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'''Acetaldehyde,''' sometimes known as '''ethanal,''' is an [[organic compound|organic chemical compound]] with the [[chemical formula|formula]] [[Carbon|C]][[Hydrogen|H]]<sub>3</sub>CH[[Oxygen|O]] (or MeCHO). It is a flammable liquid with a fruity smell. It occurs naturally in ripe [[fruit]], [[coffee]], and fresh [[bread]] and is produced by [[plant]]s as part of their normal [[metabolism]]. It is perhaps best known as the chemical that causes "[[hangovers]]." In the chemical industry, acetaldehyde is used as an intermediate in the production of [[acetic acid]], certain [[ester]]s, and a number of other chemicals. | '''Acetaldehyde,''' sometimes known as '''ethanal,''' is an [[organic compound|organic chemical compound]] with the [[chemical formula|formula]] [[Carbon|C]][[Hydrogen|H]]<sub>3</sub>CH[[Oxygen|O]] (or MeCHO). It is a flammable liquid with a fruity smell. It occurs naturally in ripe [[fruit]], [[coffee]], and fresh [[bread]] and is produced by [[plant]]s as part of their normal [[metabolism]]. It is perhaps best known as the chemical that causes "[[hangovers]]." In the chemical industry, acetaldehyde is used as an intermediate in the production of [[acetic acid]], certain [[ester]]s, and a number of other chemicals. | ||
| − | + | {{toc}} | |
==Ethenol== | ==Ethenol== | ||
| − | Traces of acetaldehyde exist in the [[enol]] form, [[ethenol]], with K<sub>eq</sub> = 6 x 10<sup>-5</sup>.<ref>March | + | Traces of acetaldehyde exist in the [[enol]] form, [[ethenol]], with K<sub>eq</sub> = 6 x 10<sup>-5</sup>.<ref>Jerry March, ''Advanced Organic Chemistry: Reactions, Mechanisms, and Structure'' (Wiley; 4 edition, 1992, ISBN 978-0471581482).</ref> Ethenol has been detected in the interstellar medium. |
==Applications in Organic Synthesis== | ==Applications in Organic Synthesis== | ||
| − | Acetaldehyde is a common 2-carbon building block in [[organic synthesis]].<ref> | + | Acetaldehyde is a common 2-carbon building block in [[organic synthesis]].<ref>Leo A. Paquette, David Crich, Philip L. Fuchs, and Gary A. Molander (eds.), ''Encyclopedia of Reagents for Organic Synthesis'' (Wiley, 2009, ISBN 978-0470017548). </ref> Because of its small size and its availability as the anhydrous monomer (unlike formaldehyde), it is a common electrophile. With respect to its condensation reactions, acetaldehyde is [[prochiral]]. It is mainly used as a source of the CH<sub>3</sub>C<sup>+</sup>H(OH) [[synthon]] in [[aldol condensation|aldol]] and related condensation reactions.<ref>Behrens, C., and Paquette, L.A., “N-Benzyl-2,3-Azetidinedione.” ''Organic Syntheses, Collected Volume 10.'' 2004, 41. </ref> Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives.<ref>Walter, L.A., “1-(α-Pyridyl)-2-Propanol” ''Organic Syntheses, Collected Volume 3.'' 1955, 757. </ref> In one of the more spectacular condensation reactions, three equivalents of [[formaldehyde]] add to MeCHO to give [[pentaerythritol]], C(CH<sub>2</sub>OH)<sub>4</sub>.<ref>Schurink, H. B. J., “Pentaerythritol.” ''Organic Syntheses, Collected Volume 1.'' 1941, 425. </ref> |
