Editing Nitro compound (section)

==Synthesis==
===Preparation of aromatic nitro compounds ===
[[File:PhNO2&metric.png|class=skin-invert-image|thumb|144px|Structural details of [[nitrobenzene]], distances in picometers.<ref>{{cite journal |journal=Structural Chemistry |year=2007 |volume=18 |issue=6 |pages=739–753 |title=Molecular Structure and Conformation of Nitrobenzene Reinvestigated by Combined Analysis of Gas-Phase Electron Diffraction, Rotational Constants, and Theoretical Calculations |author=Olga V. Dorofeeva |author2=Yuriy V. Vishnevskiy |author3=Natalja Vogt |author4=Jürgen Vogt |author5=Lyudmila V. Khristenko |author6=Sergey V. Krasnoshchekov |author7=Igor F. Shishkov |author8=István Hargittai |author9=Lev V. Vilkov |doi=10.1007/s11224-007-9186-6 |s2cid=98746905}}</ref>]]

Aromatic nitro compounds are typically synthesized by nitration. Nitration is achieved using a mixture of [[nitric acid]] and [[sulfuric acid]], which produce the [[nitronium]] ion ({{chem2|NO2+}}), which is the electrophile: 
<div>{{pad|1em}}[[File:Benzol.svg|class=skin-invert-image|x60px|Benzene]] + [[File:Nitronium ion vert.svg|class=skin-invert-image|x60px|Nitronium ion]] {{Biochem reaction subunit|direction=forward|for_prod={{H+|nolink=y}}|imagesize=60px|container_style=vertical-align:middle}} [[File:Nitrobenzol.svg|class=skin-invert-image|x100px|Nitrobenzene]]</div>

The nitration product produced on the largest scale, by far, is [[nitrobenzene]]. Many explosives are produced by nitration including [[trinitrophenol]] (picric acid), [[trinitrotoluene]] (TNT), and [[trinitroresorcinol]] (styphnic acid).<ref>{{Ullmann|last=Gerald|first=Booth|title=Nitro Compounds, Aromatic|doi=10.1002/14356007.a17_411}}</ref>
Another but more specialized method for making aryl–NO<sub>2</sub> group starts from halogenated phenols, is the [[Zinke nitration]].

===Preparation of aliphatic nitro compounds ===
Aliphatic nitro compounds can be synthesized by various methods; notable examples include:
*[[Free radical]] [[nitration]] of [[alkane]]s.<ref>{{cite journal|last1=Markofsky|first1=Sheldon|last2=Grace|first2=W.G.|title=Nitro Compounds, Aliphatic|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a17_401|isbn=978-3-527-30673-2}}</ref> The reaction produces fragments from the parent alkane, creating a diverse mixture of products; for instance, [[nitromethane]], [[nitroethane]], [[1-Nitropropane|1-nitropropane]], and [[2-Nitropropane|2-nitropropane]] are produced by treating [[propane]] with [[nitric acid]] in the gas phase (e.g. 350–450&nbsp;°C and 8–12 [[Atmosphere (unit)|atm]]).
*[[Nucleophilic substitution]] reactions between [[halocarbon]]s<ref>{{cite journal|last1=Kornblum|first1=N.|last2=Ungnade|first2=H. E.|title=1-Nitroöctane|journal=Organic Syntheses|date=1963|volume=4|page=724|doi=10.15227/orgsyn.038.0075}}</ref> or [[organosulfate]]s<ref>{{cite journal|last1=Walden|first1=P.|title=Zur Darstellung aliphatischer Sulfocyanide, Cyanide und Nitrokörper|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1907|volume=40|issue=3|pages=3214–3217|doi=10.1002/cber.19070400383|url=https://zenodo.org/record/1426247}}</ref> with [[Silver nitrite|silver]] or [[Alkali metal|alkali]] [[nitrite]] salts.
*Nitromethane can be produced in the laboratory by treating [[chloroacetic acid|sodium chloroacetate]] with [[sodium nitrite]].<ref>{{cite journal|last1=Whitmore|first1=F. C.|last2=Whitmore|first2=Marion G.|title=Nitromethane|journal=Organic Syntheses|date=1923|volume=1|page=401|doi=10.15227/orgsyn.003.0083}}</ref>
*[[Organic redox reaction|Oxidation]] of [[oxime]]s<ref>{{cite journal|last1=Olah|first1=George A.|last2=Ramaiah|first2=Pichika|last3=Chang-Soo|first3=Lee|last4=Prakash|first4=Surya|title=Convenient Oxidation of Oximes to Nitro Compounds with Sodium Perborate in Glacial Acetic Acid|journal=Synlett|date=1992|volume=1992|issue=4|pages=337–339|doi=10.1055/s-1992-22006}}</ref> or [[Primary (chemistry)|primary]] [[amine]]s.<ref>{{cite journal|last1=Ehud|first1=Keinan|last2=Yehuda|first2=Mazur|title=Dry ozonation of amines. Conversion of primary amines to nitro compounds|journal=The Journal of Organic Chemistry|date=1977|volume=42|issue=5|pages=844–847|doi=10.1021/jo00425a017}}</ref>
*Reduction of [[Henry reaction|β-nitro alcohols]]<ref>{{cite journal |last1=Chandrasekhar |first1=S. |last2=Shrinidhi |first2=A. |title=Useful Extensions of the Henry Reaction: Expeditious Routes to Nitroalkanes and Nitroalkenes in Aqueous Media |journal=Synthetic Communications |date=2014 |volume=44 |issue=20 |pages=3008–3018 |doi=10.1080/00397911.2014.926373|s2cid=98439096 |url=https://figshare.com/articles/journal_contribution/1053153 }}</ref> or [[nitroalkene]]s.<ref>{{cite journal |last1=Shrinidhi |first1=A. |title=Microwave-assisted chemoselective reduction of conjugated nitroalkenes to nitroalkanes with aqueous tri-n-butyltin hydride |journal=Cogent Chemistry |date=2015 |volume=1 |issue=1 |page=1061412 |doi=10.1080/23312009.2015.1061412|doi-access=free }}</ref>
*By [[decarboxylation]] of [[alpha and beta carbon|α]]-nitro [[carboxylic acid]]s formed from [[nitriles]] and [[ethyl nitrate]].<ref>{{cite journal|last1=Wislicenus|first1=Wilhelm|last2=Endres|first2=Anton|title=Ueber Nitrirung mittels Aethylnitrat [Nitrification by means of ethyl nitrate]|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1902|volume=35|issue=2|pages=1755–1762|doi=10.1002/cber.190203502106|url=https://zenodo.org/record/1426046}}</ref><ref>{{cite book|last1=Weygand|first1=Conrad|editor1-last=Hilgetag|editor1-first=G.|editor2-last=Martini|editor2-first=A.|title=Weygand/Hilgetag Preparative Organic Chemistry|date=1972|publisher=John Wiley & Sons, Inc.|location=New York|isbn=978-0-471-93749-4|page=1007|edition=4th}}</ref>

====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>