Reaction Finder for The Organic ChemIST


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acetal acetoacetic acetone acetylide acid
acid-catalyzed acidic acids acyl acylation
addition 1,2-addition 1,4-addition adds Ag+/NH3
alcohol aldaric aldehyde alditol alditols
aldol aldonic aldose aldoses alkane
alkene cis-alkene trans-alkene alkylation alkyne
allylic a alternative amide amination
ammonium anhydride aniline annulation anti-Markovnikov
applications ArBr ArCHOH ArCl ArCN
arenediazonium ArF ArH ArI ArN2
ArN2Ar ArNH2 ArNO2 ArOH aromatic
ArR ArSO3H autoxidation Baeyer–Villiger base-catalyzed
bases basic benzene benzoquinone benzylic
benzyne bimolecular borane bromination a-bromination
2-bromobutane N-bromosuccinimide bulky n-butane tri-tert-butoxyaluminum
byproduct C–C can carbon carbonates
carbonyl carboxylic catalysis catalytic chain
chloride chlorination chlorochromate chromium(VI) Cl2
Claisen cleavage Clemmensen CN– condensation
conditions configuration conjugate conversion Cope
copper(I) crossed) crown cuprate cyanide
cyanohydrin cycloalkane cyclohexane cyclopropane decarboxylation
decomposition degradation dehydration deprotonated desulfonation
dialkyl diazomethane dibromide dicarboxylic Dieckmann
Diels–Alder diene diisobutylaluminum 1,2-diketone diol
1,2-dione dioxide 1,3-dioxo direct dissolving
disulfide DMSO/oxalyl E2 elimination elongation
enamine enhance enolate epoxidation epoxide
epoxides equilibrium equivalents ether ethers
excess exhaustive extreme F– Fischer
fluorides fluoroboric formation Fremy Friedel–Crafts
furan Gabriel gas general Gilman
glycoside N-glycoside Grignard H2O2 H2SO4
halide halidel haloform halogen a-halogenation
halohydrin harsh HBr HCl Hell–Vollhard–Zelinski
hindered HO– Hofmann hydrate hydrazine
hydrazone hydroboration–oxidation hydrogen hydrogenation a-hydrogens
hydrolysis hydroquinone hydrosulfide a-hydroxy b-hydroxy
hydroxylamine hypophosphorous I– imine industrial
internal intramolecular inversion iodide iodination
isolated ketal keto–enol b-ketocarboxylic b-ketoester
ketone ketones ketose Kiliani–Fischer kinetic
leaving limited lithium made malonic
Markovnikov mechanism methyl Michael mild
mixed mixture monosaccharide NaBr NaSH
needed neutral nitrate nitration nitrile
nitro non-Zaitsev nucleophile nucleophilicity opening
organocopper organometallic osazone oxidative oxime
oxymercuration–demercuration ozone periodic permanganate peroxide
peroxides phase phenol POCl3 position
b-position potasium potassium precipitate primary
protecting protonated pyranoses pyridinium pyrrolidine
quaternary R2C=O R2CuLi R2N(CH3)2+I– R2NH
R2S R3N R3NCH3+I– R3NO R4N+
R4N+I– R4N+X– radical RBr RCH2CH2R
RCHO RCl RCN RCO2H RCO2R
RCOC reagent rearrangements reduction reductive
regiochemical removal results retention reversible
RF RH RI ring RMgBr
RN(CH3)3+ RN(CH3)3+I– RN3 RNH2 Robinson
ROCH2R ROH ROOH ROOR ROR
Rosenmund ROTs RS– RSH RSR
RSSR Ruff RX salt Sandmeyer
Schiemann Schiff secondary selective semicarbazide
semicarbazone shortening silver(I) Simmons-Smith SN1
SN2 SN2 SO2 SOCl2 specific
starting stereospecific Stork strained strongly
substituted substitution substrate sulfonation Swern