| − | In a [[Strecker amino acid synthesis|Strecker reaction]], acetaldehyde condenses with [[cyanide]] and [[ammonia]] to give, after [[hydrolysis]], the [[amino acid]] alanine.<ref>Kendall, E.C., and McKenzie, B.F., “''dl''-Alanine.” ''Organic Syntheses, Collected Volume 1.'' 1941 | + | In a [[Strecker amino acid synthesis|Strecker reaction]], acetaldehyde condenses with [[cyanide]] and [[ammonia]] to give, after [[hydrolysis]], the [[amino acid]] alanine.<ref>Kendall, E.C., and McKenzie, B.F., “''dl''-Alanine.” ''Organic Syntheses, Collected Volume 1.'' 1941, 21. </ref> Acetaldehyde can condense with amines to yield imines, such as the condensation with cyclohexylamine to give N-ethylidenecyclohexylamine. These imines can be used to direct subsequent reactions like an aldol condensation.<ref>Georg Wittig and A. Hesse, “Directed Aldol Condensations: β-Phenylcinnamaldehyde” ''Organic Syntheses, Collected Volume 6.'' 1988, 901. </ref> |
| − | It is also an important building block for the synthesis of [[heterocyclic compounds]]. A remarkable example is its conversion upon treatment with [[ammonia]] to 5-ethyl-2-methylpyridine ("aldehyde-collidine”).<ref> | + | It is also an important building block for the synthesis of [[heterocyclic compounds]]. A remarkable example is its conversion upon treatment with [[ammonia]] to 5-ethyl-2-methylpyridine ("aldehyde-collidine”).<ref>R.L. Frank, F.J. Pilgrim, and E.F. Riener, “5-Ethyl-2-Methylpyridine” ''Organic Syntheses, Collected Volume 4.'' 1963, 451. </ref> |
===Acetal Derivatives=== | ===Acetal Derivatives=== | ||
| − | |||
Three molecules of acetaldehyde condense to form “[[paraldehyde]],” a cyclic trimer containing C-O single bonds; four condense to form the cyclic molecule called [[metaldehyde]]. | Three molecules of acetaldehyde condense to form “[[paraldehyde]],” a cyclic trimer containing C-O single bonds; four condense to form the cyclic molecule called [[metaldehyde]]. | ||
| − | Acetaldehyde forms a stable [[acetal]] upon reaction with [[ethanol]] under conditions that favor dehydration. The product, CH<sub>3</sub>CH(OCH<sub>2</sub>CH<sub>3</sub>)<sub>2</sub>, is in fact called "acetal," although acetal is used more widely to describe other compounds with the formula RCH(OR')<sub>2</sub>.<ref> | + | Acetaldehyde forms a stable [[acetal]] upon reaction with [[ethanol]] under conditions that favor dehydration. The product, CH<sub>3</sub>CH(OCH<sub>2</sub>CH<sub>3</sub>)<sub>2</sub>, is in fact called "acetal," although acetal is used more widely to describe other compounds with the formula RCH(OR')<sub>2</sub>.<ref>H. Adkins and B.H. Nissen, “Acetal” ''Organic Syntheses, Collected Volume 1.'' 1941, 1. </ref> |
==Biological Aspects== | ==Biological Aspects== | ||
| − | |||
In the [[liver]], the [[enzyme]] [[alcohol dehydrogenase]] converts ethanol into acetaldehyde, which is then further converted into harmless [[acetic acid]] by [[acetaldehyde dehydrogenase]]. The last steps of alcoholic [[fermentation (food)|fermentation]] in [[bacterium|bacteria]], [[plant]]s, and [[yeast]] involve the conversion of [[pyruvate]] into acetaldehyde by the enzyme [[pyruvate decarboxylase]], followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction. | In the [[liver]], the [[enzyme]] [[alcohol dehydrogenase]] converts ethanol into acetaldehyde, which is then further converted into harmless [[acetic acid]] by [[acetaldehyde dehydrogenase]]. The last steps of alcoholic [[fermentation (food)|fermentation]] in [[bacterium|bacteria]], [[plant]]s, and [[yeast]] involve the conversion of [[pyruvate]] into acetaldehyde by the enzyme [[pyruvate decarboxylase]], followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction. | ||
===Acetaldehyde and Hangovers=== | ===Acetaldehyde and Hangovers=== | ||
