Master Organic Chemistry Reaction Guide

Formation of chlorohydrins from alkenes using water and Cl2

Description: Alkenes treated with chlorine (Cl2) in the presence of water will form chlorohydrins. The stereochemistry of the products is anti.

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Real-Life Example:

Org. Synth. 1953, 33, 15
DOI Link: 10.15227/orgsyn.033.0015

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20 thoughts on “Formation of chlorohydrins from alkenes using water and Cl2

  1. In the step 2, why does H2O attack not chloride ion? isn’t chloride ion more nucleophile than water? Thanks.

  2. hi , in the 3rd reaction , i checked the mechanism , based on what you choose the intra OH to attack instead of water ? thank you :)

  3. could you by any chance explain the mechanism of the 3 rxn? trying to get it and I’m not sure if the water that just attacked leaves or if the HCl adds an H to the other OH and then that leaves

        1. Hi,
          according to the mechanism drawn, should the reaction also happen without water? Chloride can act as a base in that case.

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