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Aldehyde
In chemistry, an aldehyde /ˈældɪhaɪd/ is an organic compound containing a
functional group with the structure −C(H)=O.[1] The functional group itself (i.e.
without the "R" side chain) is known as an aldehyde or formyl group.
Aldehydes are common and play important roles in the technology and biological
spheres.[2][3]

Contents
Structure and bonding
Physical properties and characterization Aldehyde structure
Applications and occurrence
Naturally occurring aldehydes
Synthesis
Oxidative routes
Specialty methods
Common reactions
Acid-base reactions
Enolization
Reduction
Oxidation
Nucleophilic addition reactions
Oxygen nucleophiles
Nitrogen nucleophiles
Carbon nucleophiles
Bisulfite reaction
More complex reactions
Dialdehydes
Biochemistry
Examples of aldehydes
Examples of dialdehydes
Uses
Nomenclature
IUPAC names for aldehydes
Etymology
See also
References
External links

Structure and bonding

Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and
single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is
often described as being sp2-hybridized. The aldehyde group is somewhat polar. The C=O bond length is about 120-
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122 picometers.[4]

Physical properties and characterization

Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are
more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors.

Aldehydes can be identified by spectroscopic methods. Using IR spectroscopy, they display a strong νCO band near
1700 cm−1. In their 1H NMR spectra, the formyl hydrogen center absorbs near δH 9.5 to 10, which is a distinctive part
of the spectrum. This signal shows the characteristic coupling to any protons on the α carbon with a small coupling
constant typically less than 3.0  Hz. The 13C NMR spectra of aldehydes and ketones gives a suppressed (weak) but
distinctive signal at δC 190 to 205.

Applications and occurrence

Important aldehydes and related compounds. The aldehyde group (or formyl group) is colored red. From the
left: (1) formaldehyde and (2) its trimer 1,3,5-trioxane, (3) acetaldehyde and (4) its enol vinyl alcohol, (5) glucose
(pyranose form as α-d-glucopyranose), (6) the flavorant cinnamaldehyde, (7) the visual pigment retinal, and (8) the
vitamin pyridoxal.

Naturally occurring aldehydes

Traces of many aldehydes are found in essential oils and often contribute to their favorable odours, e.g.
cinnamaldehyde, cilantro, and vanillin. Possibly because of the high reactivity of the formyl group, aldehydes are not
common in several of the natural building blocks: amino acids, nucleic acids, lipids. Most sugars, however, are
derivatives of aldehydes. These aldoses exist as hemiacetals, a sort of masked form of the parent aldehyde. For
example, in aqueous solution only a tiny fraction of glucose exists as the aldehyde.

Synthesis
There are several methods for preparing aldehydes,[2] but the dominant technology is hydroformylation.[5]
Illustrative is the generation of butyraldehyde by hydroformylation of propene:

H2 + CO + CH3CH=CH2 → CH3CH2CH2CHO

Oxidative routes

Aldehydes are commonly generated by alcohol oxidation. In industry, formaldehyde is produced on a large scale by
oxidation of methanol.[6] Oxygen is the reagent of choice, being "green" and cheap. In the laboratory, more
specialized oxidizing agents are used, but chromium(VI) reagents are popular. Oxidation can be achieved by heating
the alcohol with an acidified solution of potassium dichromate. In this case, excess dichromate will further oxidize
the aldehyde to a carboxylic acid, so either the aldehyde is distilled out as it forms (if volatile) or milder reagents such
as PCC are used.[7]

[O] + CH3(CH2)9OH → CH3(CH2)8CHO + H2O

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Oxidation of primary alcohols to form aldehydes can be achieved under milder, chromium-free conditions by
employing methods or reagents such as IBX acid, Dess–Martin periodinane, Swern oxidation, TEMPO, or the
Oppenauer oxidation.

Another oxidation route significant in industry is the Wacker process, whereby ethylene is oxidized to acetaldehyde
in the presence of copper and palladium catalysts (acetaldehyde is also produced on a large scale by the hydration of
acetylene).

