Amide

Organic compounds of the form RC(=O)NR′R″

This article is about organic amides with the formula RC(=O)NR′R″. For the anion NH−2, see Azanide. For other uses, see Amide (functional group).

Not to be confused with imide.

General structure of an amide (specifically, a carboxamide) Formamide, the simplest amide Asparagine (zwitterionic form), an amino acid with a side chain (highlighted) containing an amide group

In organic chemistry, an amide,[1][2][3] also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms.[4][5] The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid (R−C(=O)−OH) with the hydroxyl group (−OH) replaced by an amino group (−NR′R″); or, equivalently, an acyl (alkanoyl) group (R−C(=O)−) joined to an amino group.

Common amides are formamide (H−C(=O)−NH2), acetamide (H3C−C(=O)−NH2), benzamide (C6H5−C(=O)−NH2), and dimethylformamide (H−C(=O)−N(−CH3)2). Some uncommon examples of amides are N-chloroacetamide (H3C−C(=O)−NH−Cl) and chloroformamide (Cl−C(=O)−NH2).

Amides are qualified as primary, secondary, and tertiary according to the number of acyl groups bounded to the nitrogen atom.[5][6]

## Nomenclature

[edit]

Main article: IUPAC nomenclature of organic chemistry § Amines and amides

The core −C(=O)−(N) of amides is called the amide group (specifically, carboxamide group).

In the usual nomenclature, one adds the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH3CONH2). IUPAC recommends ethanamide, but this and related formal names are rarely encountered. When the amide is derived from a primary or secondary amine, the substituents on nitrogen are indicated first in the name. Thus, the amide formed from dimethylamine and acetic acid is N,N-dimethylacetamide (CH3CONMe2, where Me = CH3). Usually even this name is simplified to dimethylacetamide. Cyclic amides are called lactams; they are necessarily secondary or tertiary amides.[5][7]

## Applications

[edit]

See also: polyamide and peptide bond

Amides are pervasive in nature and technology. Proteins and important plastics like nylons, aramids, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD.[8] Low-molecular-weight amides, such as dimethylformamide, are common solvents.

## Structure and bonding

[edit]

Structure of acetamide hydrogen-bonded dimer from X-ray crystallography. Selected distances: C-O: 1.243, C-N, 1.325, N
O, 2.925 Å. Color code: red = O, blue = N, gray = C, white = H.[9]

The lone pair of electrons on the nitrogen atom is delocalized into the Carbonyl group, thus forming a partial double bond between nitrogen and carbon. In fact the O, C and N atoms have molecular orbitals occupied by delocalized electrons, forming a conjugated system. Consequently, the three bonds of the nitrogen in amides is not pyramidal (as in the amines) but planar. This planar restriction prevents rotations about the N linkage and thus has important consequences for the mechanical properties of bulk material of such molecules, and also for the configurational properties of macromolecules built by such bonds. The inability to rotate distinguishes amide groups from ester groups which allow rotation and thus create more flexible bulk material.

The C-C(O)NR2 core of amides is planar. The C=O distance is shorter than the C-N distance by almost 10%. The structure of an amide can be described also as a resonance between two alternative structures: neutral (A) and zwitterionic (B).

It is estimated that for acetamide, structure A makes a 62% contribution to the structure, while structure B makes a 28% contribution (these figures do not sum to 100% because there are additional less-important resonance forms that are not depicted above). There is also a hydrogen bond present between the hydrogen and nitrogen atoms in the active groups.[10] Resonance is largely prevented in the very strained quinuclidone.

In their IR spectra, amides exhibit a moderately intense νCO band near 1650 cm−1. The energy of this band is about 60 cm−1 lower than for the νCO of esters and ketones. This difference reflects the contribution of the zwitterionic resonance structure.

### Basicity

[edit]

Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pKa of about 9.5, the conjugate acid of an amide has a pKa around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of electrons from the amine by the carbonyl. On the other hand, amides are much stronger bases than carboxylic acids, esters, aldehydes, and ketones (their conjugate acids' pKas are between −6 and −10).

The proton of a primary or secondary amide does not dissociate readily; its pKa is usually well above 15. Conversely, under extremely acidic conditions, the carbonyl oxygen can become protonated with a pKa of roughly −1. It is not only because of the positive charge on the nitrogen but also because of the negative charge on the oxygen gained through resonance.

### Hydrogen bonding and solubility

[edit]

Because of the greater electronegativity of oxygen than nitrogen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds also have an important role in the secondary structure of proteins.

The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water.

## Reactions

[edit]

Amides do not readily participate in nucleophilic substitution reactions. Amides are stable to water, and are roughly 100 times more stable towards hydrolysis than esters.[citation needed] Amides can, however, be hydrolyzed to carboxylic acids in the presence of acid or base. The stability of amide bonds has biological implications, since the amino acids that make up proteins are linked with amide bonds. Amide bonds are resistant enough to hydrolysis to maintain protein structure in aqueous environments but are susceptible to catalyzed hydrolysis.[citation needed]

Primary and secondary amides do not react usefully with carbon nucleophiles. Instead, Grignard reagents and organolithiums deprotonate an amide N-H bond. Tertiary amides do not experience this problem, and react with carbon nucleophiles to give ketones; the amide anion (NR2−) is a very strong base and thus a very poor leaving group, so nucleophilic attack only occurs once. When reacted with carbon nucleophiles, N,N-dimethylformamide (DMF) can be used to introduce a formyl group.[11]

Because tertiary amides only react once with organolithiums, they can be used to introduce aldehyde and ketone functionalities. Here, DMF serves as a source of the formyl group in the synthesis of benzaldehyde.

