Organic reactions are chemical reactions between organic compounds.

The number of possible organic reactions is basically infinite. However, certain general patterns are observed that can be used to describe many common or useful reactions. Each reaction has a stepwise mechanism that says how it happens, although this detailed description of steps is not always clear from a list of reactants alone.

Organic reactions can be organized into several basic types:

Some reactions fit into more than one category. For example, some substitution reactions follow an addition elimination pathway.

Here are some common reactions that you may run into in a college organic chemistry course: addition of HX to an alkene, halogen addition reaction, halohydrin formation reaction, oxymercuration reaction, hydroboration-oxidation reaction, hydrooxylation reaction, ozonolysis reaction, nucleophilic substitution, halogenation of an alkyl, hydration and dehydration.

Here is a series of reactions that a chemist can perform to change molecules in a defined way: Beckmann rearrangement, Friedel-Crafts alkylation and acylation, Gilman reagent, Grignard reagent, Diels-Alder reaction, Pinner reaction, Sharpless epoxidation, Sharpless bishydroxylation, Swern oxidation

As seen here, specific reactions are sometimes named after the chemist who developed them.

(When adding to this page, if a reaction has a common name, please include it at the BEGINNING of the line, for consistency. If the reaction consists of multiple steps, include all steps on a single line, separated by a semicolon.)

Reactions of aliphatic compounds

Hydrocarbons

Alkanes

Free radical halogenation: alkane + X2 --> alkyl halide + HX
Combustion: alkane + O2 --> CO2 + H2O + heat
Cracking

Alkenes, Dienes, and Alkynes

Hydrocarbons plus Group 15 (Pnictogen)

Nitrogen containing compounds

Amines

Imines

Synthesis by nucleophilic addition: (1) ketone or aldehyde + ammonia or primary amine ↔ tetrahedral carbonyl addition compound; (2) tetrahedral carbonyl addition compound + acid (catalyst) ↔ imine + water
Nucleophilic addition: (1) imine + ammonia or primary amine ↔ tetrahedral imine addition compound; (2) tetrahedral imine addition compound + acid (catalyst) ↔ new imine
Hydrolysis: Opposite of synthesis

Phosphorus containing compounds

Hydrocarbons plus Group 16 (Chalcogen)

Oxygen containing compounds

Alcohols

Transesterification

Ethers

2 alcohol → ether
Williamson ether synthesis: alkoxide + alkyl halide → ether
alkene + alcohol + acid catalyst → ether

Epoxides

Carbonyl derivatives

Carboxylic acids

Carboxyl groups also react with amine groups to form peptide bonds and with alcohols to form esters
Carboxylic acids can be reduced by LiAlH4 to form primary alcohols

Ketones

Synthesis: Ketones can be created by oxidation of secondary alcohols. The process requires a strong oxidising agent such as potassium dichromate or other reagent containing Cr(VI). The alcohol is oxidised by heating under reflux in acidified solution. For example 2-propanol is oxidised to propanone (acetone):; H₃C-CH(OH)-CH₃ → H₃C-CO-CH₃; Two atoms of hydrogen are removed, leaving a single oxygen atom double bonded to a carbon atom.
Nucleophilic addition: ketone + anion of terminal alkyne → tetrahedral carbonyl addition compound (alkoxide); alkoxide + aqueous acid → hydroxyalkyne
Nucleophilic addition: ketone + ammonia or primary amine ↔ tetrahedral carbonyl addition compound; tetrahedral carbonyl addition compound + acid catalyst → imine + water
Nucleophilic addition: ketone + secondary amine ↔ tetrahedral carbonyl addition compound; tetrahedral carbonyl addition compound + acid catalyst → enamine + water
Nucleophilic addition: ketone + Grignard reagent → magnesium alkoxide; magnesium alkoxide + aqueous acid → tertiary alcohol
Nucleophilic addition: ketone + organolithium reagent → lithium alkoxide; lithium alkoxide + aqueous acid → tertiary alcohol
Nucleophilic addition: ketone + alcohol + acid or base ↔ hemiacetal + water; hemiacetal + alcohol + acid catalyst ↔ acetal + water; This is a carbonyl-protecting reaction.
Electrophilic addition: ketone + electrophile → resonance stabilized cation
Wittig reaction: ketone + phosphonium ylide → oxphosphetane; oxphosphetane → phosphine oxide + alkene
ketone + water ↔ geminal diol
ketone + thiol + acid catalyst ↔ thioacetal + water
ketone + hydrazine or derivative of hydrazine → hydrazone
ketone + metal hydride → metal alkoxide salt; metal alkoxide salt + water → alcohol
Keto-enol tautomerism: ketone + acid catalyst ↔ enol; enol + halogen → α-haloketone
Reactions at an α-carbon: ketone + aqueous deuterium + D⁺ or OD^- catalyst → ketone-d + HOD
Wolff-Kishner reaction: ketone group + hydrazine ↔ methyl group
Clemmensen reduction: ketone group + Zn(Hg), HCl ↔ methyl group

Aldehydes

Synthesis: Reacting a primary alcohol with some oxidizing agents, such as pyridinium chloride, yields an aldehyde.
Synthesis: Reacting an alkene with ozone will cause the bond to break if there is a vinylic hydrogen.
Synthesis: Reacting an ester with DIBAH can cause reduction, yielding an aldehyde.
aldehyde + alcohol + acid or base ---> hemiacetal; hemiacetal + alcohol + acid catalyst ---> acetal + water;
Treating aldehydes with oxidizing agents such as potassium permanganate, nitric acid, or chromium oxide, will yield a carboxylic acid.
Treating aldehydes with Tollens' reagent (Ag₂O in aqueous ammonia) will convert aldehydes to carboxylic acids without attacking carbon-carbon double bonds.
Aldehydes can react with water to form geminal diols.
Aldehydes can react with HCN to form cyanohydrins, R-C(H)(OH)(CN).
Treating an aldehyde with a Grignard reagent can yield an alcohol with a substituted group from the Grignard reagent.
Wolff-Kishner reaction: Treating aldehydes with hydrazine will reduce a C=O bond to CH₂.
Nucleophilic addition: aldehyde + nucleophile ---> tetrahedral carbonyl addition compound; aldehyde + ammonia or primary amine ---> tetrahedral carbonyl addition compound; tetrahedral carbonyl addition compound + acid (catalyst) ---> imine + water
Aldehydes are oxidized to carboxylic acids.
Aldehydes are reduced to primary alcohols.

Organic reaction

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