1

oxidations 1 · 2 · 3

reduction 1 · 2

salt formation 1 · 2 · 3

substitution of the hydroxyl group 1

substitution of the hydroxyl hydrogen 1 · 2 · 3

β-carotene 1 · 2 · 3

carvone 1

catalyst 1 · 2 · 3

acid-base catalysis (supplemental material) 1 · 2

catalysis of the aldol reaction 1 · 2

catalytic hydrogenation 1 · 2

Lewis acid catalysis of cycloadditions 1 · 2 · 3

structure of Sharpless epoxidation catalyst 1 · 2 · 3

cation rearrangements 1

cellulose see carbohydrates 1

central dogma 1

chain reaction 1 · 2 · 3

chain reaction in bromination (animation) 1 · 2 · 3

chair conformer 1 · 2 · 3

chelation effect in stereoselectivity of carbonyl additions 1 · 2 · 3

cheletropic addition of SO2 1 · 2 · 3

chemical reaction (defined) 1

chemical stability 1 · 2

Chichibabin reaction 1 · 2 · 3

chiral auxiliary 1 · 2 · 3

chirality 1 · 2 · 3

axial 1 · 2

center 1 · 2

helical 1 · 2 · 3

nomenclature of 1 · 2 · 3

planar 1 · 2 · 3

chloral & chloral hydrate 1 · 2 · 3

chlorination of alkanes 1

chocolate polymorphs 1

cholesterol 1 · 2 · 3

cholic acid 1 · 2 · 3

chromophore 1 · 2 · 3

chrysene 1

Chugaev reaction 1 · 2 · 3

cis/trans notation 1 · 2 · 3

citral

citric acid 1 · 2 · 3

Claisen condensation 1 · 2

Claisen rearrangement 1 · 2 · 3

Claisen Schmidt reaction 1 · 2 · 3

Clemmensen reduction 1 · 2

cocaine 1

combustion 1

heat of 1

competitive electronic effects inductive & resonance 1 · 2

condensation reactions 1

condensed formulas 1 · 2 · 3

configuration 1

of chiral axes 1 · 2 · 3

of chiral centers 1 · 2

of chiral planes 1 · 2 · 3

configuration inversion of amines 1 · 2 · 3

in aziridines 1 · 2 · 3

configuration of radicals 1 · 2

configurational notation at chiral centers 1 · 2 · 3

lactic acid & carvone 1 · 2

morphine, strychnine & taxol 1

conformational isomers 1 · 2 · 3

biphenyl conformations (supplemental material) 1 · 2 · 3

conformational analysis principles 1 · 2 · 3

conformational enantiomers 1 · 2 · 3

cyclohexane conformations 1 · 2 · 3

cyclohexene conformations 1 · 2 · 3

s-cis & s-trans conformers of dienes 1 · 2

conglomerate solid 1

coniine 1

conjugate acid/base pairs 1 · 2

conjugate addition reactions 1 · 2 · 3

conjugated dienes 1 · 2 · 3

conrotatory 1

constitutional isomers 1 · 2

Cope elimination 1 · 2 · 3

Cope Rearrangement 1 · 2 · 3

corannulene 1 · 2 · 3

Corey-Winter reaction 1 · 2 · 3

corn syrup 1 · 2

coronene 1

cortisone 1 · 2 · 3

Couper-Kekulé formula 1 · 2 · 3

coupling constants for 1H nmr 1 · 2

covalent bonding 1 · 2 · 3

Cram's rule for acyclic diastereoselectivity 1 · 2 · 3

crotyl boron reagents 1 · 2 · 3

enantioselectivity of addition reactions 1 · 2 · 3

crotyl Grignard reagent 1 · 2 · 3

diastereoselectivity of addition reactions 1 · 2 · 3

crown ethers 1 · 2

cumulated dienes 1 · 2

Curtin-Hammett Principle 1

Curtius rearrangement 1 · 2 · 3

curved arrows 1

use in writing mechanisms 1

cyanohydrin 1 · 2 · 3

cyclic halonium ion intermediates 1 · 2 · 3

cyclic mercurium ion intermediates 1 · 2 · 3

cyclic sulfonium ion intermediates 1 · 2 · 3

cyclization vs. dimerization 1 · 2 · 3

cycloaddition 1 · 2 · 3

[2+2] & [4+2] cycloaddition 1 · 2

pericyclic character 1 · 2 · 3

stereospecificity of cycloaddition 1 · 2 · 3

cycloalkanes 1 · 2 · 3

cycloalkane configurational isomers 1 · 2 · 3

cycloalkane conformers 1 · 2 · 3

cycloalkane nomenclature 1

cyclohexane conformations 1 · 2 · 3

discussion 1 · 2 · 3

cyclohexene conformations 1 · 2 · 3

cyclooctatetraene 1

cyclopropanation of alkenes 1 · 2 · 3

cyclopropane addition reactions 1 · 2 · 3

cycloreversion 1 · 2 · 3

D

dashed or hatched bonds 1 · 2 · 3

DBU 1,8-diazabicyclo[5.4.0]undec-7-ene 1 · 2 · 3

deactivating substituents 1 · 2 · 3

dealkylation of esters 1 · 2 · 3

deamination of 1º-amines 1 · 2 · 3

decalin conformations 1 · 2 · 3

decarboxylation of carboxylic acids 1 · 2 · 3

dehydration of 1º-amides to nitriles 1

derivatives of carboxylic acids 1 · 2 · 3

nomenclature 1 · 2 · 3

physical properties 1 · 2

reactions 1 · 2 · 3

acyl substitution 1 · 2 · 3

organometallic reagents 1 · 2

reactions at the α carbon: Claisen & Dieckmann condensations 1 · 2 · 3

reduction 1 · 2 · 3

determining molecular structure (supplemental material)( 1 · 2 · 3

