Editing Bromine (section)

===Organobromine compounds===
{{main|Organobromine compound}}
[[File:N-Bromosuccinimide.svg|thumb|upright|Structure of [[N-Bromosuccinimide|''N''-bromosuccinimide]], a common brominating reagent in organic chemistry]]
Like the other carbon–halogen bonds, the C–Br bond is a common functional group that forms part of core [[organic chemistry]]. Formally, compounds with this functional group may be considered organic derivatives of the bromide anion. Due to the difference of electronegativity between bromine (2.96) and carbon (2.55), the carbon atom in a C–Br bond is electron-deficient and thus [[electrophilic]]. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of [[organochlorine compound|organochlorine]] and [[organoiodine compound]]s. For many applications, organobromides represent a compromise of reactivity and cost.<ref name="KO" />

Organobromides are typically produced by additive or substitutive bromination of other organic precursors. Bromine itself can be used, but due to its toxicity and volatility, safer brominating reagents are normally used, such as [[N-Bromosuccinimide|''N''-bromosuccinimide]]. The principal reactions for organobromides include [[dehydrohalogenation|dehydrobromination]], [[Grignard reaction]]s, [[Wurtz reaction|reductive coupling]], and [[nucleophilic substitution]].<ref name="KO">Ioffe, David and Kampf, Arieh (2002) "Bromine, Organic Compounds" in ''Kirk-Othmer Encyclopedia of Chemical Technology''. John Wiley & Sons. {{doi| 10.1002/0471238961.0218151325150606.a01}}.</ref>

Organobromides are the most common organohalides in nature, even though the concentration of bromide is only 0.3% of that for chloride in sea water, because of the easy oxidation of bromide to the equivalent of Br{{sup|+}}, a potent electrophile. The enzyme [[bromoperoxidase]] catalyzes this reaction.<ref>{{cite journal|doi=10.1021/ja047925p|pmid=15548002|title=Vanadium Bromoperoxidase-Catalyzed Biosynthesis of Halogenated Marine Natural Products|journal=Journal of the American Chemical Society|volume=126|issue=46|pages=15060–6|year=2004|last1=Carter-Franklin|first1=Jayme N.|last2=Butler|first2=Alison|bibcode=2004JAChS.12615060C }}</ref> The oceans are estimated to release 1–2 million tons of [[bromoform]] and 56,000 tons of [[bromomethane]] annually.<ref name="Gribble99" />

[[Image:Alkene-bromine-addition-2D-skeletal.png|upright=1.8|thumb|Bromine addition to alkene reaction mechanism]]
An old qualitative test for the presence of the [[alkene]] functional group is that alkenes turn brown aqueous bromine solutions colourless, forming a [[halohydrin|bromohydrin]] with some of the dibromoalkane also produced. The reaction passes through a short-lived strongly electrophilic [[halonium ion|bromonium]] intermediate. This is an example of a [[halogen addition reaction]].<ref name="Clayden">{{cite book | last1 = Clayden | first1 = Jonathan | author-link1 = Jonathan Clayden | last2 = Greeves | first2 = Nick | last3 = Warren | first3 = Stuart | author-link3 = Stuart Warren | title = Organic Chemistry | edition = 2nd | publisher = Oxford University Press | date = 2012 | isbn = 978-0-19-927029-3 |pages=427–9}}</ref>