Master Organic Chemistry Reaction Guide

Formation of Bromohydrins from alkenes using water and Br2

Description: Alkenes treated with bromine (Br2) or N-bromosuccinimide (NBS) in the presence of water will form bromohydrins.

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Real-Life Examples:

Org. Synth. 1979, 59, 16

DOI Link: 10.15227/orgsyn.059.0016

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Org. Synth. 1977, 56, 112

DOI Link: 10.15227/orgsyn.056.0112

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Comment section

6 thoughts on “Formation of Bromohydrins from alkenes using water and Br2

  1. in the mechanism, the lone pair attacks back to the double bond (right?) and if so, does it matter which side it attacks?

  2. Is it possible to produce a halogenoalkane as a side product in this reaction, that is, Br- attacks the bromonium ion in the sec step?

    1. yes, but keep in mind the concentration of solvent is significantly higher than the concentration of the counter-ion, so it will be very small [concentration of H2O in 1L of water is 55 M!] At very high concentrations it might become more significant.

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