dextrorotatory 1 · 2 · 3

diamond structure 1 · 2 · 3

diastereomeric excess 1 · 2 · 3

diastereomers 1 · 2

diastereoselectivity 1 · 2 · 3

in halogen addition to C=C 1 · 2 · 3

in nucleophile addition to C=O 1 · 2 · 3

diastereoselectivity 1

diastereotopic 1 · 2 · 3

diazo ketone reactions 1

diborane (borane) 1

dicyclohexylcarbodiimide DCC 1 · 2 · 3

Dieckmann condensation 1 · 2 · 3

dielectric constant 1 · 2 · 3

Diels-Alder reaction 1 · 2 · 3

[4+2] cycloaddition 1 · 2

endo effect 1 · 2 · 3

entropy & free energy change 1 · 2 · 3

[regioselectivity 1 · 2 · 3

suprafacial character 1 · 2 · 3

dienes isolated, conjugated & cumulated 1 · 2 · 3

addition reactions of dienes 1

conjugated dienes molecular orbital model (animation) 1 · 2 · 3

Diels-Alder reactions of dienes 1 · 2 · 3

endo & exo stereospecificity 1 · 2 · 3

suprafacial stereospecificity 1 · 2 · 3

diene stability heats of hydrogenation 1 · 2 · 3

s-cis & s-trans conformations 1

dienophile 1 · 2

diethyl malonate or malonic ester 1

dihalide reactions 1 · 2 · 3

dihedral angle 1 · 2 · 3

diimide 1

diisobutylaluminumhydride DIBAH 1 · 2 · 3

dimethyl sulfoxide oxidation of alcohols 1 · 2

dimethylsulfonium methylide 1 · 2 · 3

dimsyl sodium 1 · 2 · 3

dinitrophenylhydrazone DNP derivatives 1

dipolar cycloadditions 1 · 2 · 3

dipole 1 · 2

disaccharides see carbohydrates 1 · 2

disiamylborane (in hydroboration of alkynes) 1

disrotatory 1 · 2

dissolving metal reductions 1 · 2 · 3

aromatic rings 1 · 2 · 3

carbonyl compounds (supplemental material) 1 · 2 · 3

conjugated π-electron systems 1 · 2 · 3

dissymmetry 1 · 2 · 3

DMAP 4-dimethylaminopyridine 1 · 2 · 3

an acyl transfer agent 1 · 2 · 3

DNA 1

replication of 1

secondary structure of 1

donor reactant in the aldol reaction 1 · 2 · 3

double helix 1

dye pigments: natural 1 · 2 · 3

dye pigments: synthetic 1 · 2 · 3

dynamic kinetic resolution 1

Dötz reaction 1 · 2 · 3

E

E/Z notation 1 · 2 · 3

eclipsed conformer 1 · 2

eclipsing strain also see torsional strain 1 · 2

electrocyclic reactions 1 · 2 · 3

electronegativity 1 · 2 · 3

electronic excited state 1 · 2 · 3

electrophile 1 · 2

electrophilic substitution of benzene 1 · 2 · 3

of 5-membered heterocycles 1 · 2 · 3

of 6-membered heterocycles 1 · 2 · 3

electrophoresis 1 · 2 · 3

elimination reaction example 1 · 2 · 3

elimination reactions 1 · 2 · 3

E2 elimination 1

pyrolytic syn-eliminations 1 · 2 · 3

enamide bases 1 · 2 · 3

enamines 1 · 2

enantiomeric excess 1 · 2 · 3

enantiomers 1 · 2 · 3

enantiomorphism 1

enantioselectivity 1 · 2 · 3

enantiotopic atoms or groups 1 · 2 · 3

enantiotopic faces 1 · 2 · 3

endergonic 1 · 2 · 3

endo / exo terminology 1 · 2 · 3

endothermic 1 · 2 · 3

ene reactions 1 · 2

elimination reactions 1 · 2 · 3

intramolecular reactions 1 · 2 · 3

energetics of reactions 1 · 2 · 3

energy 1

enthalpy 1

free energy 1

kinetic & potential 1 · 2 · 3

energy of activation 1

enol tautomer 1 · 2 · 3

electrophilic substitution of 1 · 2 · 3

solvent dependence in dicarbonyl compounds 1 · 2 · 3

enolate anion 1 · 2

the ambident character of enolate anions 1

concentrations in water solution 1 · 2 · 3

configuration (E & Z) 1 · 2 · 3

aldol diastereospecificity of 1 · 2 · 3

stereoselective formation 1 · 2 · 3

β-dicarbonyl compounds 1 · 2 · 3

O vs. C-reaction 1 · 2 · 3

regioselectivity of enolate anion formation 1 · 2

surrogates for enolate anions 1 · 2 · 3

enamines 1

imine conjugate bases enamide bases 1 · 2 · 3

silyl enol ethers 1 · 2

enthalpy 1

entropy 1

ephedrine 1

epimer 1

epoxide reactions 1 · 2 · 3

intramolecular epoxide opening 1 · 2 · 3

epoxides & epoxidation 1 · 2 · 3

Sharpless enantioselective epoxidation 1 · 2 · 3

stereoselectivity of epoxidation 1 · 2 · 3

EPR electron paramagnetic resonance 1

equatorial 1 · 2

equilibrium arrow 1

equilibrium-free energy relationship 1

erythro-threo notation (supplemental material) 1 · 2 · 3

Eschenmoser's salt 1

ESR electron spin resonance 1

ester cleavage (supplemental material) 1 · 2 · 3

ester pyrolysis 1 · 2 · 3

esterification 1

ethane conformers 1 · 2

ethers 1

nomenclature 1

preparation Alkoxymercuration & Williamson 1

reactions 1

silyl ethers (supplemental material) 1 · 2 · 3

