Regioselectivity

Regioselectivity

In chemistry, regioselectivity is the preference of one direction of chemical bond making or breaking over all other possible directions [JerryMarch] [http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch06/ch6-0-1.html Regioselectivity & Stereoselectivity] . It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will add.

A specific example is a halohydrin formation reaction with 2-propenylbenzene ["Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene" Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy 102 Journal of Chemical Education • Vol. 85 No. 1 January 2008] :

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The reaction product is a mixture of two isomers and the regioselectivity is said to be poor.

Regioselectivity in ring-closure reactions is subject to Baldwin's rules.

ee also

* Cryptoregiochemistry

References


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