Here, phenyllithium 1 attacks the carbonyl group of DMF 2, giving tetrahedral intermediate 3. Because the dimethylamide anion is a poor leaving group, the intermediate does not collapse and another nucleophilic addition does not occur. Upon acidic workup, the alkoxide is protonated to give 4, then the amine is protonated to give 5. Elimination of a neutral molecule of dimethylamine and loss of a proton give benzaldehyde, 6.

Mechanism for acid-mediated hydrolysis of an amide.[12]

### Hydrolysis

[edit]

Amides hydrolyse in hot alkali as well as in strong acidic conditions. Acidic conditions yield the carboxylic acid and the ammonium ion while basic hydrolysis yield the carboxylate ion and ammonia. The protonation of the initially generated amine under acidic conditions and the deprotonation of the initially generated carboxylic acid under basic conditions render these processes non-catalytic and irreversible. Electrophiles other than protons react with the carbonyl oxygen. This step often precedes hydrolysis, which is catalyzed by both Brønsted acids and Lewis acids. Peptidase enzymes and some synthetic catalysts often operate by attachment of electrophiles to the carbonyl oxygen.

Reaction name | Product | Comment

|
|

Dehydration  | Nitrile  | Reagent: phosphorus pentoxide; benzenesulfonyl chloride; TFAA/py[13]
Hofmann rearrangement | Amine with one fewer carbon atom  | Reagents: bromine and sodium hydroxide
Amide reduction | Amines, aldehydes  | Reagent: lithium aluminium hydride followed by hydrolysis
Vilsmeier–Haack reaction | Aldehyde (via imine)  | POCl3, aromatic substrate, formamide
Bischler–Napieralski reaction | Cyclic aryl imine | POCl3, SOCl2, etc.
Tautomeric chlorination | Imidoyl chloride | Oxophilic halogenating agents, e.g. COCl2 or SOCl2

## Synthesis

[edit]

### From carboxylic acids and related compounds

[edit]

Amides are usually prepared by coupling a carboxylic acid with an amine. The direct reaction generally requires high temperatures to drive off the water:

RCO2H + R'2NH → RCO−2 \+ R'2NH+2
RCO−2 \+ R'2NH+2 → RC(O)NR'2 \+ H2O

Esters are far superior[further explanation needed] substrates relative to carboxylic acids.[14][15][16][better source needed]

Further "activating" both acid chlorides (Schotten-Baumann reaction) and anhydrides (Lumière–Barbier method) react with amines to give amides:

RCO2R" + R'2NH → RC(O)NR'2 \+ R"OH
RCOCl + 2R'2NH → RC(O)NR'2 \+ R'2NH+2Cl−
(RCO)2O + R'2NH → RC(O)NR'2 \+ RCO2H

Peptide synthesis use coupling agents such as HATU, HOBt, or PyBOP.[17]

### From nitriles

[edit]

The hydrolysis of nitriles is conducted on an industrial scale to produce fatty amides.[18] Laboratory procedures are also available.[19]

### Specialty routes

[edit]

Many specialized methods also yield amides.[20] A variety of reagents, e.g. tris(2,2,2-trifluoroethyl) borate have been developed for specialized applications.[21][22]

Specialty Routes to Amides  Reaction name | Substrate | Details

|
|

Beckmann rearrangement | Cyclic ketone  | Reagent: hydroxylamine and acid
Schmidt reaction | Ketones  | Reagent: hydrazoic acid
Willgerodt–Kindler reaction | Aryl alkyl ketones  | Sulfur and morpholine
Passerini reaction | Carboxylic acid, ketone or aldehyde  |
Ugi reaction | Isocyanide, carboxylic acid, ketone, primary amine  |
Bodroux reaction[23][24] | Carboxylic acid, Grignard reagent with an aniline derivative ArNHR'  |
Chapman rearrangement[25][26] | Aryl imino ether | For N,N-diaryl amides. The reaction mechanism is based on a nucleophilic aromatic substitution.[27]
Leuckart amide synthesis[28] | Isocyanate | Reaction of arene with isocyanate catalysed by aluminium trichloride, formation of aromatic amide.
Ritter reaction[29] | Alkenes, alcohols, or other carbonium ion sources  | Secondary amides via an addition reaction between a nitrile and a carbonium ion in the presence of concentrated acids.
Photolytic addition of formamide to olefins[30] | Terminal alkenes | A free radical homologation reaction between a terminal alkene and formamide.
Dehydrogenative coupling[31] | alcohol, amine  | requires ruthenium dehydrogenation catalyst
Transamidation[32][33] | amide  | typically slow

## See also

[edit]

* Amidogen
* Amino radical
* Amidicity
* Imidic acid
* Metal amides

## References

[edit]

