Editing Nitro compound (section)

====Ter Meer Reaction====
In [[nucleophilic substitution|nucleophilic aliphatic substitution]], [[sodium nitrite]] (NaNO<sub>2</sub>) replaces an [[alkyl halide]]. In the so-called Ter Meer reaction (1876) named after [[Edmund ter Meer]],<ref>{{cite journal
 | author = Edmund ter Meer
 | title = Ueber Dinitroverbindungen der Fettreihe
 | journal = [[Liebigs Annalen|Justus Liebigs Annalen der Chemie]]
 | volume = 181
 | issue = 1
 | pages = 1–22
 | year = 1876
 | doi = 10.1002/jlac.18761810102| url = https://zenodo.org/record/1427353
 | author-link = Edmund ter Meer
 }}</ref> the reactant is a 1,1-halonitroalkane:
:[[File:Ter Meer Reaction.svg|class=skin-invert-image|The ter Meer reaction]]

The [[reaction mechanism]] is proposed in which in the first slow step a [[Hydron (chemistry)|proton]] is abstracted from nitroalkane '''1''' to a [[carbanion]] '''2''' followed by [[protonation]] to an aci-nitro '''3''' and finally [[nucleophilic displacement]] of chlorine based on an experimentally observed hydrogen [[kinetic isotope effect]] of 3.3.<ref>{{cite journal |doi=10.1021/ja01600a048 |title=Aci-Nitroalkanes. I. The Mechanism of the ter Meer Reaction1 |journal=Journal of the American Chemical Society |volume=78 |issue=19 |pages=4980–4984 |year=1956 |last1=Hawthorne |first1=M. Frederick}}</ref> When the same reactant is reacted with [[potassium hydroxide]] the reaction product is the 1,2-dinitro dimer.<ref>''3-Hexene, 3,4-dinitro-'' D. E. Bisgrove, J. F. Brown, Jr., and L. B. Clapp. ''[[Organic Syntheses]]'', Coll. Vol. 4, p. 372 (1963); Vol. 37, p. 23 (1957). ([http://www.orgsynth.org/orgsyn/pdfs/CV4P0372.pdf Article])</ref>