| − | Most people of [[East Asia]]n descent have a [[mutation]] in their [[alcohol dehydrogenase]] [[gene]] that makes this enzyme unusually effective at converting ethanol to acetaldehyde, and about half of such people also have a form of [[acetaldehyde dehydrogenase]] which is less effective at converting acetaldehyde to acetic acid. <ref> | + | Most people of [[East Asia]]n descent have a [[mutation]] in their [[alcohol dehydrogenase]] [[gene]] that makes this enzyme unusually effective at converting ethanol to acetaldehyde, and about half of such people also have a form of [[acetaldehyde dehydrogenase]] which is less effective at converting acetaldehyde to acetic acid. <ref> Q. Xiao, H. Weiner, and D.W. Crabb, [https://www.jci.org/articles/view/119007 “The Mutation in the Mitochondrial Aldehyde Dehydrogenase (ALDH2) Gene Responsible for Alcohol-Induced Flushing Increases Turnover of the Enzyme Tetramers in a Dominant Fashion.”] ''J. Clin. Invest.'' 1996, 2027-2032. Retrieved April 3, 2018.</ref> This combination causes them to suffer from the [[alcohol flush reaction]], in which acetaldehyde accumulates after drinking, leading to severe and immediate hangover symptoms. These people are therefore less likely to become [[alcoholic]]s. The drug [[Antabuse]] ([[disulfiram]]) also prevents the oxidation of acetaldehyde to acetic acid, with the same unpleasant effects for drinkers. It has been used in the treatment of alcoholism. |
==Other Occurrences== | ==Other Occurrences== | ||
| − | + | Acetaldehyde is an [[air pollution|air pollutant]] resulting from combustion, such as automotive exhaust and [[tobacco smoking|tobacco smoke]], contributing to the addictive properties of tobacco. | |
| − | Acetaldehyde is an [[air pollution|air pollutant]] resulting from combustion, such as automotive exhaust and [[tobacco smoking|tobacco smoke]], contributing to the addictive properties of tobacco. | ||
==Safety== | ==Safety== | ||
| − | + | Acetaldehyde is a toxin, an irritant, and a probable [[carcinogen]]. | |
| − | Acetaldehyde is a toxin, an irritant, and a probable [[carcinogen]]. | ||
==See Also== | ==See Also== | ||
| − | |||
* [[Aldehyde]] | * [[Aldehyde]] | ||
* [[Acetic acid]] | * [[Acetic acid]] | ||
| Line 148: | Line 143: | ||
== Notes == | == Notes == | ||
| − | |||
<references/> | <references/> | ||
==References== | ==References== | ||
| − | + | * March, Jerry. ''Advanced Organic Chemistry: Reactions, Mechanisms, and Structure''. Wiley; 4 edition, 1992. ISBN 978-0471581482 | |
* McMurry, John. ''Organic Chemistry.'' 6th ed. Belmont, CA: Brooks/Cole. 2004. ISBN 0534420052 | * McMurry, John. ''Organic Chemistry.'' 6th ed. Belmont, CA: Brooks/Cole. 2004. ISBN 0534420052 | ||
| − | * Morrison, Robert T., and Boyd, Robert N. ''Organic Chemistry.'' 6th ed. Englewood Cliffs, NJ: Prentice Hall. 1992. ISBN | + | * Morrison, Robert T., and Boyd, Robert N. ''Organic Chemistry.'' 6th ed. Englewood Cliffs, NJ: Prentice Hall. 1992. ISBN 0136436692 |
| + | * Paquette, Leo A., David Crich, Philip L. Fuchs, and Gary A. Molander (eds.). ''Encyclopedia of Reagents for Organic Synthesis''. Wiley, 2009. ISBN 978-0470017548 | ||
* Solomons, T.W. Graham, and Fryhle, Craig B. ''Organic Chemistry.'' 8th ed. Hoboken, NJ: John Wiley. 2004. ISBN 0471417998 | * Solomons, T.W. Graham, and Fryhle, Craig B. ''Organic Chemistry.'' 8th ed. Hoboken, NJ: John Wiley. 2004. ISBN 0471417998 | ||
== External Links == | == External Links == | ||