1. ^ "Amide definition and meaning - Collins English Dictionary". www.collinsdictionary.com. Retrieved 15 April 2018.
2. ^ "amide". The American Heritage Dictionary of the English Language (5th ed.). HarperCollins.
3. ^ "amide - Definition of amide in English by Oxford Dictionaries". Oxford Dictionaries – English. Archived from the original on 2 April 2015. Retrieved 15 April 2018.
4. ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006-) "amides". doi:10.1351/goldbook.A00266
5. ^ a b c Fletcher, John H. (1974). "Chapter 21: Amides and Imides". Nomenclature of Organic Compounds: Principles and Practice. Vol. 126\. Washington, DC: American Chemical Society. pp. 166–173\. doi:10.1021/ba-1974-0126.ch021. ISBN 9780841201910.
6. ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006-) "Amides". doi:10.1351/goldbook.A00266
7. ^ IUPAC, Chemical Nomenclature and Structure Representation Division (27 October 2004). "Draft Rule P-66.1". Nomenclature of Organic Chemistry (Provisional Recommendations). IUPAC. Full text (PDF) of Draft Rule P-66: Amides, Imides, Hydrazides, Nitriles, Aldehydes, Their Chalcogen Analogues, and Derivatives
8. ^ Boonen, Jente; Bronselaer, Antoon; Nielandt, Joachim; Veryser, Lieselotte; De Tré, Guy; De Spiegeleer, Bart (2012). "Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides" (PDF). Journal of Ethnopharmacology. 142 (3): 563–590\. doi:10.1016/j.jep.2012.05.038. hdl:1854/LU-2133714. PMID 22659196. Archived (PDF) from the original on 9 October 2022.
9. ^ Bats, Jan W.; Haberecht, Monika C.; Wagner, Matthias (2003). "A new refinement of the orthorhombic polymorph of acetamide". Acta Crystallographica Section E. 59 (10): o1483 – o1485. doi:10.1107/S1600536803019494.
10. ^ Kemnitz, Carl R.; Loewen, Mark J. (2007). ""Amide Resonance" Correlates with a Breadth of C−N Rotation Barriers". Journal of the American Chemical Society. 129 (9): 2521–8\. Bibcode:2007JAChS.129.2521K. doi:10.1021/ja0663024. PMID 17295481.
11. ^ Alan R. Katritzky; Meth-Cohn, Otto; Charles Rees, eds. (1995). Comprehensive Organic Functional Group Transformations. Vol. 3 (1st ed.). Oxford: Pergamon Press. p. 90. ISBN 0080423248.
12. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
13. ^ U.S. patent 5,935,953
14. ^ Corson, B. B.; Scott, R. W.; Vose, C. E. (1941). "Cyanoacetamide". Organic Syntheses. 1: 179. doi:10.15227/orgsyn.009.0036.
15. ^ Jacobs, W. A. (1941). "Chloroacetamide". Organic Syntheses. 1: 153. doi:10.15227/orgsyn.007.0016.
16. ^ Kleinberg, J.; Audrieth, L. F. (1955). "Lactamide". Organic Syntheses. 3: 516. doi:10.15227/orgsyn.021.0071.
17. ^ Valeur, Eric; Bradley, Mark (2009). "Amide bond formation: beyond the myth of coupling reagents". Chem. Soc. Rev. 38 (2): 606–631\. doi:10.1039/B701677H. PMID 19169468. S2CID 14950926.
18. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.pub2. ISBN 978-3-527-30673-2.
19. ^ Wenner, Wilhelm (1952). "Phenylacetamide". Organic Syntheses. 32: 92. doi:10.15227/orgsyn.032.0092.
20. ^ De Figueiredo, Renata Marcia; Suppo, Jean-Simon; Campagne, Jean-Marc (2016). "Nonclassical Routes for Amide Bond Formation". Chemical Reviews. 116 (19): 12029–12122\. doi:10.1021/acs.chemrev.6b00237. PMID 27673596.
21. ^ "Tris(2,2,2-trifluoroethyl) borate 97% | Sigma-Aldrich". www.sigmaaldrich.com. Retrieved 22 September 2016.
22. ^ Sabatini, Marco T.; Boulton, Lee T.; Sheppard, Tom D. (1 September 2017). "Borate esters: Simple catalysts for the sustainable synthesis of complex amides". Science Advances. 3 (9): e1701028. Bibcode:2017SciA....3E1028S. doi:10.1126/sciadv.1701028. PMC 5609808. PMID 28948222.
23. ^ Bodroux F. (1905). Bull. Soc. Chim. France. 33: 831.`{{cite journal}}`: CS1 maint: untitled periodical (link)
24. ^ "Bodroux reaction". Institute of Chemistry, Skopje, Macedonia. Archived from the original on 24 September 2015. Retrieved 23 May 2007.
25. ^ Schulenberg, J. W.; Archer, S. (1965). "The Chapman Rearrangement". Org. React. 14: 1–51\. doi:10.1002/0471264180.or014.01. ISBN 978-0471264187.
26. ^ Chapman, Arthur William (1925). "CCLXIX.—Imino-aryl ethers. Part III. The molecular rearrangement of N-phenylbenziminophenyl ether". Journal of the Chemical Society, Transactions. 127: 1992–1998\. doi:10.1039/CT9252701992.
27. ^ March, Jerry (1966). Advanced organic Chemistry, Reactions, mechanisms and structure (3rd ed.). Wiley. ISBN 978-0-471-85472-2.
28. ^ Leuckart, R. (1885). "Ueber einige Reaktionen der aromatischen Cyanate". Berichte der deutschen chemischen Gesellschaft. 18: 873–877\. doi:10.1002/cber.188501801182.
29. ^ Adams, Rodger; Krimen, L.I.; Cota, Donald J. (1969). Organic Reaction Volume 17. London: John Wiley & Sons, Inc. pp. 213–326\. doi:10.1002/0471264180. ISBN 9780471196150.
30. ^ Monson, Richard (1971). Advanced Organic Synthesis: Methods and Techniques (PDF). New York: Academic Press. p. 141\. ISBN 978-0124336803. Archived (PDF) from the original on 9 October 2022.
31. ^ Gunanathan, C.; Ben-David, Y.; Milstein, D. (2007). "Direct Synthesis of Amides from Alcohols and Amines with Liberation of H2". Science. 317 (5839): 790–2\. Bibcode:2007Sci...317..790G. doi:10.1126/science.1145295. PMID 17690291. S2CID 43671648.
32. ^ T. A. Dineen; M. A. Zajac; A. G. Myers (2006). "Efficient Transamidation of Primary Carboxamides by in situ Activation with N,N-Dialkylformamide Dimethyl Acetals". J. Am. Chem. Soc. 128 (50): 16406–16409\. Bibcode:2006JAChS.12816406D. doi:10.1021/ja066728i. PMID 17165798.
33. ^ Emma L. Baker; Michael M. Yamano; Yujing Zhou; Sarah M. Anthony; Neil K. Garg (2016). "A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis". Nature Communications. 7: 11554. Bibcode:2016NatCo...711554B. doi:10.1038/ncomms11554. PMC 4876455. PMID 27199089.