synthesis temperature terminal tertiary thermodynamic
thioacetal thioketal thiol thionyl Tollens
p-toluenesulfonic tosylate transesterification TsCl TsO–
under used vicinal vinylic water
weakly Wittig Wolff–Kishner work-up Zaitsev
zinc Zn(Hg)
Reactions of Alkenes
acid-catalyzed addition alcohol alkene a
anti-Markovnikov chloride conditions cyclopropane elimination
H2O2 H2SO4 halide halogen harsh
hydroboration–oxidation hydrogen hydrogenation Markovnikov opening
oxymercuration–demercuration peroxide radical RBr RCl
RH RI ROH ROOR ROR
Simmons-Smith water
Reactions of Alkynes
acetylide addition aldehyde alkane alkene
cis-alkene trans-alkene alkylation alkyne anti-Markovnikov
basic borane cleavage conditions 1,2-diketone
formation H2O2 halide halogen hindered
hydroboration–oxidation hydrogen hydrogenation internal ketone
ketones Markovnikov methyl neutral permanganate
peroxide R2C=O radical RBr RCH2CH2R
RCHO RCl RCO2H results RH
RI ROOR terminal under water
Reactions of Dienes
addition alkene C–C Diels–Alder diene
HCl isolated kinetic RBr RCl
temperature thermodynamic
Reactions of Alkanes
alkene allylic bromination 2-bromobutane N-bromosuccinimide
n-butane chlorination Cl2 cycloalkane HBr
hydrogenation radical RBr RCl RH
selective strained
Substitution Reactions of Alkyl Halides
acetone acetylide alkene alkyl alkyne
ammonium byproduct C–C can crown
enhance epoxide ether F– formation
halide halohydrin made NaBr nucleophilicity
precipitate primary quaternary R2N(CH3)2+I– R2NH
R3N R3NCH3+I– R4N+I– RBr RCl
RCN RCO2R RF RI RN(CH3)3+I–
RN3 RNH2 ROH ROR RSH
RSR RX salt secondary SN1
SN2 starting tertiary used
Elimination Reactions of Alkyl Halides
alkene alkyne bases bulky dibromide
E2 elimination fluorides mechanism non-Zaitsev
RBr RCl reduction RF RI
ROTs RX vicinal Zaitsev
Reactions of Alcohols, Amines, and Related Compounds
acetylide acid acidic alcohol alkane
alkene alkyl alkyne allylic amine
applications autoxidation bimolecular byproduct C–C
carbon catalysis chloride CN– conditions
configuration Cope dehydration disulfide elimination
epoxide epoxides ether ethers formation
gas general halide harsh HCl
HO– Hofmann hydrosulfide I– industrial
inversion leaving limited mild NaSH
non-Zaitsev nucleophilic opening organocopper organometallic
peroxides phase POCl3 position protonated
R2CuLi R2NH R2S R3N R3NO
R4N+ R4N+X– RBr RCl RCN
reagent rearrangements reduction retention RF
RI RMgBr RN(CH3)3+ RN(CH3)3+I– RNH2
ROCH2R ROH ROOH ROOR ROR
ROTs RS– RSH RSR RSSR
RX SN2 SO2 SOCl2 specific
substituted substitution thiol thionyl p-toluenesulfonic
tosylate TsCl TsO– vinylic water
zinc
Aromatic Compounds
acylation alkylation ArBr ArCl ArH
ArI ArNO2 ArR ArSO3H benzene
bromination chlorination Clemmensen desulfonation Friedel–Crafts
hydrazine iodination nitration R2C=O RCHO
reduction RH sulfonation Wolff–Kishner Zn(Hg)
Reactions of Substituted Benzenes
acid alcohol alkyl amine ammonium
aniline ArBr ArCHOH ArCl ArCN
arenediazonium ArF ArH ArI ArN2
ArN2Ar ArNH2 ArNO2 ArOH aromatic
benzene benzylic benzyne bromide bromination
N-bromosuccinimide catalytic chloride conditions copper(I)