On the laboratory scale, α-hydroxy acids are used as precursors to prepare aldehydes via oxidative cleavage.[8][9]

Specialty methods
Reaction name Substrate Comment
Ozonolysis Alkenes Ozonolysis of non-fully-substituted alkenes yield aldehydes upon a
reductive work-up.
Organic reduction Reduction of an ester with diisobutylaluminium hydride (DIBAL-H) or
Esters
sodium aluminium hydride.
Rosenmund reaction Acyl chlorides Acyl chlorides selectively reduced to aldehydes. Lithium tri-t-
butoxyaluminium hydride (LiAlH(OtBu)3) is an effective reagent.

Wittig reaction Ketones A modified Wittig reaction using methoxymethylenetriphenylphosphine

as a reagent.
Formylation reactions Nucleophilic
Various reactions, for example the Vilsmeier-Haack reaction.
arenes
Nef reaction Nitro compounds The acid hydrolysis of a primary nitro compound to form an aldehyde.
Kornblum oxidation Haloalkanes The oxidation of primary halide with dimethyl sulfoxide to form an
aldehyde.
Zincke reaction Pyridines Zincke aldehydes formed in a reaction variation.
Stephen aldehyde synthesis Nitriles Hydrolysis of an iminium salt generated by tin(II) chloride and HCl to
form an aldehyde.
Geminal halide hydrolysis Geminal dihalides Hydrolysis of primary geminal dihalides to yield aldehydes.
Meyers synthesis Oxazines Hemiaminal oxazine hydrolysis with water and oxalic acid to yield an
aldehyde.
Hofmann rearrangement unsaturated or α-
Aldehydes via the hydrolysis of an intermediate carbamate.
variation[10][11] hydroxy amides

McFadyen-Stevens reaction Hydrazides Base-catalyzed thermal decomposition of acylsulfonylhydrazides.

Biotransformation Alkenes Lyophilized cell cultures of Trametes hirsuta in the presence of
oxygen.[12]

Common reactions
Aldehydes participate in many reactions.[2] From the industrial perspective, important reactions are (a)
condensations, e.g., to prepare plasticizers and polyols, and (b) reduction to produce alcohols, especially "oxo-
alcohols". From the biological perspective, the key reactions involve addition of nucleophiles to the formyl carbon in
the formation of imines (oxidative deamination) and hemiacetals (structures of aldose sugars).[2]

Acid-base reactions

Because of resonance stabilization of the conjugate base, an α-hydrogen in an aldehyde is weakly acidic, with a pKa
near 17. This acidification is attributed to (i) the electron-withdrawing quality of the formyl center and (ii) the fact
that the conjugate base, an enolate anion, delocalizes its negative charge. The formyl proton itself does not readily
undergo deprotonation.

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Enolization

Aldehydes (except those without an alpha carbon, or without protons on the alpha carbon, such as formaldehyde and
benzaldehyde) can exist in either the keto or the enol tautomer. Keto–enol tautomerism is catalyzed by either acid or
base. Usually the enol is the minority tautomer, but it is more reactive. The enolization typically reverses several
times per second.[13]

Reduction

The formyl group can be readily reduced to a primary alcohol (−CH2OH). Typically this conversion is accomplished
by catalytic hydrogenation either directly or by transfer hydrogenation. Stoichiometric reductions are also popular, as
can be effected with sodium borohydride.

Oxidation

The formyl group readily oxidizes to the corresponding carboxyl group (−COOH). The preferred oxidant in industry
is oxygen or air. In the laboratory, popular oxidizing agents include potassium permanganate, nitric acid,
chromium(VI) oxide, and chromic acid. The combination of manganese dioxide, cyanide, acetic acid and methanol
will convert the aldehyde to a methyl ester.[14]

Another oxidation reaction is the basis of the silver-mirror test. In this test, an aldehyde is treated with Tollens'
reagent, which is prepared by adding a drop of sodium hydroxide solution into silver nitrate solution to give a
precipitate of silver(I) oxide, and then adding just enough dilute ammonia solution to redissolve the precipitate in
aqueous ammonia to produce [Ag(NH3)2]+ complex. This reagent converts aldehydes to carboxylic acids without
attacking carbon–carbon double bonds. The name silver-mirror test arises because this reaction produces a
precipitate of silver, whose presence can be used to test for the presence of an aldehyde.