## External links

[edit]

Wikiquote has quotations related to Amide.

* IUPAC Compendium of Chemical Terminology

* v
* t
* e

Nitrogen species

Hydrides|

* NH3
* NH4+
* NH2−
* N3−
* NH2OH
* N2H4
* HN3
* N3−
* NH5 (?)

Organic|

* NR3
* >C=NR
* −CONR2
* −CN
* HCN
* CN−
* (CN)2
* H2NCN
* HOCN
* HNCO
* HNCS
* CH2N2
* -NO
* -NO2

Oxides|

* NO / (NO)2
* N2O3
* HNO2 / NO−
2 / NO+
* NO2 / (NO2)2
* N2O5
* HNO3 / NO−
3 / NO+

* NO3
* HNO / (HON)2 / N2O2−
2 / N2O
* H2NNO2
* HO2NO / ONOO−
* HO2NO2 / O2NOO−
* NO3−

* H4N2O4 / N2O2−

Halides|

* NF
* NF2
* NF3
* NF5 (?)
* NCl3
* NBr3
* NI3
* FN3
* ClN3
* BrN3
* IN3
* NH2F
* N2F2
* NH2Cl
* NHF2
* NHCl2
* NHBr2
* NHI2

Oxidation states|

−3, −2, −1, 0, +1, +2, +3, +4, +5 (a strongly acidic oxide)

* v
* t
* e

Functional groups

Hydrocarbons
(only C and H)|

* Alkyl
* Methyl
* Ethyl
* Propyl
* Cyclopropyl
* Butyl
* Pentyl
* Methylene
* Bridge
* Methine
* Alkene
* Vinyl
* Allyl
* 1-Propenyl
* Crotyl
* Allene
* Cumulene
* Aryl
* Phenyl
* Benzyl
* Alkyne
* Carbene

Only carbon,
hydrogen,
and oxygen
(only C, H and O)|

| R-O-R|

* Acetal
* Alcohol
* Alkoxy
* Methoxy
* Ether
* Enol ether
* Epoxide
* Peroxy
* Hydroperoxy
* Dioxiranes
* Ethylenedioxy
* Methylenedioxy

|

carbonyl|

* Acyl
* Acetyl
* Acryloyl
* Benzoyl
* Aldehyde
* Ketene
* Ketone
* Ynone
* Reductone

carboxy|

* Carboxyl
* Acetoxy
* Anhydride
* Ester
* Orthoester

Only one
element,
not being
carbon,
hydrogen,
or oxygen
(one element,
not C, H or O)|

| Nitrogen|

* Amine
* Enamine
* Ammonium
* Hydrazo
* Nitrene
* Imine
* Oxime
* Hydrazone
* Azo
* Amide
* Imidate
* Amidine
* Carbamate
* Imide
* Nitrile
* Isonitrile
* Cyanate
* Isocyanate
* Nitrate
* Nitrite
* Nitro
* Nitroso
* NONOate
* Triazole
* Tetrazole

|

Silicon|

* Silane
* Hydrosilane
* Chlorosilane
* Silene
* Silanol
* Siloxide
* Siloxane
* Silanone
* Silether
* Silole
* Silatrane
* Silicate