used as protective groups (supplemental material) 1 · 2

ethyl acetoacetate or acetoacetic ester 1 · 2 · 3

ethylogy & ethylagous reactions 1 · 2 · 3

eutectic point 1 · 2

exergonic 1 · 2

exo / endo terminology 1 · 2 · 3

exothermic 1 · 2 · 3

F

fats & oils see lipids 1

fatty acids 1 · 2

oleic and stearic acid 1 · 2

unusual fatty acids acid 1 · 2

Favorskii rearrangement 1

Fehling's test 1 · 2

Felkin-Ahn rule for acyclic diastereoselectivity 1 · 2 · 3

ferrocene 1 · 2 · 3

Fischer carbenes 1

Fischer esterification 1 · 2

Fischer indole synthesis 1 · 2 · 3

Fischer projection formula 1

fluorocarbon reactivity 1 · 2 · 3

formal charge 1

formula analysis 1 · 2 · 3

free energy Gibb's free energy 1

free energy of activation 1

free radical bromination (animation) 1 · 2 · 3

free radical reactions 1 · 2 · 3

Fremy's salt 1 · 2

frequency 1

Friedel-Crafts alkylation & acylation 1 · 2 · 3

fullerenes 1 · 2 · 3

functional groups defined 1 · 2

functional group nomenclature (supplemental information) 1 · 2 · 3

functional group reactivity 1 · 2

fused benzene ring compounds 1 · 2

fused ring compounds 1 · 2 · 3

G

galvinoxyl 1 · 2

gauche conformer 1 · 2 · 3

geminal 1 · 2

Gilman reagents 1 · 2 · 3

reaction with acyl chlorides 1 · 2 · 3

glucose see carbohydrates< 1

glycans 1 · 2

glycol cleavage 1 · 2 · 3

glycols 1 · 2 · 3

glycosides see carbohydrates 1 · 2

Gomberg, Moses 1

graphite structure 1 · 2 · 3

Grignard reagents 1 · 2 · 3

Grob fragmentation 1

Grubbs metathesis catalysts 1 · 2

guanidine 1 · 2 · 3

gutta-percha 1

H

haloform reaction 1 · 2 · 3

halogenation of alkanes 1

halogenation of benzene 1 · 2

halogens 1 · 2 · 3

the Hammett equation 1

Hammett rho constants 1

Hammett sigma constants 1

the Hammond postulate 1 · 2 · 3

Hantzsch-Widman nomenclature 1

hatched bonds 1 · 2 · 3

heat of combustion 1

heat of formation 1 · 2 · 3

heat of hydrogenation (alkenes) 1 · 2

heat of hydrogenation (benzene) 1 · 2 · 3

Heck reaction 1 · 2 · 3

helminthosporal

hemicellulose 1

Henderson-Hasselbach equation 1 · 2 · 3

heterocyclic compounds 1

five-membered rings 1 · 2 · 3

four-membered rings 1 · 2 · 3

nomenclature 1

nomenclature examples 1 · 2 · 3

six-membered rings 1 · 2 · 3

three-membered rings 1

heterolysis 1 · 2 · 3

heterotopic 1 · 2 · 3

hexahelicene 1

hexamethylenetetramine 1 · 2 · 3

Hinsberg test 1 · 2

Hofmann elimination 1 · 2 · 3

Hofmann rearrangement 1 · 2 · 3

1º-amine preparation (supplemental material) 1 · 2 · 3

the Hofmann rule 1 · 2

homoenolate 1 · 2 · 3

homology 1 · 2 · 3

homolysis 1 · 2

photochemical 1

thermal 1

homotopic 1 · 2 · 3

honey 1

Horeau's method

Horner-Wadsworth-Emmons reaction 1 · 2 · 3

hula-twist isomerization 1 · 2 · 3

Hunsdiecker reaction 1 · 2 · 3

hybrid orbitals 1 · 2

hybridization states of carbon 1 · 2

hybridization & acidity 1

hydrazone 1

hydride transfer reduction (supplemental material) 1 · 2 · 3

hydroboration 1 · 2

stereoselectivity of 1 · 2 · 3

hydrogen bonding 1 · 2

hydrogen bond acceptor 1 · 2 · 3

hydrogen bond donor 1 · 2

hydrogenation 1

hydrogenation of alkenes 1

hydrogenation of alkynes 1 · 2

hydrogenation of benzene 1 · 2 · 3

hydrolysis 1 · 2 · 3

hydrophilic 1 · 2 · 3

hydrophobic 1 · 2 · 3

hydroxyl group substitution by hypervalent phosphorous reagents 1

hydroxylation 1 · 2 · 3

hyperconjugation 1

hypervalency 1

hypohalous acids 1 · 2

Hückel rule 1

Hünig's base 1

I

imine formation (animation) 1 · 2 · 3

indole, reactions of 1 · 2 · 3

inductive effect and acidity 1

inductive effect defined 1

inductive effect of benzene substituents 1 · 2

inert gases 1 · 2 · 3

infrared spectroscopy see Spectroscopy 1 · 2 · 3

insulin in model display 1

intermolecular forces 1

intramolecular reactions 1 · 2 · 3

compared with intermolecular reactions 1 · 2 · 3

inversion of configuration in amines 1 · 2 · 3

in aziridines 1 · 2 · 3

invert sugar 1

iodoform test 1

iodolactone formation 1 · 2 · 3

ion solvation of ions 1 · 2 · 3

ionic bonding 1

ionic reactions 1 · 2

ionization potential (of alkenes & alkynes) 1 · 2 · 3

isoelectric point (pI) 1

isomer relationship chart 1 · 2 · 3

isomers 1

different properties of 1 · 2 · 3

evidence for structural formulas 1 · 2 · 3

I (continued)