cyanide cyclohexane Diels–Alder extreme fluoroboric
formation furan harsh hydrogenation hypophosphorous
iodide mild nitrate nitrile nitro
oxidation phenol potasium primary R2C=O
RBr RCN RCO2H reduction RH
RNH2 salt Sandmeyer Schiemann selective
sulfide water
Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
acid acyl addition adds alcohol
alkyl amide amine ammonium anhydride
bromide carboxylic chloride conversion cuprate
decomposition dehydration dialkyl diazomethane dicarboxylic
Fischer formation Gabriel Grignard halide
Hofmann hydrolysis ketone lithium nitrile
nucleophilic primary R2C=O RBr RCl
RCN RCO2H RCO2R rearrangement RNH2
ROH salt substitution synthesis tertiary
transesterification
Reactions of Aldehydes and Ketones
acetal acetylide acid acyl addition
1,2-addition 1,4-addition adds alcohol aldehyde
alkane alkene alkyne alternative amide
amination are base basic tri-tert-butoxyaluminum
carbon chloride CO2 conjugate cyanide
diisobutylaluminum dioxide direct enamine equivalents
ester formation Gilman Grignard halide
hydrate hydrazine hydrazone hydride hydrogenation
a-hydroxy b-hydroxy hydroxylamine imine ketal
ketone lithium needed nitrile nucleophile
oxime primary protecting R2C=O R2NH
R3N RBr RCHO RCl RCN
RCO2H RCO2R reagent reduction reductive
removal reversible RH RNH2 ROH
ROR RSR Schiff secondary semicarbazide
semicarbazone strongly substitution synthesis tertiary
thioacetal thioketal weakly Wittig Wolff–Kishner
Oxidation and Reduction of Organic Compounds
acid acids acyl Ag+/NH3 alcohol
aldehyde alkene alkyne amine aromatic
Baeyer–Villiger base benzoquinone carboxylic chloride
chlorochromate chromium(VI) cleavage diol 1,2-dione
dissolving DMSO/oxalyl epoxidation epoxide ester
formation Fremy halide hydride hydrogenation
hydroquinone imine ketone metal oxidation
oxidative ozone periodic permanganate potassium
primary pyridinium R2C=O R2NH RCHO
RCO2H reagent reduction reductive RH
ring ROH Rosenmund salt Schiff
secondary selective silver(I) stereospecific substituted
Swern Tollens work-up
Reactions Involving Enols, Enolates, and Related Species
acetoacetic acetylide acidic acyl acylation
addition adds alcohol aldol alkene
alkylation alkyne annulation base basic
bromide a-bromination C–C carbonates carbonyl
carboxylic Claisen CN– condensation conditions
conjugate crossed) decarboxylation deprotonated Dieckmann
1,3-dioxo E2 elimination enamine enolate
equilibrium equivalents ester excess exhaustive
halidel haloform a-halogenation Hell–Vollhard–Zelinski hydrazone
a-hydrogens hydrolysis intramolecular keto–enol b-ketocarboxylic
b-ketoester malonic Michael mixed b-position
pyrrolidine R2C=O RBr RCHO RCl
RCN RCO2H RCO2R RCOC regiochemical
RH RI Robinson ROH ROR
RSR RX selective SN2 Stork
substrate synthesis
Carbohydrates
acid acid-catalyzed acylation aldaric alditol
alditols aldonic aldose aldoses alkylation
anhydride base-catalyzed chain cleavage cyanohydrin
degradation elongation equilibrium formation glycoside
N-glycoside ketose Kiliani–Fischer mixture monosaccharide
opening osazone oxidation oxidative pyranoses
R2C=O R2NH RCHO RCN RCO2H
RCO2R reagent reduction RNH2 ROH
ROR Ruff RX shortening synthesis
Tollens