Phosphorus|

* Phosphate
* Phosphodiester
* Phosphonate
* Phosphite
* Phosphonous
* Phosphinate
* Phosphine oxide
* Phosphine
* Phosphonium
* Phosphaalkene
* Phosphaalkyne
* Phosphaallene

Sulfur|

* Thiol
* Thioether
* Sulfonium
* Thia-crown ether
* Persulfide
* Disulfide
* Sulfenic acid
* Thiosulfinate
* Sulfoxide
* Thiosulfonate
* Sulfinic acid
* Sulfone
* Sulfonic acid
* Thioketone
* Thial
* Thioester
* Thionoester
* Thioxanthate
* Xanthate

Boron|

* Boronic acid
* Borinic acid

Selenium|

* Selenol
* Selenonic acid
* Seleninic acid
* Selenenic acid
* Selone
* Selenoether

Tellurium|

* Tellurol
* Telluroketone
* telluroether

Polonium|

* Polonol
* Polonoether

Halo|

* Haloalkane
* Fluoroethyl
* Trifluoromethyl
* Trichloromethyl
* Trifluoromethoxy
* Hypervalent iodine
* Vinyl halide
* Iodide
* Acyl halide
* Chloride
* Perchlorate

Other|

* Isothiocyanate
* Phosphoramides
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate
* Sulfinylamines

See also
chemical classification
chemical nomenclature

inorganic
organic

* v
* t
* e

Topics in organic reactions

* Addition reaction
* Elimination reaction
* Polymerization
* Reagents
* Rearrangement reaction
* Redox reaction
* Regioselectivity
* Stereoselectivity
* Stereospecificity
* Substitution reaction

* A value
* Alpha effect
* Annulene
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* Antiaromaticity
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* Aromaticity
* Baird's rule
* Baker–Nathan effect
* Baldwin's rules
* Bema Hapothle
* Beta-silicon effect
* Bicycloaromaticity
* Bredt's rule
* Bürgi–Dunitz angle
* Catalytic resonance theory
* Charge remote fragmentation
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* Clar's rule
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* Electrophile
* Evelyn effect
* Flippin–Lodge angle
* Free-energy relationship
* Grunwald–Winstein equation
* Hammett acidity function
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* George S. Hammond
* Hammond's postulate
* Homoaromaticity
* Hückel's rule
* Hyperconjugation
* Inductive effect
* Kinetic isotope effect
* LFER solvent coefficients (data page)
* Marcus theory
* Markovnikov's rule
* Möbius aromaticity
* Möbius–Hückel concept
* More O'Ferrall–Jencks plot
* Negative hyperconjugation
* Neighbouring group participation
* 2-Norbornyl cation
* Nucleophile
* Kennedy J. P. Orton
* Passive binding
* Phosphaethynolate
* Polar effect
* Polyfluorene
* Ring strain
* Σ-aromaticity
* Spherical aromaticity
* Spiroaromaticity
* Steric effects
* Superaromaticity
* Swain–Lupton equation
* Taft equation
* Thorpe–Ingold effect
* Vinylogy
* Walsh diagram
* Woodward–Hoffmann rules
* Woodward's rules
* Y-aromaticity
* Yukawa–Tsuno equation
* Zaitsev's rule
* Σ-bishomoaromaticity

