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Dihydroxybenzenes

In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups (−OH) are substituted onto a benzene ring (C6H6). These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene (the ortho isomer) is commonly known as catechol, 1,3-dihydroxybenzene (the meta isomer) is commonly known as resorcinol, and 1,4-dihydroxybenzene (the para isomer) is commonly known as hydroquinone.[1]

Isomer ortho meta para
Trivial name Catechol Resorcinol Hydroquinone
IUPAC name benzene-1,2-diol benzene-1,3-diol benzene-1,4-diol
Other names pyrocatechol
1,2-dihydroxybenzene
o-dihydroxybenzene
o-benzenediol
resorcin
1,3-dihydroxybenzene
m-dihydroxybenzene
m-benzenediol
1,4-dihydroxybenzene
p-dihydroxybenzene
p-benzenediol
Structure

All three of these compounds are colorless to white granular solids at room temperature and pressure, but upon exposure to oxygen they may darken. All three isomers have the chemical formula C6H6O2.

Similar to other phenols, the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic. Each benzenediol can lose an H+ from one of the hydroxyls to form a type of phenolate ion.

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (−CH=O) or ketone (>C=O) reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group (C=O) is oxidized, and the hydrogen peroxide is reduced.

See also edit

References edit

  1. ^ Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2.

dihydroxybenzenes, organic, chemistry, dihydroxybenzenes, benzenediols, organic, compounds, which, hydroxyl, groups, substituted, onto, benzene, ring, c6h6, these, aromatic, compounds, classed, phenols, there, three, structural, isomers, dihydroxybenzene, orth. In organic chemistry dihydroxybenzenes benzenediols are organic compounds in which two hydroxyl groups OH are substituted onto a benzene ring C6H6 These aromatic compounds are classed as phenols There are three structural isomers 1 2 dihydroxybenzene the ortho isomer is commonly known as catechol 1 3 dihydroxybenzene the meta isomer is commonly known as resorcinol and 1 4 dihydroxybenzene the para isomer is commonly known as hydroquinone 1 Isomer ortho meta para Trivial name Catechol Resorcinol Hydroquinone IUPAC name benzene 1 2 diol benzene 1 3 diol benzene 1 4 diol Other names pyrocatechol1 2 dihydroxybenzeneo dihydroxybenzeneo benzenediol resorcin1 3 dihydroxybenzenem dihydroxybenzenem benzenediol 1 4 dihydroxybenzenep dihydroxybenzenep benzenediol Structure All three of these compounds are colorless to white granular solids at room temperature and pressure but upon exposure to oxygen they may darken All three isomers have the chemical formula C6H6O2 Similar to other phenols the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic Each benzenediol can lose an H from one of the hydroxyls to form a type of phenolate ion The Dakin oxidation is an organic redox reaction in which an ortho or para hydroxylated phenyl aldehyde CH O or ketone gt C O reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate Overall the carbonyl group C O is oxidized and the hydrogen peroxide is reduced See also editTrihydroxybenzenes Tetrahydroxybenzenes Pentahydroxybenzene Hexahydroxybenzene Methylbenzenediols dihydroxytoluenes 3 Methylcatechol 3 methylbenzene 1 2 diol 4 Methylcatechol 4 methylbenzene 1 2 diol Orcinol 5 methylbenzene 1 3 diol Methoxyphenols can be derived from benzenediols by O methylation Guaiacol 2 methoxyphenol O Methylcatechol Mequinol 4 Methoxyphenol Dimethoxybenzenes can be derived from benzenediols by two rounds of O methylation Veratrole 1 2 Dimethoxybenzene 1 3 Dimethoxybenzene 1 4 DimethoxybenzeneReferences edit Helmut Fiege Heinz Werner Voges Toshikazu Hamamoto Sumio Umemura Tadao Iwata Hisaya Miki Yasuhiro Fujita Hans Josef Buysch Dorothea Garbe Wilfried Paulus 2002 Phenol Derivatives Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a19 313 ISBN 978 3 527 30673 2 nbsp This set index article lists chemical compounds articles associated with the same name If an internal link led you here you may wish to change the link to point directly to the intended article Retrieved from https en wikipedia org w index php title Dihydroxybenzenes amp oldid 1178163011, wikipedia, wiki, book, books, library,

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