There are several important name reactions in organic chemistry, called such because they either bear the names of the persons who described them or else are called by a specific name in texts and journals. Sometimes the name offers a clue about the reactants and products, but not always. Here are the names and equations for key reactions, listed in alphabetical order.
- Acetoacetic-Ester Condensation Reaction
- Acetoacetic Ester Synthesis
- Acyloin Condensation
- Alder-Ene Reaction or Ene Reaction
- Aldol Reaction or Aldol Addition
- Aldol Condensation Reaction
- Appel Reaction
- Arbuzov Reaction or Michaelis-Arbuzov Reaction
- Arndt-Eistert Synthesis Reaction
- Azo Coupling Reaction
- Baeyer-Villiger Oxidation - Named Organic Reactions
- Baker-Venkataraman Rearrangement
- Balz-Schiemann Reaction
- Bamford-Stevens Reaction
- Barton Decarboxylation
- Barton Deoxygenation Reaction - Barton-McCombie Reaction
- Baylis-Hillman Reaction
- Beckmann Rearrangement Reaction
- Benzilic Acid Rearrangement
- Benzoin Condensation Reaction
- Bergman Cycloaromatization - Bergman Cyclization
- Bestmann-Ohira Reagent Reaction
- Biginelli Reaction
- Birch Reduction Reaction
- Bicschler-Napieralski Reaction - Bicschler-Napieralski Cyclization
- Blaise Reaction
- Blanc Reaction
- Bohlmann-Rahtz Pyridine Synthesis
- Bouveault-Blanc Reduction
- Brook Rearrangement
- Brown Hydroboration
- Bucherer-Bergs Reaction
- Buchwald-Hartwig Cross Coupling Reaction
- Cadiot-Chodkiewicz Coupling Reaction
- Cannizzaro Reaction
- Chan-Lam Coupling Reaction
- Crossed Cannizzaro Reaction
- Friedel-Crafts Reaction
- Huisgen Azide-Alkyne Cycloaddition Reaction
- Itsuno-Corey Reduction - Corey-Bakshi-Shibata Readuction
- Seyferth-Gilbert Homologation Reaction
Acetoacetic-Ester Condensation Reaction
The acetoacetic-ester condensation reaction converts a pair of ethyl acetate (CH3COOC2H5) molecules into ethyl acetoacetate (CH3COCH2COOC2H5) and ethanol (CH3CH2OH) in the presence of sodium ethoxide (NaOEt) and hydronium ions (H3O+).
Acetoacetic Ester Synthesis
In this organic name reaction, the acetoacetic ester synthesis reaction converts a α-keto acetic acid into a ketone.
The most acidic methylene group reacts with the base and attaches the alkyl group in its place.
The product of this reaction can be treated again with the same or different alkylation agent (the downward reaction) to create a dialkyl product.
The acyloin condensation reaction joins two carboxylic esters in the presence of sodium metal to produce a α-hydroxyketone, also known as a acyloin.
The intramolecular acyloin condensation can be used to close rings as in the second reaction.
Alder-Ene Reaction or Ene Reaction
The Alder-Ene reaction, also known as the Ene reaction is a group reaction which combines an ene and enophile. The ene is an alkene with an allylic hydrogen and the enophile is a multiple bond. The reaction produces an alkene where the double bond is shifted to the allylic position.
Aldol Reaction or Aldol Addition
The aldol addition reaction is the combination of an alkene or ketone and the carbonyl of another aldehyde or ketone to form a β-hydroxy aldehyde or ketone.
Aldol is a combination of the terms 'aldehyde' and 'alcohol.'
Aldol Condensation Reaction
The aldol condensation removes the hydroxyl group formed by the aldol addition reaction in the form of water in the presence of a acid or base.
The aldol condensation forms α,β-unsaturated carbonyl compounds.
The Appel reaction converts an alcohol to an alkyl halide using triphenylphosphine (PPh3) and either tetrachloromethane (CCl4) or tetrabromomethane (CBr4).