A further oxidation reaction involves Fehling's reagent as a test. The Cu2+ complex ions are reduced to a red-brick-
coloured Cu2O precipitate.

If the aldehyde cannot form an enolate (e.g., benzaldehyde), addition of strong base induces the Cannizzaro reaction.
This reaction results in disproportionation, producing a mixture of alcohol and carboxylic acid.

Nucleophilic addition reactions

Nucleophiles add readily to the carbonyl group. In the product, the carbonyl carbon becomes sp3-hybridized, being
bonded to the nucleophile, and the oxygen center becomes protonated:

RCHO + Nu− → RCH(Nu)O−

RCH(Nu)O− + H+ → RCH(Nu)OH

In many cases, a water molecule is removed after the addition takes place; in this case, the reaction is classed as an
addition–elimination or addition–condensation reaction. There are many variations of nucleophilic addition
reactions.

Oxygen nucleophiles

In the acetalisation reaction, under acidic or basic conditions, an alcohol adds to the carbonyl group and a proton is
transferred to form a hemiacetal. Under acidic conditions, the hemiacetal and the alcohol can further react to form
an acetal and water. Simple hemiacetals are usually unstable, although cyclic ones such as glucose can be stable.
Acetals are stable, but revert to the aldehyde in the presence of acid. Aldehydes can react with water to form hydrates,
R−CH(OH)2. These diols are stable when strong electron withdrawing groups are present, as in chloral hydrate. The
mechanism of formation is identical to hemiacetal formation.

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Nitrogen nucleophiles

In alkylimino-de-oxo-bisubstitution, a primary or secondary amine adds to the carbonyl group and a proton is
transferred from the nitrogen to the oxygen atom to create a carbinolamine. In the case of a primary amine, a water
molecule can be eliminated from the carbinolamine intermediate to yield an imine or its trimer, a hexahydrotriazine
This reaction is catalyzed by acid. Hydroxylamine (NH2OH) can also add to the carbonyl group. After the elimination
of water, this results in an oxime. An ammonia derivative of the form H2NNR2 such as hydrazine (H2NNH2) or 2,4-
dinitrophenylhydrazine can also be the nucleophile and after the elimination of water, resulting in the formation of a
hydrazone, which are usually orange crystalline solids. This reaction forms the basis of a test for aldehydes and
ketones.[15]

Carbon nucleophiles

The cyano group in HCN can add to the carbonyl group to form cyanohydrins, R−CH(OH)CN. In this reaction the
CN− ion is the nucleophile that attacks the partially positive carbon atom of the carbonyl group. The mechanism
involves a pair of electrons from the carbonyl-group double bond transferring to the oxygen atom, leaving it single-
bonded to carbon and giving the oxygen atom a negative charge. This intermediate ion rapidly reacts with H+, such
as from the HCN molecule, to form the alcohol group of the cyanohydrin.

Organometallic compounds, such as organolithium reagents, Grignard reagents, or acetylides, undergo nucleophilic
addition reactions, yielding a substituted alcohol group. Related reactions include organostannane additions, Barbier
reactions, and the Nozaki–Hiyama–Kishi reaction.

In the aldol reaction, the metal enolates of ketones, esters, amides, and carboxylic acids add to aldehydes to form β-
hydroxycarbonyl compounds (aldols). Acid or base-catalyzed dehydration then leads to α,β-unsaturated carbonyl
compounds. The combination of these two steps is known as the aldol condensation.

The Prins reaction occurs when a nucleophilic alkene or alkyne reacts with an aldehyde as electrophile. The product
of the Prins reaction varies with reaction conditions and substrates employed.

