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Dehydration reaction

This article is about chemical reactions resulting in the loss of water from a molecule. For the removal of water from solvents and reagents, seeDesiccation.

Inchemistry, adehydration reaction is achemical reaction that involves the loss H2O from the reactingmolecule(s) orion(s). This reaction results in the release of the H2O aswater. When the reaction involves the coupling of two molecules into a single molecule it is referred to as acondensation reaction. Dehydration reactions are common processes in the manufacture of chemical compounds as well as naturally occurring within living organisms.

The reverse of a dehydration reaction is called ahydration reaction. The reverse of a condensation reaction yielding water is calledhydrolysis.

Condensation reactions occurring in living organisms

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Condensation dehydration reactions are fundamental to the existence of life as this type of reaction produces proteins fromamino acids,DNA andRNA fromnucleotides,fats fromfatty acids, andpolysaccharides (eg. cellulose, starch, sugar, lactose) from monosaccharides (eg. glucose and fructose).

The formation of thepyrophosphate bond is an important dehydration reaction relevant to bioenergetics.Phosphorylation is a type of condensation dehydration reaction that is widely used to catalyze condensation reactions in living organisms. This phosphorylation usually involves the simultaneous dephosphorylation ofATP and therefore does not result in the release of H2O.

These reactions are all mediated byenzymes.

Condensation dehydration reactions in organic chemistry

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Esterification

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The classic example of a dehydration reaction is theFischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester

RCO2H + R′OH ⇌ RCO2R′ + H2O

Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.

Etherification

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Twomonosaccharides, such asglucose andfructose, can be joined together (to formsaccharose) using dehydration synthesis. The new molecule, consisting of two monosaccharides, is called adisaccharide.

Dehydration reactions in organic chemistry resulting in unsaturated bonds

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Nitrile formation

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Nitriles are often prepared by dehydration of primary amides.

RC(O)NH2 → RCN + H2O

Ketene formation

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Ketene is produced by heatingacetic acid and trapping the product:[1]

CH3CO2H → CH2=C=O + H2O

Alkene formation

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Alkenes can be made from alcohols by dehydration. This conversion, among others, is used in converting biomass to liquid fuels.[2] The conversion of ethanol toethylene is a fundamental example:[3][4]

   CH3CH2OH → H2C=CH2 + H2O

The reaction is accelerated byacid catalysts such assulfuric acid and certainzeolites.These reactions often proceed viacarbocation intermediates as shown for the dehydration ofcyclohexanol.[5]

 
 

Some alcohols are prone to dehydration. 3-Hydroxylcarbonyls, calledaldols, release water upon standing at room temperature:

RC(O)CH2CH(OH)R' → RC(O)CH=CHR' + H2O

The reaction is induced by dehydrating reagents. For example, 2-methyl-cyclohexan-1-ol dehydrates to 1-methylcyclohexene in the presence ofMartin's sulfurane, which reacts irreversibly with water.[6][7]

Double dehydration is illustrated by the conversion ofglycerol toacrolein:[8][9]

 

Dehydration reactions in inorganic chemistry

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Various construction materials are produced by dehydration.Plaster of Paris is produced by dehydration ofgypsum in a kiln:[10][11]

CaSO42H2O+{\displaystyle {\ce {CaSO4.2H2O +{}}}} heat{\displaystyle {\ce {->}}} CaSO412H2O+112H2O{\displaystyle {\ce {CaSO4.1/2H2O + 1 1/2H2O}}} (released as steam).

The resulting dry powder is ready to be mixed with water to form a stiff but workable paste that hardens.


References

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  1. ^Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a15_063.ISBN 3527306730.
  2. ^Besson, Michèle; Gallezot, Pierre; Pinel, Catherine (2014-02-12)."Conversion of Biomass into Chemicals over Metal Catalysts".Chemical Reviews.114 (3):1827–1870.doi:10.1021/cr4002269.ISSN 0009-2665.PMID 24083630.
  3. ^Zimmermann, Heinz; Walz, Roland (2008). "Ethylene".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a10_045.pub3.ISBN 978-3527306732.
  4. ^Zhang, Minhua; Yu, Yingzhe (2013-07-17)."Dehydration of Ethanol to Ethylene".Industrial & Engineering Chemistry Research.52 (28):9505–9514.doi:10.1021/ie401157c.ISSN 0888-5885.
  5. ^G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene".Organic Syntheses.5: 33.doi:10.15227/orgsyn.005.0033.
  6. ^J. Brent Friesen; Robert Schretzman (2011). "Dehydration of 2-Methyl-1-cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment".J. Chem. Educ.88 (8):1141–1147.Bibcode:2011JChEd..88.1141F.doi:10.1021/ed900049b.
  7. ^Roden, Brian A. (2001). "Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-propoxy)sulfurane".Encyclopedia of Reagents for Organic Synthesis.doi:10.1002/047084289X.rd409.ISBN 0471936235.
  8. ^H. Adkins; W. H. Hartung (1926). "Acrolein".Organic Syntheses.6: 1.doi:10.15227/orgsyn.006.0001.
  9. ^Katryniok, Benjamin; Paul, Sébastien; Bellière-Baca, Virginie; Rey, Patrick; Dumeignil, Franck (2010)."Glycerol dehydration to acrolein in the context of new uses of glycerol".Green Chemistry.12 (12): 2079.doi:10.1039/c0gc00307g.ISSN 1463-9262.
  10. ^Franz Wirsching "Calcium Sulfate" in Ullmann's Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH, Weinheim.doi:10.1002/14356007.a04_555
  11. ^Staff."CaSO4, ½ H2O".LaFargePrestia. Archived fromthe original on November 20, 2008. Retrieved27 November 2008.

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