isomers of disubstituted cyclohexanes 1 · 2 · 3

J

Jones reagent 1 · 2 · 3

K

Karabatsos rule for acyclic diastereoselectivity 1 · 2 · 3

kekulene 1 · 2

Kekulé-Couper formula 1 · 2 · 3

ketene 1

keto tautomer 1

ketones see carbonyl compounds 1 · 2 · 3

ketyls 1 · 2 · 3

kinetic acidity 1 · 2

kinetic energy distribution 1 · 2 · 3

kinetic order 1 · 2

kinetic resolution 1

kinetic resolution of racemic amino acids 1

kinetic vs. equilibrium control 1

diene additions 1

enolate anion formation 1

semicarbazone formation (supplemental material) 1

kinetics and reaction rate 1 · 2 · 3

Kolbe-Schmidt reaction 1

L

lactam 1 · 2 · 3

lactic acid 1 · 2

lactone 1 · 2 · 3

alpha-lactone 1 · 2 · 3

beta-lactone 1 · 2 · 3

lactonization 1 · 2 · 3

iodolactonization 1 · 2 · 3

of unsaturated acids 1 · 2 · 3

LD50

LDA lithium diisopropylamide 1 · 2 · 3

lead tetraacetate & glycol cleavage 1 · 2 · 3

Leuckart reaction (supplemental material) 1 · 2 · 3

levorotatory 1 · 2 · 3

Lewis acids (and bases) 1

Lewis formula 1 · 2 · 3

Lindlar's catalyst (for selective reduction of alkynes) 1 · 2 · 3

linear configuration 1 · 2 · 3

linear free energy relationships 1 · 2 · 3

lipids 1 · 2

biosynthesis 1

fats & oils 1

fatty acids arachidonic, lauric, linoleic, oleic, palmitic, stearic 1 · 2

unusual fatty acids 1 · 2

lipidic vitamins A, D, E, K 1

phospholipids 1

liposome 1

planar bilayer 1

prostaglandins & other eicosanoids 1

soaps & detergents 1

amphipathic or amphiphilic 1

micelles 1

surfactant 1

steroids 1

cholesterol & cholic acid 1 · 2

conformations of decalin 1 · 2

terpenes 1

isoprene rule 1

mevalonate & dxp paths 1

polyisoprenoids 1

rubber & gutta-percha 1 · 2 · 3

triglycerides 1

waxes 1

lithium aluminum hydride LAH 1 · 2 · 3

lithium diisopropylamide LDA 1 · 2 · 3

lithium tri-tert-butoxyaluminohydride 1 · 2 · 3

Lombardo's reagent 1 · 2 · 3

Lossen rearrangement 1 · 2 · 3

M

macromolecules see polymers 1

malic acid 1 · 2 · 3

malonic ester alkylation 1 · 2 · 3

manganese dioxide oxidations 1 · 2

Mannich reactions 1

the Markovnikov rule 1 · 2 · 3

mass spectrometry 1 · 2 · 3

base peak 1 · 2 · 3

EI source 1 · 2 · 3

electron & mass parity rules 1 · 2 · 3

fragment ions 1 · 2 · 3

fragment ion tables 1 · 2 · 3

fragmentation patterns 1 · 2 · 3

rearrangement mechanisms 1 · 2 · 3

high resolution measurements 1 · 2 · 3

isotopic masses 1

mass calculator 1

mass spectrometer diagram 1 · 2 · 3

molecular ion 1

radical cation 1 · 2 · 3

mechanism of reactions 1 · 2 · 3

acetal formation 1 · 2 · 3

acylation 1 · 2 · 3

curved arrow use 1

diene additions rate determining vs. product determining steps 1 · 2 · 3

E1 mechanism for elimination 1 · 2

E2 mechanism for elimination 1 · 2 · 3

electrophilic addition to alkenes 1 · 2 · 3

enamine formation 1 · 2 · 3

ester hydrolysis 1 · 2 · 3

esterification mechanism 1 · 2 · 3

free radical halogen substitution 1 · 2 · 3

imine formation (animation) 1 · 2 · 3

mechanism of ozonolysis 1 · 2

nucleophilic substitution of halobenzenes SNAr mechanism 1 · 2 · 3

nucleophilic substitution SN1 mechanism 1 · 2 · 3

nucleophilic substitution SN2 mechanism animation 1 · 2 · 3

characteristics of SN2 mechanism 1 · 2 · 3

the Wittig reaction 1 · 2

Meerwein-Verley-Ponndorf reduction 1 · 2 · 3

melting point 1 · 2

mercaptan 1 · 2 · 3

meso compounds 1

metal exchange reactions 1

metathesis of alkenes 1 · 2 · 3

methanonium ion 1 · 2 · 3

methylenetriphenylphosphorane 1 · 2 · 3

micelles 1

Michael reaction (supplemental material) 1

microscopic reversibility 1 · 2 · 3

Mitsunobu reaction (supplemental material) 1

molecular compound 1 · 2 · 3

molecular dipole moment 1 · 2 · 3

molecular orbitals 1 · 2 · 3

correlation diagrams 1 · 2 · 3

of fluorine 1 · 2 · 3

of nitrogen 1 · 2 · 3

of oxygen 1 · 2 · 3

HOMO & LUMO 1 · 2 · 3

HOMO & LUMO in spectroscopy 1

Hückel & Möbius orbitals 1 · 2

molecular orbital model benzene 1 · 2 · 3

molecular orbital model conjugated dienes 1 · 2 · 3

molecular orbital model conjugated triene 1 · 2 · 3

molecular orbital model ethene 1

orbital coefficients 1 · 2 · 3

molecular weight of polymers 1 · 2

molecularity 1

monomer 1 · 2 · 3

morphine 1 · 2 · 3

Mosher's acid 1 · 2 · 3

Mukaiyama aldol 1 · 2

multiple bonding 1 · 2 · 3

muscarine 1

muscone

Möbius transition state 1 · 2 · 3

N

N-bromosuccinimide (NBS) 1

naphthalene 1 · 2

Nef reaction 1 · 2 · 3

neighboring group assistance 1

niacin 1 · 2 · 3

nicotine 1 · 2 · 3

ninhydrin 1

nitration of benzene 1 · 2 · 3

nitrogen cycle 1 · 2 · 3

nitrous acid reaction with 1º-amines 1

nitrous acid reaction with aryl-amines 1

nitroxide radicals 1 · 2 · 3

NMO N-methylmorpholine-N-oxide 1 · 2 · 3

noble gases 1 · 2 · 3

nomenclature 1 · 2 · 3

of alcohols 1

of aldehydes & ketones 1 · 2

of alkanes & related hydrocarbons 1 · 2