| − | All links retrieved | + | All links retrieved June 14, 2023. |
| − | |||
| − | |||
* National Institute for Occupational Safety and Health. [http://www.cdc.gov/niosh/npg/npgd0001.html NIOSH Pocket Guide to Chemical Hazards.] | * National Institute for Occupational Safety and Health. [http://www.cdc.gov/niosh/npg/npgd0001.html NIOSH Pocket Guide to Chemical Hazards.] | ||
| − | + | ||
Latest revision as of 07:33, 14 June 2023
| Acetaldehyde | |
|---|---|
 
| |
| Common name | acetaldehyde |
| IUPAC name | acetaldehyde |
| Systematic name | ethanal |
| Chemical formula | C2H4O |
| SMILES | CC=O |
| Molecular mass | 44.05 g mol−1 |
| Appearance | Colorless liquid Pungent, fruity odor |
| CAS number | [75-07-0] |
| Properties | |
| Density | 0.788 g cm−3 |
| Solubility in water | soluble in all proportions |
| Melting point | −123.5 °C |
| Boiling point | 20.2 °C |
| Critical temperature | 188 °C at 6.4 MPa |
| Viscosity | ~0.215 at 20 °C |
| Structure | |
| Molecular shape | trigonal planar (sp2) at C1 tetrahedral (sp3) at C2 |
| Dipole moment | 2.7 D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Very flammable (F+) Harmful (Xn) Carc. Cat. 3 |
| NFPA 704 |
4
2
2
|
| R-phrases | R12, R36/37, R40 |
| S-phrases | S2, S16, S33, S36/37 |
| Flash point | −39 °C |
| Autoignition temperature | 185 °C |
| RTECS number | AB1925000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behavior Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related aldehydes | Formaldehyde Propionaldehyde Ethylene oxide |
| Disclaimer and references | |
Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula CH3CHO (or MeCHO). It is a flammable liquid with a fruity smell. It occurs naturally in ripe fruit, coffee, and fresh bread and is produced by plants as part of their normal metabolism. It is perhaps best known as the chemical that causes "hangovers." In the chemical industry, acetaldehyde is used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals.
Ethenol
Traces of acetaldehyde exist in the enol form, ethenol, with Keq = 6 x 10-5.[1] Ethenol has been detected in the interstellar medium.
Applications in Organic Synthesis
Acetaldehyde is a common 2-carbon building block in organic synthesis.[2] Because of its small size and its availability as the anhydrous monomer (unlike formaldehyde), it is a common electrophile. With respect to its condensation reactions, acetaldehyde is prochiral. It is mainly used as a source of the CH3C+H(OH) synthon in aldol and related condensation reactions.[3] Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives.[4] In one of the more spectacular condensation reactions, three equivalents of formaldehyde add to MeCHO to give pentaerythritol, C(CH2OH)4.[5]
In a Strecker reaction, acetaldehyde condenses with cyanide and ammonia to give, after hydrolysis, the amino acid alanine.[6] Acetaldehyde can condense with amines to yield imines, such as the condensation with cyclohexylamine to give N-ethylidenecyclohexylamine. These imines can be used to direct subsequent reactions like an aldol condensation.[7]
It is also an important building block for the synthesis of heterocyclic compounds. A remarkable example is its conversion upon treatment with ammonia to 5-ethyl-2-methylpyridine ("aldehyde-collidine”).[8]
Acetal Derivatives
Three molecules of acetaldehyde condense to form “paraldehyde,” a cyclic trimer containing C-O single bonds; four condense to form the cyclic molecule called metaldehyde.
