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Iodoform
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==Synthesis and reactions== The synthesis of iodoform was first described by [[Georges-Simon Serullas]] in 1822, by reactions of iodine vapour with steam over red-hot coals, and also by reaction of potassium with ethanolic iodine in the presence of water;<ref>{{citation| first = Georges-Simon|last = Surellas| url = http://gallica.bnf.fr/ark:/12148/bpt6k6137757n/f2.image |title = Notes sur l'Hydriodate de potasse et l'Acide hydriodique. -- Hydriodure de carbone; moyen d'obtenir, à l'instant, ce composé triple|trans-title= Notes on the hydroiodide of potassium and on hydroiodic acid -- hydroiodide of carbon; means of obtaining instantly this compound of three elements| language = French| publisher = Metz, France: Antoine| year= 1822| pages= 17–20, 28–29}}</ref> and at much the same time independently by [[John Thomas Cooper]].<ref name=ODNB>{{cite ODNB|last=James|first=Frank A. J. L.|title=Cooper, John Thomas |url=http://www.oxforddnb.com/view/article/39361 |access-date=26 January 2012 |doi=10.1093/ref:odnb/39361|year=2004}}</ref> It is synthesized in the [[haloform reaction]] by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds: a methyl [[ketone]] ({{chem2|CH3COR}}), [[acetaldehyde]] ({{chem2|CH3CHO}}), [[ethanol]] ({{chem2|CH3CH2OH}}), and certain secondary [[Alcohol (chemistry)|alcohol]]s ({{chem2|CH3CHROH}}, where R is an alkyl or aryl group). :[[Image:Iodoform synthesis.svg|450px|class=skin-invert-image]] The reaction of iodine and base with [[methyl]] [[ketone]]s is so reliable that the [[iodoform test]] (the appearance of a yellow precipitate) is used to probe the presence of a methyl ketone. This is also the case when testing for specific [[secondary alcohol]]s containing at least one [[methyl]] group in [[Alpha and beta carbon|alpha-position]]. Some reagents (e.g. [[hydrogen iodide]]) convert iodoform to [[diiodomethane]]. Conversion to [[carbon dioxide]] is also possible.<ref>{{cite journal |doi= 10.1021/ja01129a067 |title= A Method for the Specific Conversion of Iodoform to Carbon Dioxide |journal= J. Am. Chem. Soc. |year= 1952 |volume= 74 |issue= 9 |pages= 2404 |first1= W. W. |last1= Shreeve |first2= F. |last2= Leaver |first3= I. |last3= Siegel |bibcode= 1952JAChS..74.2404S }}</ref> Iodoform reacts with aqueous [[silver nitrate]] to produce [[carbon monoxide]]. When treated with powdered elemental silver the iodoform is reduced, producing [[acetylene]]. Upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon. ===Natural occurrence=== The [[angel's bonnet]] mushroom contains iodoform, and shows its characteristic odor.
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