of amines 1

of bicyclic compounds 1 · 2 · 3

of carboxylic acid derivatives 1 · 2 · 3

of carboxylic acids 1

of ethers 1

nomenclature priority of IUPAC suffixes 1 · 2 · 3

nonclassical cations 1 · 2 · 3

nonionic reactions 1 · 2 · 3

nuclear magnetic resonance spectroscopy see Spectroscopy 1 · 2 · 3

nucleic acids 1

nucleophile 1 · 2 · 3

nucleophilic substitution 1 · 2 · 3

nucleophilic substitution mechanisms 1 · 2 · 3

nucleophilic substitution of benzene derivatives 1

nucleophilic substitution of carboxyl derivatives 1 · 2 · 3

nucleophilic substitution of pyridine 1 · 2 · 3

nucleophilicity 1 · 2

the alpha effect (supplemental material) 1 · 2 · 3

nucleophilicity & basicity (supplemental material) 1 · 2

nucleoside 1 · 2 · 3

nucleotide 1

O

Oppenauer oxidation 1 · 2 · 3

optical activity 1

organometallic compounds 1

carbenoid reagents 1 · 2 · 3

Lombardo's reagent 1 · 2 · 3

Peterson's reagent 1 · 2 · 3

Simmons-Smith reagent 1 · 2 · 3

exchange reactions 1

Gilman reagents 1 · 2 · 3

main group metals Li, Mg, Cd, Zn etc. 1 · 2

organocadmium reagents 1 · 2

reactions with electrophiles 1 · 2 · 3

transition metals 1

alkylidene (carbene) complexes Fischer & Schrock 1

properties 1

reactions 1

configurations of metal complexes 1

ligands 1

reaction classes 1

carbon-carbon bond formation 1 · 2

osmium tetroxide reaction with alkenes 1 · 2 · 3

oxacations 1 · 2 · 3

oxaphosphatane 1 · 2 · 3

oxidation 1 · 2 · 3

alcohol oxidations 1 · 2 · 3

by DMP Dess-Martin Periodinane 1

by DMSO 1 · 2

by manganese dioxide 1

by TEMPO 1 · 2 · 3

by TPAP perruthenate 1 · 2 · 3

catalyzed by oxygen in air 1 · 2 · 3

alkyl side-chain oxidation of arenes 1

epoxidation of alkenes 1 · 2 · 3

hydroxylation of alkenes 1 · 2 · 3

Tollens, Benedict & Fehling oxidation of aldehydes 1 · 2 · 3

oxidation states of carbon 1 · 2 · 3

oxidation states of nitrogen 1

oxidation states of phosphorus 1

oxidation states of sulfur 1

oxidative addition 1 · 2 · 3

oxidizing agents 1 · 2 · 3

PCC, PDC and others 1 · 2 · 3

oxime 1 · 2 · 3

oxiranes 1

oxone 1 · 2 · 3

oxy-Cope rearrangement 1 · 2 · 3

oxymercuration 1 · 2 · 3

ozone & ozonolysis 1 · 2 · 3

mechanism of ozonolysis (supplemental material) 1 · 2 · 3

P

p-d double-bonding 1 · 2 · 3

palladium catalysis 1 · 2 · 3

Paneth's experiment 1 · 2 · 3

paracyclophane 1 · 2 · 3

parallel kinetic resolution 1

Pascal's triangle 1

Pauson-Khand reaction 1 · 2 · 3

Payne rearrangement 1

PCC, PDC and other oxidants (supplemental material) 1 · 2 · 3

penicillin G 1 · 2

peracids 1 · 2 · 3

pericyclic reactions 1

concertedness 1 · 2

configurational notation 1 · 2

cycloaddition 1 · 2 · 3

dipolar cycloadditions 1 · 2 · 3

electrocyclic 1 · 2 · 3

ene reactions 1 · 2

Lewis acid catalysis of cycloadditions 1 · 2

sigmatropic rearrangement 1

theoretical models 1 · 2 · 3

periodic acid & glycol cleavage 1 · 2 · 3

periodic table 1 · 2

Perkin, W. H. 1

permanganate reaction with alkenes 1 · 2 · 3

peroxide initiators 1 · 2 · 3

perspective formulas 1 · 2 · 3

Peterson's reagent 1 · 2 · 3

phenanthrene 1 · 2 · 3

phenols 1

acidity of phenols 1

electrophilic substitution 1 · 2

oxidation of phenols 1

phenonium ion 1 · 2 · 3

phenyl group 1 · 2 · 3

phenylhydrazone 1

phosphines 1 · 2

phospholipids 1

phosphorus compounds 1

nucleophilicity 1

oxidation states 1

reducing character of phosphines 1

ylide formation 1

ylide reaction 1

phosphorus oxychloride 1 · 2 · 3

phosphorus trihalides e.g. chloride & bromide 1 · 2 · 3

limitations in their use 1 · 2 · 3

photochemistry 1 · 2

fluorescence 1 · 2

Franck-Condon principle 1 · 2 · 3

internal conversion 1 · 2

intersystem crossing 1 · 2

Jablonski diagram 1 · 2 · 3

laws of 1

phosphorescence 1

quantum yield 1

reactions 1 · 2 · 3

[2+2] cycloaddition 1 · 2 · 3

aryl ketone reactions 1 · 2 · 3

type I & type II cleavage 1 · 2 · 3

cyclohexadienones 1

the de Mayo reaction 1 · 2

diene and polyene isomerization 1 · 2 · 3

the Paterno-Büchi reaction 1

photoenolization 1

stilbene isomerization 1

sensitized isomerization 1

the Yang reaction 1 · 2 · 3

singlet & triplet states 1 · 2 · 3

pi bonds 1 · 2 · 3

pi complex 1

pinacol rearrangement 1

pinacols 1 · 2

piperine 1

pKa 1 · 2

polar covalent bonds 1 · 2 · 3

polar reactions 1 · 2 · 3

polar solvents 1 · 2 · 3

polarimeter 1

polymers 1

addition (chain-growth) polymers 1

cold-drawing fibers 1

condensation (step-growth) polymers 1

copolymers 1

addition copolymers 1

block copolymers 1

crystallinity of polymers 1 · 2

Mn number average molecular weight 1 · 2

Mw weight average molecular weight 1

polymer morphology and properties 1

regioisomerism of polymers 1 · 2 · 3

head-to-tail polymerization 1 · 2 · 3

stereoisomerism of polymers 1 · 2 · 3

atactic 1 · 2 · 3

isotactic 1 · 2 · 3

syndiotactic 1 · 2 · 3

