Editing Amyl nitrite (section)

==Synthesis and reactions==
Alkyl nitrites are prepared by the reaction of [[Alcohol (chemistry)|alcohol]]s with [[nitrous acid]]:<ref>{{OrgSynth | vauthors = Noyes WA |author-link=William A. Noyes |year=1943 |title=n-Butyl Nitrite |volume= |pages= |collvol=2 |collvolpages=108 |prep=CV2P0108}}</ref>

:ROH  +  HONO  →  RONO  +  H<sub>2</sub>O, where R = alkyl group

The reaction is called [[esterification]]. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated [[sulfuric acid]] to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrogen dioxide and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily [[Decantation|decanted]] from the reaction mixture.

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the [[Amyl alcohol|isoamyl alcohol]]:
:C<sub>5</sub>H<sub>11</sub>ONO  +  NaOH  → C<sub>5</sub>H<sub>11</sub>OH  +  [[sodium nitrite|NaNO<sub>2</sub>]]

Amyl nitrite, like other alkyl nitrites, reacts with [[carbanion]]s to give [[oxime]]s.<ref>{{OrgSynth | vauthors = Chen YK, Jeon SJ, Walsh PJ, Nugent WA | title = (2S)-(−)-3-exo-(Morpholino)isoborneol ((−)-MIB) | volume = 82 | pages = 87 | year = 2005 | prep = v82p0087}}</ref>

Amyl nitrites are also useful as reagents in a modification of the [[Sandmeyer reaction]].  The reaction of the alkyl nitrite with an aromatic [[amine]] in a halogenated solvent produces a [[radical (chemistry)|radical]] aromatic species, this then frees a [[halogen]] atom from the solvent.  For the synthesis of [[Organoiodine compound|aryl iodide]]s [[diiodomethane]] is used,<ref>{{cite journal | vauthors = Smith WB, Ho OC | title = Application of the isoamyl nitrite-diiodomethane route to aryl iodides | journal = The Journal of Organic Chemistry | volume = 55 | pages = 2543–2545 | year = 1990 | doi = 10.1021/jo00295a056 | issue = 8 }}</ref><ref>{{cite journal | vauthors = Cornforth J, Kumar A, Stuart AS | title = Synthesis of substituted dibenzophospholes. Part 6. Preparation of symmetrical and non-symmetrical quaterphenyl intermediates | journal = Journal of the Chemical Society, Perkin Transactions 1 | page = 859 | year = 1987 | doi = 10.1039/P19870000859}}</ref> whereas [[bromoform]] is the solvent of choice for the synthesis of [[Organobromine compound|aryl bromide]]s.<ref>{{cite journal | vauthors = Cadogan JI, Roy DA, Smith DM | title = An alternative to the Sandmeyer reaction | journal = Journal of the Chemical Society C: Organic | page = 1249 | year = 1966 | doi = 10.1039/J39660001249}}</ref>