Bisulfite reaction

Aldehydes characteristically form "addition compounds" with sodium bisulfite:

−
−

RCHO + HSO3 → RCH(OH)SO3

This reaction is used as a test for aldehydes.[15]

More complex reactions

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Reaction
Product Comment
name
Wolff–Kishner Alkane If an aldehyde is converted to a simple hydrazone (RCH=NHNH2) and this is heated with a base
reduction such as KOH, the terminal carbon is fully reduced to a methyl group. The Wolff–Kishner reaction
may be performed as a one-pot reaction, giving the overall conversion RCH=O → RCH3.

Pinacol
coupling Diol With reducing agents such as magnesium
reaction
Wittig reaction Alkene Reagent: an ylide
Takai reaction Alkene Diorganochromium reagent
Corey–Fuchs Alkyne
Phosphine-dibromomethylene reagent
reactions
Ohira– Alkyne
Bestmann Reagent: dimethyl (diazomethyl)phosphonate
reaction
Johnson– Epoxide
Corey–
Reagent: a sulfonium ylide
Chaykovsky
reaction
Oxo-Diels– Pyran Aldehydes can, typically in the presence of suitable catalysts, serve as partners in cycloaddition
Alder reaction reactions. The aldehyde serves as the dienophile component, giving a pyran or related compound.
Hydroacylation Ketone In hydroacylation an aldehyde is added over an unsaturated bond to form a ketone.
decarbonylation Alkane Catalysed by transition metals

Dialdehydes
A dialdehyde is an organic chemical compound with two aldehyde groups. The nomenclature of dialdehydes have
the ending -dial or sometimes -dialdehyde. Short aliphatic dialdehydes are sometimes named after the diacid from
which they can be derived. An example is butanedial, which is also called succinaldehyde (from succinic acid).

Biochemistry
Some aldehydes are substrates for aldehyde dehydrogenase enzymes which metabolize aldehydes in the body. There
are toxicities associated with some aldehydes that are related to neurodegenerative disease, heart disease, and some
types of cancer.[16]

Examples of aldehydes
Formaldehyde (methanal)
Acetaldehyde (ethanal)
Propionaldehyde (propanal)
Butyraldehyde (butanal)
Isovaleraldehyde
Benzaldehyde (phenylmethanal)
Cinnamaldehyde
Vanillin
Tolualdehyde
Furfural
Retinaldehyde
Glycolaldehyde

Examples of dialdehydes
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Glyoxal
Malondialdehyde
Succindialdehyde
Glutaraldehyde
Phthalaldehyde

Uses
Of all aldehydes, formaldehyde is produced on the largest scale, about 6 000 000 tons per year. It is mainly used in
the production of resins when combined with urea, melamine, and phenol (e.g., Bakelite). It is a precursor to
methylene diphenyl diisocyanate ("MDI"), a precursor to polyurethanes.[6] The second main aldehyde is
butyraldehyde, of which about 2 500 000  tons per year are prepared by hydroformylation. It is the principal
precursor to 2-ethylhexanol, which is used as a plasticizer.[17] Acetaldehyde once was a dominating product, but
production levels have declined to less than 1 000 000 tons per year because it mainly served as a precursor to acetic
acid, which is now prepared by carbonylation of methanol. Many other aldehydes find commercial applications, often
as precursors to alcohols, the so-called oxo alcohols, which are used in detergents. Some aldehydes are produced only
on a small scale (less than 1000 tons per year) and are used as ingredients in flavours and perfumes such as Chanel
No. 5. These include cinnamaldehyde and its derivatives, citral, and lilial.

Nomenclature

IUPAC names for aldehydes

The common names for aldehydes do not strictly follow official guidelines, such as those recommended by IUPAC,
but these rules are useful. IUPAC prescribes the following nomenclature for aldehydes:[18][19][20]

1. Acyclic aliphatic aldehydes are named as derivatives of the longest carbon chain containing the aldehyde group.
Thus, HCHO is named as a derivative of methane, and CH3CH2CH2CHO is named as a derivative of butane.
The name is formed by changing the suffix -e of the parent alkane to -al, so that HCHO is named methanal, and
CH3CH2CH2CHO is named butanal.
2. In other cases, such as when a -CHO group is attached to a ring, the suffix -carbaldehyde may be used. Thus,
C6H11CHO is known as cyclohexanecarbaldehyde. If the presence of another functional group demands the use
of a suffix, the aldehyde group is named with the prefix formyl-. This prefix is preferred to methanoyl-.
3. If the compound is a natural product or a carboxylic acid, the prefix oxo- may be used to indicate which carbon
atom is part of the aldehyde group; for example, CHOCH2COOH is named 3-oxopropanoic acid.
4. If replacing the aldehyde group with a carboxyl group (−COOH) would yield a carboxylic acid with a trivial name,
the aldehyde may be named by replacing the suffix -ic acid or -oic acid in this trivial name by -aldehyde.