synthesis of addition polymers 1

anionic chain-growth polymerization 1

cationic chain-growth polymerization 1

radical chain-growth polymerization 1

Ziegler-Natta catalytic polymerization 1

Tg the glass transition 1

thermoplastic & thermosetting plastics 1

Tm the melt transition 1 · 2 · 3

vulcanization of rubber 1

polymorphism 1

primary carbon 1 · 2 · 3

principles of acid-base equilibria 1 · 2 · 3

principles of resonance 1 · 2 · 3

Prins reaction 1 · 2 · 3

prochiral 1 · 2 · 3

progesterone 1

properties of 1

prostaglandins 1

prostereogenic 1

proteins, peptides & amino acids 1 · 2

amino acids 1

cysteine-cystine interconversion 1

electrophoresis 1 · 2 · 3

essential amino acids 1

formulas & abbreviations 1 · 2 · 3

Henderson-Hasselbach equation 1 · 2 · 3

isoelectric point (pI) 1

L-configuration 1

pKa's of polyfunctional amino acids 1 · 2 · 3

reactions of amino acids 1 · 2 · 3

esterification 1

N-acylation 1 · 2 · 3

ninhydrin reaction 1

synthesis of amino acids 1

amination of alpha-bromo acids 1 · 2

Gabriel synthesis 1

resolution of racemic amino acids 1 · 2 · 3

Strecker synthesis 1

uncommon amino acids 1 · 2

zwitterion form 1 · 2

conjugated proteins 1

denaturation 1

fibrous proteins 1

globular proteins 1 · 2 · 3

peptide synthesis 1

Merrifield synthesis 1

protective groups 1 · 2 · 3

carbobenzoxy (Cbz) 1 · 2 · 3

t-butoxycarbonyl (BOC) 1 · 2 · 3

peptides & peptide bonds 1

cyclic peptides 1

examples of common peptides 1 · 2 · 3

primary structure of peptides 1

C-terminal analysis 1

cyanogen bromide cleavage 1

determining the primary structure 1 · 2 · 3

Edman degradation 1

N-terminal analysis 1

selective peptide cleavage 1

quaternary structure 1

hemoglobin 1

melittin 1

tropomyosin 1

secondary & tertiary structure 1

angiotensin 1 · 2 · 3

collagen 1 · 2

dihedral angles Φ & Ψ 1

endothelin 1 · 2

lysozyme 1 · 2

other structures such as turns 1

β-pleated sheet 1

thioredoxin 1

the α-helix 1

structure-property relationships 1 · 2 · 3

protic solvents 1 · 2 · 3

pseudoasymmetric center 1 · 2 · 3

pseudoephedrine 1

purine bases 1 · 2 · 3

pyrene 1 · 2 · 3

pyrethrin 1

pyridinium chlorochromate PCC 1 · 2 · 3

pyrimidine bases 1 · 2 · 3

pyrolytic syn-eliminations (supplemental material) 1 · 2 · 3

pyruvic acid 1 · 2 · 3

Q

quaternary carbon 1 · 2 · 3

quinine 1 · 2 · 3

quinones 1 · 2 · 3

R

R/S notation 1 · 2 · 3

in morphine, strychnine & taxol 1 · 2 · 3

R,S notation examples 1 · 2 · 3

racemate 1

racemic compound 1 · 2 · 3

racemization 1 · 2 · 3

radical initiators 1 · 2 · 3

radicals 1 · 2

cage effect 1

configuration 1

elimination reactions 1 · 2 · 3

formation by atom abstraction 1 · 2 · 3

formation by bond homolysis 1

formation by electron transfer 1 · 2 · 3

radical addition reactions II 1 · 2

radical addition to alkenes I 1 · 2

radical chain reactions 1 · 2 · 3

radical cyclizations 1 · 2

radical quenching agents 1

radical stability order 1 · 2

reactions of radicals 1 · 2 · 3

recombination reactions 1 · 2 · 3

substitution reactions 1 · 2 · 3

rate equation 1 · 2 · 3

rate-determining step 1

re and si enantiotopic faces 1 · 2 · 3

reaction (defined) 1 · 2 · 3

reaction arrows 1

reaction characteristics 1

reaction classes 1

reaction constants 1 · 2 · 3

reaction energetics 1

reaction mechanism 1

reaction profiles 1 · 2 · 3

reaction rates & kinetics 1 · 2 · 3

reaction summaries for carbonyl compounds 1 · 2 · 3

reactive intermediates 1

rearrangement defined 1 · 2 · 3

cationic rearrangements 1

rearranement in Friedel-Crafts alkylation 1 · 2 · 3

rearrangement example 1 · 2 · 3

rearrangement of carbocations 1 · 2 · 3

rearrangements to cationic sites 1 · 2 · 3

Arndt-Eistert 1 · 2

Baeyer-Villiger 1 · 2 · 3

Beckmann 1 · 2

Curtius 1 · 2

Hofmann 1 · 2

Lossen 1 · 2 · 3

pinacol 1

Stieglitz 1 · 2

Tiffeneau-Demjanov 1 · 2

Wagner-Meerwein 1 · 2 · 3

Wolff 1 · 2 · 3

redox states of carbon 1 · 2 · 3

reducing agents overview (supplemental material) 1 · 2

for carboxylic derivatives (supplemental material) 1 · 2

reducing sugars 1

reduction 1 · 2 · 3

alkene reduction 1 · 2 · 3

alkyne reduction 1 · 2 · 3

alpha-substituted ketones 1 · 2 · 3

Birch reduction 1

Clemmensen reduction 1 · 2 · 3

Meerwein-Verley-Ponndorf reduction (supplemental material) 1 · 2 · 3

metal hydride reduction 1 · 2 · 3

reduction of nitro groups & aryl ketones 1

Wolff-Kishner reduction 1 · 2 · 3

reductive amination 1 · 2 · 3

reductive elimination 1

regioselectivity 1

regioselectivity and the Markovnikov rule 1 · 2 · 3

regioselectivity in the Diels-Alder reaction 1 · 2 · 3

regioselectivity of enolate anion formation 1

replication fork 1 · 2 · 3

reserpine synthesis R. B. Woodward 1 · 2 · 3

resolution defined 1

resolution of racemates 1

Pasteur's resolution of racemic tartaric acid 1 · 2

