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Concept
Iodoform
Summary
Iodoform (also known as triiodomethane) is the organoiodine compound with the chemical formula . It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.
Iodoform is incorrectly called carbon triiodide, incorrectly because "carbon triiodide" could mean or and (hexaiodoethane), ignoring the hydrogen atom in the iodoform molecule, which implies a trivalent or monovalent carbon in iodoform, which is incorrect. Instead of that incorrect name, the correct names of iodoform or triiodomethane should be used.
The molecule adopts tetrahedral molecular geometry with C3v symmetry.
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; and at much the same time independently by John Thomas Cooper. 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 (), acetaldehyde (), ethanol (), and certain secondary alcohols (, where R is an alkyl or aryl group).
The reaction of iodine and base with methyl ketones 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 alcohols containing at least one methyl group in alpha-position.
Some reagents (e.g. hydrogen iodide) convert iodoform to diiodomethane. Also conversion to carbon dioxide is possible: 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.
Official source
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