Etymology

The word aldehyde was coined by Justus von Liebig as a contraction of the Latin alcohol dehydrogenatus
(dehydrogenated alcohol).[21][22] In the past, aldehydes were sometimes named after the corresponding alcohols, for
example, vinous aldehyde for acetaldehyde. (Vinous is from Latin vinum "wine", the traditional source of ethanol,
cognate with vinyl.)

The term formyl group is derived from the Latin word formica "ant". This word can be recognized in the simplest
aldehyde, formaldehyde, and in the simplest carboxylic acid, formic acid.

See also
Enol
Pseudoacid

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References
1. IUPAC Gold Book, aldehydes (http://goldbook.iupac.org/A00208.html).
2. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (htt
ps://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover) (6th ed.), New York: Wiley-Interscience,
ISBN 978-0-471-72091-1
3. Saul Patai, ed. (1966). The Carbonyl Group. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons.
doi:10.1002/9780470771051 (https://doi.org/10.1002%2F9780470771051). ISBN 9780470771051.Jacob
Zabicky, ed. (1970). The Carbonyl Group. PATAI'S Chemistry of Functional Groups. Vol. 2. John Wiley & Sons.
doi:10.1002/9780470771228 (https://doi.org/10.1002%2F9780470771228). ISBN 9780470771228.
4. G. Berthier, J. Serre (1966). "General and Theoretical Aspects of the Carbonyl Goup". In Saul Patai (ed.). The
Carbonyl Group. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons. p. 1-77.
doi:10.1002/9780470771051.ch1 (https://doi.org/10.1002%2F9780470771051.ch1).
5. Bertleff, W.; Roeper, M. and Sava, X. (2003) "Carbonylation" in Ullmann’s Encyclopedia of Industrial Chemistry,
Wiley-VCH: Weinheim. doi:10.1002/14356007.a05_217.pub2 (https://doi.org/10.1002%2F14356007.a05_217.pu
b2)
6. Reuss, G.; Disteldorf, W.; Gamer, A. O. and Hilt, A. (2005) "Formaldehyde" in Ullmann's Encyclopedia of
Industrial Chemistry. Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_619 (https://doi.org/10.1002%2F143560
07.a11_619).
7. Ratcliffe, R. W. (1988). "Oxidation with the Chromium Trioxide-Pyridine Complex Prepared in situ: 1-Decanal" (htt
p://www.orgsyn.org/demo.aspx?prep=cv6p0373). Organic Syntheses.; Collective Volume, vol. 6, p. 373
8. Ōeda, Haruomi (1934). "Oxidation of some α-hydroxy-acids with lead tetraacetate" (https://doi.org/10.1246%2Fbc
sj.9.8). Bulletin of the Chemical Society of Japan. 9 (1): 8–14. doi:10.1246/bcsj.9.8 (https://doi.org/10.1246%2Fbc
sj.9.8).
9. Nwaukwa, Stephen; Keehn, Philip (1982). "Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-
hydroxy- and α-keto acids with calcium hypochlorite [Ca(OCl)2]". Tetrahedron Letters. 23 (31): 3135–3138.
doi:10.1016/S0040-4039(00)88578-0 (https://doi.org/10.1016%2FS0040-4039%2800%2988578-0).
10. Weerman, R.A. (1913). "Einwirkung von Natriumhypochlorit auf Amide ungesättigter Säuren" (https://zenodo.org/
record/1427615). Justus Liebigs Annalen der Chemie. 401 (1): 1–20. doi:10.1002/jlac.19134010102 (https://doi.o
rg/10.1002%2Fjlac.19134010102).
11. Everett, Wallis; Lane, John (1946). The Hofmann Reaction. Organic Reactions. Vol. 3. pp. 267–306.
doi:10.1002/0471264180.or003.07 (https://doi.org/10.1002%2F0471264180.or003.07). ISBN 9780471005285.
12. Sutton, Peter; Whittall, John (2012). Practical Methods for Biocatalysis and Biotransformations 2 (https://books.go
ogle.com/books?id=WlODZ-WX8vIC&q=9781119991397). Chichester, West Sussex: John Wiley & Sons, Ltd.
pp. 199–202. ISBN 9781119991397.
13. aldehyde Tautomerism|Britannica[1] (https://www.britannica.com/science/aldehyde/Tautomerism)
14. Corey, Elias J.; Gilman, Norman W.; Ganem, B. E. (1968). "New methods for the oxidation of aldehydes to
carboxylic acids and esters". J. Am. Chem. Soc. 90 (20): 5616–5617. doi:10.1021/ja01022a059 (https://doi.org/1
0.1021%2Fja01022a059).
15. Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C. (1997). The Systematic Identification of
Organic Compounds. John Wiley & Sons. ISBN 978-0-471-59748-3.
16. Chen, Che-Hong; Ferreira, Julio Cesar Batista; Gross, Eric R.; Rosen, Daria Mochly (1 January 2014). "Targeting
Aldehyde Dehydrogenase 2: New Therapeutic Opportunities" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC392
9114). Physiological Reviews. 94 (1): 1–34. doi:10.1152/physrev.00017.2013 (https://doi.org/10.1152%2Fphysrev.
00017.2013). PMC 3929114 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929114). PMID 24382882 (https://p
ubmed.ncbi.nlm.nih.gov/24382882).
17. Kohlpaintner, C.; Schulte, M.; Falbe, J.; Lappe, P. and Weber, J. (2008) "Aldehydes, Aliphatic" in Ullmann's
Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_321.pub2 (https://doi.or
g/10.1002%2F14356007.a01_321.pub2).
18. Short Summary of IUPAC Nomenclature of Organic Compounds (http://www.uwc.edu/dept/chemistry/helpful_file
s/nomenclature.pdf) Archived (https://web.archive.org/web/20060901144219/http://www.uwc.edu/dept/chemistry/
helpful_files/nomenclature.pdf) 2006-09-01 at the Wayback Machine, web page, University of Wisconsin
Colleges, accessed on line August 4, 2007.