resolution by diastereoisomer separation 1 · 2

resolution of 1,1'-binaphthyl 1 · 2

resolution of racemic amino acids 1 · 2 · 3

resonance 1 · 2

resonance arrow 1

resonance hybrid 1

resonance of benzene substituents 1 · 2 · 3

resonance of conjugated dienes 1 · 2 · 3

resonance stabilization 1

resonance stabilization of carboxylate anion 1 · 2

resonance stabilization of radicals 1 · 2 · 3

resonance substituent effects, modification of 1 · 2 · 3

retrosynthetic analysis 1 · 2 · 3

rhodopsin photochemistry 1

ribosomes 1

ring expansion rearrangement 1 · 2 · 3

ring strain in reactivity of cyclopropane 1

rings + double-bonds rule 1 · 2 · 3

risk analysis 1

RNA 1

RNA codons 1

role in protein synthesis 1

Robinson-Schopf synthesis 1 · 2 · 3

rotational barrier analysis (supplemntal material) 1 · 2 · 3

in 1,2-dihaloethane 1 · 2 · 3

in alkenes 1 · 2 · 3

in carbonyl compounds 1 · 2 · 3

in methanol & methylamine 1 · 2 · 3

in saturated alkanes 1 · 2 · 3

rubber 1

S

s-cis & s-trans conformations of dienes 1 · 2

saccharides see carbohydrates 1 · 2

salcomine 1 · 2 · 3

Sanger's reagent 1 · 2 · 3

santonic acid 1

santonin photochemistry 1

saturated 1 · 2 · 3

Schiff base 1 · 2 · 3

Schmidt rearrangement also see Beckmann rearrangement 1 · 2 · 3

Schrock alkylidenes 1

secondary carbon 1 · 2 · 3

selectivity factor/A> 1 · 2 · 3

semicarbazone 1

kinetic vs. equilibrium control 1

sequence rule 1 · 2 · 3

serotonin 1 · 2 · 3

shorthand formulas 1

sigma bonds 1 · 2 · 3

sigmatropic reactions 1 · 2 · 3

[1,2]-shifts 1 · 2 · 3

[1,5]-H-shifts 1 · 2 · 3

[2,3]-shifts 1 · 2

[3,3]-shifts 1 · 2 · 3

silyl ethers 1

Simmons-Smith reagent 1 · 2 · 3

SN2 mechanism (animation) 1 · 2

soap & detergents 1

sodium acetylide 1 · 2 · 3

sodium amide 1 · 2 · 3

sodium borohydride 1 · 2 · 3

sodium triacetoxyborohydride 1 · 2 · 3

solvation of ions 1 · 2 · 3

solvent effects in nmr 1 · 2 · 3

solvents protic & aprotic 1 · 2 · 3

solvolysis 1 · 2 · 3

Sommelet-Hauser rearrangement 1

specific rotation 1 · 2 · 3

Spectroscopy 1 · 2 · 3

absorbance 1 · 2 · 3

infrared spectroscopy 1 · 2 · 3

fingerprint region 1 · 2 · 3

force constant 1 · 2

group frequencies 1 · 2 · 3

alcohol & phenol absorptions 1

alkene absorptions 1

amine absorptions 1 · 2 · 3

arene absorptions 1

carbonyl absorptions 1 · 2 · 3

carboxyl derivative absorptions 1

carboxylic acid absorptions 1

group frequency region 1 · 2 · 3

vibrational states 1 · 2 · 3

wavelength & frequency units 1

mass see mass spectrometry 1 · 2 · 3

molar absorptivity 1 · 2 · 3

nmr spectroscopy 1 · 2 · 3

chemical shift 1 · 2

anisotropy effects 1 · 2 · 3

carbon shift range 1 · 2 · 3

deshielding 1 · 2 · 3

hydrogen bonding influence 1

inductive effect 1 · 2 · 3

isochronous nuclei 1 · 2 · 3

proton shift range 1 · 2 · 3

shielding 1 · 2 · 3

solvent effects 1 · 2 · 3

TMS reference 1 · 2 · 3

CW spectrometer 1 · 2 · 3

deuterated solvents 1

FT spectroscopy 1 · 2 · 3

free induction decay FID 1 · 2 · 3

Larmor frequency 1 · 2

nuclear spin I 1 · 2 · 3

relaxation 1

signal strength 1

spin decoupling 1

spin-spin coupling 1 · 2 · 3

coupling constant J 1 · 2 · 3

first order patterns 1 · 2 · 3

general rules concerning 1 · 2 · 3

Karplus equation 1 · 2 · 3

Pascal triangle 1 · 2 · 3

second order perturbation 1 · 2 · 3

transmittance 1 · 2 · 3

visible & ultraviolet electronic spectroscopy 1 · 2 · 3

chromophore 1 · 2 · 3

conjugated chromophores 1 · 2

electronic excitation 1

empirical rules for calculating absorption 1 · 2 · 3

spectrometer diagram 1 · 2

terminology for absorption shifts e.g. bathochromic 1 · 2 · 3

spin label (supplemental material) 1 · 2

spiro compounds 1 · 2 · 3

stability chemical & thermodynamic 1 · 2

chemical & thermodynamic 1 · 2

staggered conformer 1 · 2

standard state for entropy 1

standard state thermodynamics 1

starch see carbohydrates 1 · 2

stereoelectronic effects 1 · 2 · 3

in addition reactions 1 · 2

in carbonyl reactions 1 · 2 · 3

Cram model 1 · 2 · 3

Felkin-Ahn model 1 · 2 · 3

Karabatsos model 1 · 2

in conformational equilibria 1

in cyclization reactions 1

Baldwin's rules 1

in E2 reactions 1 · 2 · 3

in enolization 1 · 2 · 3

in SN2 reactions 1 · 2 · 3

stereogenic element 1

chiral axis 1

chiral center e.g. asymmetric carbon 1

chiral plane 1

in allenes 1 · 2

stereogenic nitrogen 1

bridged amines & aziridines 1 · 2 · 3

stereoisomer relationship chart 1

stereoisomers 1

stereoselectivity 1

stereoselective addition to double bonds 1

stereoselectivity of carbonyl addition reactions 1 · 2 · 3

stereospecificity 1 · 2 · 3

steric crowding 1

steric effects 1 · 2 · 3

steric hindrance 1 · 2 · 3

in conformational equilibria 1 · 2 · 3

in transition state energy 1 · 2 · 3

of cyclohexyl substituents 1 · 2 · 3

transannular steric strain 1 · 2

steroids see lipids 1