Acetaldehyde forms a stable acetal upon reaction with ethanol under conditions that favor dehydration. The product, CH3CH(OCH2CH3)2, is in fact called "acetal," although acetal is used more widely to describe other compounds with the formula RCH(OR')2.[9]
Biological Aspects
In the liver, the enzyme alcohol dehydrogenase converts ethanol into acetaldehyde, which is then further converted into harmless acetic acid by acetaldehyde dehydrogenase. The last steps of alcoholic fermentation in bacteria, plants, and yeast involve the conversion of pyruvate into acetaldehyde by the enzyme pyruvate decarboxylase, followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction.
Acetaldehyde and Hangovers
Most people of East Asian descent have a mutation in their alcohol dehydrogenase gene that makes this enzyme unusually effective at converting ethanol to acetaldehyde, and about half of such people also have a form of acetaldehyde dehydrogenase which is less effective at converting acetaldehyde to acetic acid. [10] This combination causes them to suffer from the alcohol flush reaction, in which acetaldehyde accumulates after drinking, leading to severe and immediate hangover symptoms. These people are therefore less likely to become alcoholics. The drug Antabuse (disulfiram) also prevents the oxidation of acetaldehyde to acetic acid, with the same unpleasant effects for drinkers. It has been used in the treatment of alcoholism.
Other Occurrences
Acetaldehyde is an air pollutant resulting from combustion, such as automotive exhaust and tobacco smoke, contributing to the addictive properties of tobacco.
Safety
Acetaldehyde is a toxin, an irritant, and a probable carcinogen.
See Also
Notes
- ↑ Jerry March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (Wiley; 4 edition, 1992, ISBN 978-0471581482).
- ↑ Leo A. Paquette, David Crich, Philip L. Fuchs, and Gary A. Molander (eds.), Encyclopedia of Reagents for Organic Synthesis (Wiley, 2009, ISBN 978-0470017548).
- ↑ Behrens, C., and Paquette, L.A., “N-Benzyl-2,3-Azetidinedione.” Organic Syntheses, Collected Volume 10. 2004, 41.
- ↑ Walter, L.A., “1-(α-Pyridyl)-2-Propanol” Organic Syntheses, Collected Volume 3. 1955, 757.
- ↑ Schurink, H. B. J., “Pentaerythritol.” Organic Syntheses, Collected Volume 1. 1941, 425.
- ↑ Kendall, E.C., and McKenzie, B.F., “dl-Alanine.” Organic Syntheses, Collected Volume 1. 1941, 21.
- ↑ Georg Wittig and A. Hesse, “Directed Aldol Condensations: β-Phenylcinnamaldehyde” Organic Syntheses, Collected Volume 6. 1988, 901.
- ↑ R.L. Frank, F.J. Pilgrim, and E.F. Riener, “5-Ethyl-2-Methylpyridine” Organic Syntheses, Collected Volume 4. 1963, 451.
- ↑ H. Adkins and B.H. Nissen, “Acetal” Organic Syntheses, Collected Volume 1. 1941, 1.
- ↑ Q. Xiao, H. Weiner, and D.W. Crabb, “The Mutation in the Mitochondrial Aldehyde Dehydrogenase (ALDH2) Gene Responsible for Alcohol-Induced Flushing Increases Turnover of the Enzyme Tetramers in a Dominant Fashion.” J. Clin. Invest. 1996, 2027-2032. Retrieved April 3, 2018.
ReferencesISBN links support NWE through referral fees
- March, Jerry. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley; 4 edition, 1992. ISBN 978-0471581482
- McMurry, John. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole. 2004. ISBN 0534420052
- Morrison, Robert T., and Boyd, Robert N. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice Hall. 1992. ISBN 0136436692
- Paquette, Leo A., David Crich, Philip L. Fuchs, and Gary A. Molander (eds.). Encyclopedia of Reagents for Organic Synthesis. Wiley, 2009. ISBN 978-0470017548
- Solomons, T.W. Graham, and Fryhle, Craig B. Organic Chemistry. 8th ed. Hoboken, NJ: John Wiley. 2004. ISBN 0471417998
External Links
All links retrieved June 14, 2023.
- National Institute for Occupational Safety and Health. NIOSH Pocket Guide to Chemical Hazards.
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