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19. §R-5.6.1, Aldehydes, thioaldehydes, and their analogues, A Guide to IUPAC Nomenclature of Organic
Compounds: recommendations 1993 (http://www.acdlabs.com/iupac/nomenclature/93/r93_449.htm), IUPAC,
Commission on Nomenclature of Organic Chemistry, Blackwell Scientific, 1993.
20. §R-5.7.1, Carboxylic acids, A Guide to IUPAC Nomenclature of Organic Compounds: recommendations 1993 (htt
p://www.acdlabs.com/iupac/nomenclature/93/r93_480.htm), IUPAC, Commission on Nomenclature of Organic
Chemistry, Blackwell Scientific, 1993.
21. Liebig, J. (1835) "Sur les produits de l'oxidation de l'alcool" (https://books.google.com/books?id=85c5AAAAcAAJ
&pg=PA289#v=onepage&q&f=false) (On the products of the oxidation of alcohol), Annales de Chimie et de
Physique, 59 : 289–327. From page 290: "Je le décrirai dans ce mémoire sous le nom d'aldehyde ; ce nom est
formé de alcool dehydrogenatus." (I will describe it in this memoir by the name of aldehyde; this name is formed
from alcohol dehydrogenatus.)
22. Crosland, Maurice P. (2004), Historical Studies in the Language of Chemistry (https://books.google.com/books?id
=kwQQaltqByAC&q=alcohol+dehydrogenatus&pg=PA297), Courier Dover Publications, ISBN 9780486438023.

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