Reaction reference

Organic Reaction Guides and Chemical Reaction Drawer

Fast reference pages for highly searched organic reactions. Each guide includes a concise scheme, two common examples, reaction SMILES, key conditions, and an edit-in-MolDraw button. Use the chemical reaction drawer to sketch reactants, products, arrows, reagents, and conditions online.

Aldol condensation

Carbonyl enolate addition followed by dehydration to form alpha,beta-unsaturated carbonyl compounds.

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Wittig reaction

Conversion of aldehydes or ketones to alkenes using phosphonium ylides.

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Grignard reaction

Carbon-carbon bond formation using organomagnesium reagents and carbonyl electrophiles.

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Suzuki coupling

Palladium-catalyzed coupling of aryl halides and boronic acids to form biaryls.

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Heck reaction

Palladium-catalyzed arylation or vinylation of alkenes.

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Friedel-Crafts acylation

Electrophilic aromatic substitution that installs an acyl group on an aromatic ring.

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Diels-Alder reaction

Concerted cycloaddition between a conjugated diene and dienophile to form cyclohexenes.

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Name reactions

Name reactions with full mechanisms

Every curly-arrow step, checked electron by electron, with conditions, JEE/NEET notes and a button that opens the complete mechanism in MolDraw.

Reimer–Tiemann Reaction

The Reimer–Tiemann reaction turns phenol into salicylaldehyde (2-hydroxybenzaldehyde) with chloroform and aqueous sodium hydroxide.

Mechanism guide

Kolbe–Schmitt Reaction

In the Kolbe–Schmitt reaction (often called the Kolbe reaction in Indian syllabuses) sodium phenoxide is heated with carbon dioxide under pressure.

Mechanism guide

Hofmann Bromamide Reaction

The Hofmann bromamide reaction converts a primary amide into a primary amine with one carbon fewer, using bromine and sodium hydroxide.

Mechanism guide

Sandmeyer Reaction

The Sandmeyer reaction replaces the diazonium group of an arenediazonium salt by Cl, Br or CN using the copper(I) salt.

Mechanism guide

Gabriel Phthalimide Synthesis

The Gabriel synthesis makes pure primary amines.

Mechanism guide

Williamson Ether Synthesis

The Williamson ether synthesis makes ethers by an SN2 reaction between an alkoxide (or phenoxide) and a methyl or primary alkyl halide.

Mechanism guide

Cannizzaro Reaction

In the Cannizzaro reaction an aldehyde without α-hydrogens (HCHO, benzaldehyde, pivalaldehyde) disproportionates in concentrated base: one molecule is oxidised to the carboxylate and another is reduced to the alcohol.

Mechanism guide

Wolff–Kishner Reduction

The Wolff–Kishner reduction converts the C=O of an aldehyde or ketone into CH₂.

Mechanism guide

Hell–Volhard–Zelinsky Reaction

The Hell–Volhard–Zelinsky (HVZ) reaction brominates a carboxylic acid at the α-carbon.

Mechanism guide

Iodoform (Haloform) Reaction

Methyl ketones (CH₃CO–) and alcohols that oxidise to them (CH₃CH(OH)–) react with iodine and sodium hydroxide to give a yellow precipitate of iodoform, CHI₃.

Mechanism guide

Diazotization Reaction

Diazotization converts a primary aromatic amine into an arenediazonium salt with sodium nitrite and a mineral acid at 0–5 °C.

Mechanism guide

Azo Coupling Reaction

In azo coupling an arenediazonium ion acts as a weak electrophile towards strongly activated rings — phenoxides and anilines.

Mechanism guide

Claisen Condensation

The Claisen condensation joins two ester molecules into a β-keto ester.

Mechanism guide

Beckmann Rearrangement

In the Beckmann rearrangement a ketoxime is converted into an amide by acid (H₂SO₄, PCl₅, SOCl₂, polyphosphoric acid).

Mechanism guide

Pinacol–Pinacolone Rearrangement

Pinacol (2,3-dimethylbutane-2,3-diol) rearranges in acid to pinacolone (3,3-dimethylbutan-2-one).

Mechanism guide

Baeyer–Villiger Oxidation

The Baeyer–Villiger oxidation inserts an oxygen atom between a carbonyl carbon and one of its neighbours, turning ketones into esters and cyclic ketones into lactones.

Mechanism guide

Benzoin Condensation

In the benzoin condensation two molecules of an aromatic aldehyde join to form an α-hydroxy ketone (benzoin) under catalysis by cyanide.

Mechanism guide

Hydroboration–Oxidation

Hydroboration–oxidation converts an alkene into an alcohol with the OH on the less substituted carbon (anti-Markovnikov) and with syn addition of H and OH.

Mechanism guide

Ozonolysis

Ozonolysis cleaves a carbon–carbon double bond into two carbonyl groups.

Mechanism guide

Swern Oxidation

The Swern oxidation turns primary alcohols into aldehydes and secondary alcohols into ketones without over-oxidation or heavy metals.

Mechanism guide

Mitsunobu Reaction

The Mitsunobu reaction converts an alcohol into an ester (or ether, imide, azide) with clean inversion at the alcohol carbon.

Mechanism guide

Curtius Rearrangement

In the Curtius rearrangement an acyl azide loses nitrogen on heating while its R group moves from carbon to nitrogen, giving an isocyanate.

Mechanism guide

Friedel–Crafts Alkylation

Friedel–Crafts alkylation attaches an alkyl group to an aromatic ring using an alkyl halide and a Lewis acid such as AlCl₃.

Mechanism guide

Michael Addition

The Michael addition is the conjugate (1,4-) addition of a stabilised carbanion — a malonate, β-keto ester or nitroalkane anion — to the β-carbon of an α,β-unsaturated carbonyl compound.

Mechanism guide