Arbuzov Reaction or Michaelis-Arbuzov Reaction
The Arbuzov or Michaelis-Arbuzov reaction combines a trialkyl phosphate with an alkyl halide (The X in the reaction is a halogen) to form an alkyl phosphonate.
Arndt-Eistert Synthesis Reaction
The Arndt-Eistert synthesis is a progression of reactions to create a carboxylic acid homologue.
This synthesis adds a carbon atom to an existing carboxylic acid.
Azo Coupling Reaction
The azo coupling reaction combines diazonium ions with aromatic compounds to form azo compounds.
Azo coupling is commonly used to create pigments and dyes.
Baeyer-Villiger Oxidation - Named Organic Reactions
The Baeyer-Villiger oxidation reaction converts a ketone into an ester. This reaction requires the presence of a peracid such as mCPBA or peroxyacetic acid. Hydrogen peroxide can be used in conjunction with a Lewis base to form a lactone ester.
The Baker-Venkataraman rearrangement reaction converts an ortho-acylated phenol ester into a 1,3-diketone.
The Balz-Schiemann reaction is a method to convert aryl amines by diazotisation to aryl fluorides.
The Bamford-Stevens reaction converts tosylhydrazones into alkenes in the presence of a strong base.
The type of alkene depends on the solvent used. Protic solvents will produce carbenium ions and aprotic solvents will produce carbene ions.
The Barton decarboxylation reaction converts a carboxylic acid into a thiohydroxamate ester, commonly called a Barton ester, and then reduced into the corresponding alkane.
- DCC is N,N'-dicyclohexylcarbodiimide
- DMAP is 4-dimethylaminopyridine
- AIBN is 2,2'-azobisisobutyronitrile
Barton Deoxygenation Reaction - Barton-McCombie Reaction
The Barton deoxygenation reaction removes the oxygen from alkyl alcohols.
The hydroxy group is replaced by a hydride to form a thiocarbonyl derivative, which is then treated with Bu3SNH, which carries away everything except the desired radical.
The Baylis-Hillman reaction combines an aldehyde with an activated alkene. This reaction is catalyzed by a tertiary amine molecule such as DABCO (1,4-Diazabicyclo[2.2.2]octane).
EWG is an Electron Withdrawing Group where electrons are withdrawn from aromatic rings.
Beckmann Rearrangement Reaction
The Beckmann rearrangement reaction converts oximes into amides.
Cyclic oximes will produce lactam molecules.
Benzilic Acid Rearrangement
The benzilic acid Rearrangement reaction rearranges a 1,2-diketone into an α-hydroxycarboxylic acid in the presence of a strong base.
Cyclic diketones will contract the ring by the benzilic acid rearrangement.
Benzoin Condensation Reaction
The benzoin condensation reaction condenses a pair of aromatic aldehydes into an α-hydroxyketone.
Bergman Cycloaromatization - Bergman Cyclization
The Bergman cycloaromatization, also known as the Bergman cyclization, creates enediyenes from substituted arenes in the presence of a proton donor like 1,4-cyclohexadiene. This reaction can be initiated by either light or heat.
Bestmann-Ohira Reagent Reaction
The Bestmann-Ohira reagent reaction is a special case of the Seyferth-Gilbert homolgation reaction.
The Bestmann-Ohira reagent uses dimethyl 1-diazo-2-oxopropylphosphonate to form alkynes from an aldehyde.
THF is tetrahydrofuran.
The Biginelli reaction combines ethyl acetoacetate, an aryl aldehyde, and urea to form dihydropyrimidones (DHPMs).
The aryl aldehyde in this example is benzaldehyde.
Birch Reduction Reaction
The Birch reduction reaction converts aromatic compounds with benzenoid rings into 1,4-cyclohexadienes. The reaction takes place in ammonia, an alcohol and in the presence of sodium, lithium or potassium.
Bicschler-Napieralski Reaction - Bicschler-Napieralski Cyclization
The Bicschler-Napieralski reaction creates dihydroisoquinolines through the cyclization of β-ethylamides or β-ethylcarbamates.