List of organic reactions

Carbon-carbon
bond forming
reactions|

* Acetoacetic ester synthesis
* Acyloin condensation
* Aldol condensation
* Aldol reaction
* Alkane metathesis
* Alkyne metathesis
* Alkyne trimerisation
* Alkynylation
* Allan–Robinson reaction
* Arndt–Eistert reaction
* Auwers synthesis
* Aza-Baylis–Hillman reaction
* Barbier reaction
* Barton–Kellogg reaction
* Baylis–Hillman reaction
* Benary reaction
* Bergman cyclization
* Biginelli reaction
* Bingel reaction
* Blaise ketone synthesis
* Blaise reaction
* Blanc chloromethylation
* Bodroux–Chichibabin aldehyde synthesis
* Bouveault aldehyde synthesis
* Bucherer–Bergs reaction
* Buchner ring expansion
* Cadiot–Chodkiewicz coupling
* Carbonyl allylation
* Carbonyl olefin metathesis
* Castro–Stephens coupling
* Chan rearrangement
* Chan–Lam coupling
* Claisen condensation
* Claisen rearrangement
* Claisen-Schmidt condensation
* Combes quinoline synthesis
* Corey–Fuchs reaction
* Corey–House synthesis
* Coupling reaction
* Cross-coupling reaction
* Cross dehydrogenative coupling
* Cross-coupling partner
* Dakin–West reaction
* Darzens reaction
* Diels–Alder reaction
* Doebner reaction
* Wulff–Dötz reaction
* Ene reaction
* Enyne metathesis
* Ethenolysis
* Favorskii reaction
* Ferrier carbocyclization
* Friedel–Crafts reaction
* Fujimoto–Belleau reaction
* Fujiwara–Moritani reaction
* Fukuyama coupling
* Gabriel–Colman rearrangement
* Gattermann reaction
* Glaser coupling
* Grignard reaction
* Grignard reagent
* Hammick reaction
* Heck reaction
* Henry reaction
* Heterogeneous metal catalyzed cross-coupling
* High dilution principle
* Hiyama coupling
* Homologation reaction
* Horner–Wadsworth–Emmons reaction
* Hydrocyanation
* Hydrovinylation
* Hydroxymethylation
* Ivanov reaction
* Johnson–Corey–Chaykovsky reaction
* Julia olefination
* Julia–Kocienski olefination
* Kauffmann olefination
* Knoevenagel condensation
* Knorr pyrrole synthesis
* Kolbe–Schmitt reaction
* Kowalski ester homologation
* Kulinkovich reaction
* Kumada coupling
* Liebeskind–Srogl coupling
* Malonic ester synthesis
* Mannich reaction
* McMurry reaction
* Meerwein arylation
* Methylenation
* Michael reaction
* Minisci reaction
* Mizoroki-Heck vs. Reductive Heck
* Nef isocyanide reaction
* Nef synthesis
* Negishi coupling
* Nierenstein reaction
* Nitro-Mannich reaction
* Nozaki–Hiyama–Kishi reaction
* Olefin conversion technology
* Olefin metathesis
* Palladium–NHC complex
* Passerini reaction
* Peterson olefination
* Pfitzinger reaction
* Piancatelli rearrangement
* Pinacol coupling reaction
* Prins reaction
* Quelet reaction
* Ramberg–Bäcklund reaction
* Rauhut–Currier reaction
* Reformatsky reaction
* Reimer–Tiemann reaction
* Rieche formylation
* Ring-closing metathesis
* Robinson annulation
* Sakurai reaction
* Seyferth–Gilbert homologation
* Shapiro reaction
* Sonogashira coupling
* Stetter reaction
* Stille reaction
* Stollé synthesis
* Stork enamine alkylation
* Suzuki reaction
* Takai olefination
* Thermal rearrangement of aromatic hydrocarbons
* Thorpe reaction
* Ugi reaction
* Ullmann reaction
* Wagner-Jauregg reaction
* Weinreb ketone synthesis
* Wittig reaction
* Wurtz reaction
* Wurtz–Fittig reaction
* Zincke–Suhl reaction

| Homologation reactions|

* Arndt–Eistert reaction
* Hooker reaction
* Kiliani–Fischer synthesis
* Kowalski ester homologation
* Methoxymethylenetriphenylphosphorane
* Seyferth–Gilbert homologation
* Wittig reaction

|

Olefination reactions|

* Bamford–Stevens reaction
* Barton–Kellogg reaction
* Boord olefin synthesis
* Chugaev elimination
* Cope reaction
* Corey–Winter olefin synthesis
* Dehydrohalogenation
* Elimination reaction
* Grieco elimination
* Hofmann elimination
* Horner–Wadsworth–Emmons reaction
* Hydrazone iodination
* Julia olefination
* Julia–Kocienski olefination
* Kauffmann olefination
* McMurry reaction
* Peterson olefination
* Ramberg–Bäcklund reaction
* Shapiro reaction
* Takai olefination
* Wittig reaction

Carbon-heteroatom
bond forming
reactions|

* Azo coupling
* Bartoli indole synthesis
* Boudouard reaction
* Cadogan–Sundberg indole synthesis
* Diazonium compound
* Esterification
* Grignard reagent
* Haloform reaction
* Hegedus indole synthesis
* Hurd–Mori 1,2,3-thiadiazole synthesis
* Kharasch–Sosnovsky reaction
* Knorr pyrrole synthesis
* Leimgruber–Batcho indole synthesis
* Mukaiyama hydration
* Nenitzescu indole synthesis
* Oxymercuration reaction
* Reed reaction
* Schotten–Baumann reaction
* Ullmann condensation
* Williamson ether synthesis
* Yamaguchi esterification

Degradation
reactions|

* Barbier–Wieland degradation
* Bergmann degradation
* Edman degradation
* Emde degradation
* Gallagher–Hollander degradation
* Hofmann rearrangement
* Hooker reaction
* Isosaccharinic acid
* Marker degradation
* Ruff degradation
* Strecker degradation
* Von Braun amide degradation
* Weerman degradation
* Wohl degradation