Stetter reaction 1 · 2 · 3

Stevens rearrangement 1 · 2

Stieglitz rearrangement 1 · 2 · 3

Stille coupling 1 · 2 · 3

Stork enamine synthesis 1 · 2 · 3

Stork-Eschenmoser hypothesis 1

strain 1 · 2 · 3

allylic strain 1,2 & 1,3 1 · 2 · 3

angle strain 1 · 2

eclipsing strain torsional strain 1 · 2

torsional strain Pitzer strain 1

structural formulas 1

substituent constants 1

substituent effects in reactions of benzene 1 · 2

substituent effects on carboxylic acid acidity 1 · 2 · 3

substituted cyclohexane conformers 1 · 2

substitution reaction defined 1 · 2 · 3

substitution reaction example 1 · 2 · 3

electrophilic substitution of 5-membered heterocycles 1 · 2 · 3

electrophilic substitution of 6-membered heterocycles 1 · 2 · 3

electrophilic substitution of benzene 1 · 2

nucleophilic substitution of benzene derivatives 1 · 2 · 3

nucleophilic substitution of pyridine 1 · 2 · 3

SN1 & SN2 mechanisms 1 · 2 · 3

sugars see carbohydrates 1 · 2

sulfides (supplemental material) 1 · 2 · 3

sulfonate esters e.g. mesylates and tosylates 1 · 2 · 3

sulfonation of benzene 1 · 2 · 3

sulfonium salts 1 · 2 · 3

sulfur compounds (supplemental material) 1

nucleophilicity 1 · 2

oxidation states 1

ylide formation 1

ylide reaction 1

superbases-nonionic (supplemental material) 1 · 2

suprafacial & antarafaciaL 1 · 2

surfactant 1

Suzuki coupling 1 · 2 · 3

sweetening agents 1

FDA approval of 1

high fructose corn syrup 1

relative sweetness 1

stevia glycosides 1

synthetic sweeteners 1 · 2

Swern oxidation (supplemental material) 1 · 2 · 3

symmetry elements 1

symmetry point groups 1

syn-anti addition 1 · 2 · 3

syn-anti stereo nomenclature (supplemental material) 1 · 2 · 3

syn-eliminations 1 · 2 · 3

synthesis 1

applications of condensation reactions 1

carbon-carbon bond formation 1 · 2

cascade reactions 1 · 2

historical background 1 · 2 · 3

linear vs. convergent 1 · 2 · 3

modern criteria 1 · 2

retrosynthetic analysis 1 · 2 · 3

simple examples 1 · 2 · 3

synthetic transform 1 · 2 · 3

umpolung 1 · 2 · 3

T

tartaric acids 1 · 2

tautomerization defined as a rearrangement 1 · 2 · 3

tautomerism in alkyne hydrations 1 · 2

tautomerization example 1 · 2 · 3

TEMPO a nitroxyl radical 1 · 2 · 3

terpenes see lipids 1 · 2 · 3

rearrangements of terpenes 1 · 2 · 3

tertiary carbon 1 · 2 · 3

testosterone 1 · 2 · 3

tetrahedral configuration 1 · 2 · 3

tetrahydrocannabinol THC 1

thermal cracking 1

thermodynamic stability 1 · 2

thermodynamics 1

thiamine 1 · 2 · 3

ylide-like conjugate base 1 · 2 · 3

thiazolium salts as acyl anion equivalents 1 · 2 · 3

thiols (supplemental material) 1 · 2 · 3

thionyl chloride 1 · 2

characteristics of reactions 1 · 2 · 3

Thorpe-Ingold effect 1

threo-erythro notation (supplemental material) 1 · 2 · 3

tetrose configurations 1 · 2 · 3

Tiffeneau-Demjanov rearrangement 1

Tollens' oxidation 1 · 2 · 3

toxicity 1 · 2

transcription 1

transition metal bonding to alkenes 1 · 2 · 3

transition metal complexes 1

transition metal ligands 1

transition state 1 · 2 · 3

aldol reaction 1 · 2 · 3

E2 mechanism 1 · 2 · 3

electrophilic substitution of benzene derivatives 1 · 2 · 3

SN2 mechanism 1

translation 1

triglycerides see lipids 1

trigonal configuration 1 · 2 · 3

triphenylmethyl radical 1

triphenylphosphine 1 · 2

triphenylphosphine oxide 1 · 2

tropinone 1 · 2 · 3

Truse-Smiles rearrangement 1 · 2 · 3

twist conformer 1 · 2 · 3

two or more stereogenic centers 1 · 2 · 3

U

ultraviolet-visible spectroscopy see Spectroscopy 1

V

valence 1 · 2

valence electrons 1 · 2 · 3

valence octet 1 · 2 · 3

valence of common elements 1 · 2 · 3

valence shell 1 · 2 · 3

van der Waals attraction 1 · 2

vanillin 1 · 2

vicinal 1 · 2

viewing rule 1

Vilsmeier reagent 1

vinyl group 1 · 2 · 3

vinyl cation (carbocation stability order) 1 · 2 · 3

vinyl compounds 1 · 2 · 3

vinylagous systems 1 · 2

acidic hydroxyl compounds also vinylagous esters and amides 1 · 2

conjugate addition 1 · 2

β-elimination 1

Michael reaction 1

(supplemental material) 1

vinylagous activation of C-H 1

vitamin C 1

vitamin D photochemistry 1

vitamins A, D, E & K 1 · 2

Vollardt trimerization 1 · 2 · 3

VSEPR 1

vulcanization of rubber 1 · 2

W

Wagner-Meerwein rearrangement 1 · 2 · 3

water solubility 1

wavelength 1 · 2

wedge-shaped bonds 1 · 2 · 3

Weiss reaction 1 · 2 · 3

Wilkinson's catalyst 1 · 2

the Wittig reaction 1

Wolff rearrangement 1 · 2

Wolff-Kishner reduction 1 · 2 · 3

Woodward-Fieser rules for calculating UV absorption 1 · 2

Wöhler, F. (urea synthesis) 1

X

xanthate pyrolysis 1 · 2 · 3

Y

ylides 1

reactions of phosphorous ylides 1 · 2

reactions of sulfur ylides 1

Z

Zaitsev rule 1 · 2

zig-zag configurational formulas (supplemental material) 1

zinc alkyl reagents 1 · 2 · 3

zinc-copper couple 1

zwitterion form of amino acids 1