The Blaise reaction combines nitriles and α-haloesters using zinc as a mediator to form β-enamino esters or β-keto esters. The form the product produces depends on the addition of the acid.
THF in the reaction is tetrahydrofuran.
The Blanc reaction produces chloromethylated arenes from an arene, formaldehyde, HCl, and zinc chloride.
If the concentration of the solution is high enough, a secondary reaction with the product and the arenes will follow the second reaction.
Bohlmann-Rahtz Pyridine Synthesis
The Bohlmann-Rahtz pyridine synthesis creates substituted pyridines by condensing enamines and ethynylketones into an aminodiene and then a 2,3,6-trisubstituted pyridine.
The EWG radical is an electron withdrawing group.
The Bouveault-Blanc reduction reduces esters to alcohols in the presence of ethanol and sodium metal.
The Brook rearrangement transports the silyl group on an α-silyl carbinol from a carbon to the oxygen in the presence of a base catalyst.
The Brown hydroboration reaction combines hydroborane compounds to alkenes. The boron will bond with the least hindered carbon.
The Bucherer-Bergs reaction combines a ketone, potassium cyanide, and ammonium carbonate to form hydantoins.
The second reaction shows a cyanohydrin and ammonium carbonate forms the same product.
Buchwald-Hartwig Cross Coupling Reaction
The Buchwald-Hartwig cross coupling reaction forms aryl amines from aryl halides or pseudohalides and primary or secondary amines using a palladium catalyst.
The second reaction shows the synthesis of aryl ethers using a similar mechanism.
Cadiot-Chodkiewicz Coupling Reaction
The Cadiot-Chodkiewicz coupling reaction creates bisacetylenes from the combination of a terminal alkyne and an alkynyl halide using a copper(I) salt as a catalyst.
The Cannizzaro reaction is a redox disproportionation of aldehydes to carboxylic acids and alcohols in the presence of a strong base.
The second reaction uses a similar mechanism with α-keto aldehydes.
The Cannizzaro reaction sometimes produces unwanted byproducts in reactions involving aldehydes in basic conditions.
Chan-Lam Coupling Reaction
The Chan-Lam coupling reaction forms aryl carbon-heteroatom bonds by combining arylboronic compounds, stannanes, or siloxanes with compounds containing either a N-H or O-H bond.
The reaction uses a copper as a catalyst which can be reoxidized by oxygen in the air at room temperature. Substrates can include amines, amides, anilines, carbamates, imides, sulfonamides, and ureas.
Crossed Cannizzaro Reaction
The crossed Cannizzaro reaction is a variant of the Cannizzaro reaction where formaldehyde is a reducing agent.
A Friedel-Crafts reaction involves the alkylation of benzene.
When a haloalkane is reacted with benzene using a Lewis acid (commonly an aluminum halide) as a catalyst, it will attach the alkane to the benzene ring and produce excess hydrogen halide.
It is also called Friedel-Crafts alkylation of benzene.
Huisgen Azide-Alkyne Cycloaddition Reaction
The Huisgen Azide-Alkyne cycloaddition combines an azide compound with an alkyne compound to form a triazole compound.
The first reaction requires only heat and forms 1,2,3-triazoles.
The second reaction uses a copper catalyst to form only 1,3-triazoles.
The third reaction uses a ruthenium and cyclopentadienyl (Cp) compound as a catalyst to form 1,5-triazoles.
Itsuno-Corey Reduction - Corey-Bakshi-Shibata Readuction
The Itsuno-Corey Reduction, also known as the Corey-Bakshi-Shibata Readuction (CBS reduction for short) is an enantioselective reduction of ketones in the presence of a chiral oxazaborolidine catalyst (CBS catalyst) and borane.
THF in this reaction is tetrahydrofuran.
Seyferth-Gilbert Homologation Reaction
The Seyferth-Gilbert homologation reacts aldehydes and aryl ketones with dimethyl (diazomethyl)phosphonate to synthesize alkynes at low temperatures.
THF is tetrahydrofuran.
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