Organic redox
reactions|

* Acyloin condensation
* Adkins–Peterson reaction
* Akabori amino-acid reaction
* Alcohol oxidation
* Algar–Flynn–Oyamada reaction
* Amide reduction
* Andrussow process
* Angeli–Rimini reaction
* Aromatization
* Autoxidation
* Baeyer–Villiger oxidation
* Barton–McCombie deoxygenation
* Bechamp reduction
* Benkeser reaction
* Bergmann degradation
* Birch reduction
* Bohn–Schmidt reaction
* Bosch reaction
* Bouveault–Blanc reduction
* Boyland–Sims oxidation
* Cannizzaro reaction
* Carbonyl reduction
* Clemmensen reduction
* Collins oxidation
* Corey–Itsuno reduction
* Corey–Kim oxidation
* Corey–Winter olefin synthesis
* Criegee oxidation
* Dakin oxidation
* Davis oxidation
* Deoxygenation
* Dess–Martin oxidation
* DNA oxidation
* Elbs persulfate oxidation
* Emde degradation
* Eschweiler–Clarke reaction
* Étard reaction
* Fischer–Tropsch process
* Fleming–Tamao oxidation
* Fukuyama reduction
* Ganem oxidation
* Glycol cleavage
* Griesbaum coozonolysis
* Grundmann aldehyde synthesis
* Haloform reaction
* Hydrogenation
* Hydrogenolysis
* Hydroxylation
* Jones oxidation
* Kiliani–Fischer synthesis
* Kolbe electrolysis
* Kornblum oxidation
* Kornblum–DeLaMare rearrangement
* Leuckart reaction
* Ley oxidation
* Lindgren oxidation
* Lipid peroxidation
* Lombardo methylenation
* Luche reduction
* Markó–Lam deoxygenation
* McFadyen–Stevens reaction
* Meerwein–Ponndorf–Verley reduction
* Methionine sulfoxide
* Miyaura borylation
* Mozingo reduction
* Noyori asymmetric hydrogenation
* Omega oxidation
* Oppenauer oxidation
* Oxygen rebound mechanism
* Ozonolysis
* Parikh–Doering oxidation
* Pinnick oxidation
* Prévost reaction
* Reduction of nitro compounds
* Reductive amination
* Riley oxidation
* Rosenmund reduction
* Rubottom oxidation
* Sabatier reaction
* Sarett oxidation
* Selenoxide elimination
* Shapiro reaction
* Sharpless asymmetric dihydroxylation
* Epoxidation of allylic alcohols
* Sharpless epoxidation
* Sharpless oxyamination
* Stahl oxidation
* Staudinger reaction
* Stephen aldehyde synthesis
* Swern oxidation
* Transfer hydrogenation
* Wacker process
* Wharton reaction
* Whiting reaction
* Wohl–Aue reaction
* Wolff–Kishner reduction
* Wolffenstein–Böters reaction
* Zinin reaction

Rearrangement
reactions|

* 1,2-rearrangement
* 1,2-Wittig rearrangement
* 2,3-sigmatropic rearrangement
* 2,3-Wittig rearrangement
* Achmatowicz reaction
* Alkyne zipper reaction
* Allen–Millar–Trippett rearrangement
* Allylic rearrangement
* Alpha-ketol rearrangement
* Amadori rearrangement
* Arndt–Eistert reaction
* Aza-Cope rearrangement
* Baker–Venkataraman rearrangement
* Bamberger rearrangement
* Banert cascade
* Beckmann rearrangement
* Benzilic acid rearrangement
* Bergman cyclization
* Bergmann degradation
* Boekelheide reaction
* Brook rearrangement
* Buchner ring expansion
* Carroll rearrangement
* Chan rearrangement
* Claisen rearrangement
* Cope rearrangement
* Corey–Fuchs reaction
* Cornforth rearrangement
* Criegee rearrangement
* Curtius rearrangement
* Demjanov rearrangement
* Di-π-methane rearrangement
* Dimroth rearrangement
* Divinylcyclopropane-cycloheptadiene rearrangement
* Dowd–Beckwith ring-expansion reaction
* Electrocyclic reaction
* Ene reaction
* Enyne metathesis
* Favorskii reaction
* Favorskii rearrangement
* Ferrier carbocyclization
* Ferrier rearrangement
* Fischer–Hepp rearrangement
* Fries rearrangement
* Fritsch–Buttenberg–Wiechell rearrangement
* Gabriel–Colman rearrangement
* Group transfer reaction
* Halogen dance rearrangement
* Hayashi rearrangement
* Hofmann rearrangement
* Hofmann–Martius rearrangement
* Ireland–Claisen rearrangement
* Jacobsen rearrangement
* Kornblum–DeLaMare rearrangement
* Kowalski ester homologation
* Lobry de Bruyn–Van Ekenstein transformation
* Lossen rearrangement
* McFadyen–Stevens reaction
* McLafferty rearrangement
* Meyer–Schuster rearrangement
* Mislow–Evans rearrangement
* Mumm rearrangement
* Myers allene synthesis
* Nazarov cyclization reaction
* Neber rearrangement
* Newman–Kwart rearrangement
* Overman rearrangement
* Oxy-Cope rearrangement
* Pericyclic reaction
* Piancatelli rearrangement
* Pinacol rearrangement
* Pummerer rearrangement
* Ramberg–Bäcklund reaction
* Ring expansion and contraction
* Ring-closing metathesis
* Rupe reaction
* Schmidt reaction
* Semipinacol rearrangement
* Seyferth–Gilbert homologation
* Sigmatropic reaction
* Skattebøl rearrangement
* Smiles rearrangement
* Sommelet–Hauser rearrangement
* Stevens rearrangement
* Stieglitz rearrangement
* Thermal rearrangement of aromatic hydrocarbons
* Tiffeneau–Demjanov rearrangement
* Vinylcyclopropane rearrangement
* Wagner–Meerwein rearrangement
* Wallach rearrangement
* Weerman degradation
* Westphalen–Lettré rearrangement
* Willgerodt rearrangement
* Wolff rearrangement

Ring forming
reactions|

* 1,3-Dipolar cycloaddition
* Annulation
* Azide-alkyne Huisgen cycloaddition
* Baeyer–Emmerling indole synthesis
* Bartoli indole synthesis
* Bergman cyclization
* Biginelli reaction
* Bischler–Möhlau indole synthesis
* Bischler–Napieralski reaction
* Blum–Ittah aziridine synthesis
* Bobbitt reaction
* Bohlmann–Rahtz pyridine synthesis
* Borsche–Drechsel cyclization
* Bucherer carbazole synthesis
* Bucherer–Bergs reaction
* Cadogan–Sundberg indole synthesis
* Camps quinoline synthesis
* Chichibabin pyridine synthesis
* Cook–Heilbron thiazole synthesis
* Cycloaddition
* Darzens reaction
* Davis–Beirut reaction
* De Kimpe aziridine synthesis
* Debus–Radziszewski imidazole synthesis
* Dieckmann condensation
* Diels–Alder reaction
* Feist–Benary synthesis
* Ferrario–Ackermann reaction
* Fiesselmann thiophene synthesis
* Fischer indole synthesis
* Fischer oxazole synthesis
* Friedländer synthesis
* Gewald reaction
* Graham reaction
* Hantzsch pyridine synthesis
* Hegedus indole synthesis
* Hemetsberger indole synthesis
* Hofmann–Löffler reaction
* Hurd–Mori 1,2,3-thiadiazole synthesis
* Iodolactonization
* Isay reaction
* Jacobsen epoxidation
* Johnson–Corey–Chaykovsky reaction
* Knorr pyrrole synthesis
* Knorr quinoline synthesis
* Kröhnke pyridine synthesis
* Kulinkovich reaction
* Larock indole synthesis
* Madelung synthesis
* Nazarov cyclization reaction
* Nenitzescu indole synthesis
* Niementowski quinazoline synthesis
* Niementowski quinoline synthesis
* Paal–Knorr synthesis
* Paternò–Büchi reaction
* Pechmann condensation
* Petrenko-Kritschenko piperidone synthesis
* Pictet–Spengler reaction
* Pomeranz–Fritsch reaction
* Prilezhaev reaction
* Pschorr cyclization
* Reissert indole synthesis
* Ring-closing metathesis
* Robinson annulation
* Sharpless epoxidation
* Simmons–Smith reaction
* Skraup reaction
* Urech hydantoin synthesis
* Van Leusen reaction
* Wenker synthesis

| Cycloaddition|

* 1,3-Dipolar cycloaddition
* 4+4 Photocycloaddition
* (4+3) cycloaddition
* 6+4 Cycloaddition
* Alkyne trimerisation
* Aza-Diels–Alder reaction
* Azide-alkyne Huisgen cycloaddition
* Bradsher cycloaddition
* Cheletropic reaction
* Conia-ene reaction
* Cyclopropanation
* Diazoalkane 1,3-dipolar cycloaddition
* Diels–Alder reaction
* Enone–alkene cycloadditions
* Hexadehydro Diels–Alder reaction
* Intramolecular Diels–Alder cycloaddition
* Inverse electron-demand Diels–Alder reaction
* Ketene cycloaddition
* McCormack reaction
* Metal-centered cycloaddition reactions
* Nitrone-olefin (3+2) cycloaddition
* Oxo-Diels–Alder reaction
* Ozonolysis
* Pauson–Khand reaction
* Povarov reaction
* Prato reaction
* Retro-Diels–Alder reaction
* Staudinger synthesis
* Trimethylenemethane cycloaddition
* Vinylcyclopropane (5+2) cycloaddition
* Wagner-Jauregg reaction

|

Heterocycle forming reactions|

* Algar–Flynn–Oyamada reaction
* Allan–Robinson reaction
* Auwers synthesis
* Bamberger triazine synthesis
* Banert cascade
* Barton–Zard reaction
* Bernthsen acridine synthesis
* Bischler–Napieralski reaction
* Bobbitt reaction
* Boger pyridine synthesis
* Borsche–Drechsel cyclization
* Bucherer carbazole synthesis
* Bucherer–Bergs reaction
* Chichibabin pyridine synthesis
* Cook–Heilbron thiazole synthesis
* Diazoalkane 1,3-dipolar cycloaddition
* Einhorn–Brunner reaction
* Erlenmeyer–Plöchl azlactone and amino-acid synthesis
* Feist–Benary synthesis
* Fischer oxazole synthesis
* Gabriel–Colman rearrangement
* Gewald reaction
* Hantzsch ester
* Hantzsch pyridine synthesis
* Herz reaction
* Knorr pyrrole synthesis
* Kröhnke pyridine synthesis
* Lectka enantioselective beta-lactam synthesis
* Lehmstedt–Tanasescu reaction
* Niementowski quinazoline synthesis
* Nitrone-olefin (3+2) cycloaddition
* Paal–Knorr synthesis
* Pellizzari reaction
* Pictet–Spengler reaction
* Pomeranz–Fritsch reaction
* Prilezhaev reaction
* Robinson–Gabriel synthesis
* Stollé synthesis
* Urech hydantoin synthesis
* Wenker synthesis
* Wohl–Aue reaction

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Other|

* Yale LUX

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