Master Organic Chemistry Reaction Guide

Conversion of alcohols to alkyl halides using HCl

Description: Treatment of tertiary alcohols with HCl leads to formation of tertiary alkyl chlorides.

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Real-Life Example:

Org. Synth. 1925, 5, 27
DOI Link: 10.15227/orgsyn.005.0027

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Org. Synth. 1928, 8, 50
DOI Link: 10.15227/orgsyn.008.0050

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Org. Synth. 1948, 28, 65
DOI Link: 10.15227/orgsyn.028.0065

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Org. Synth. 1956, 36, 50
DOI Link: 10.15227/orgsyn.036.0050

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Comment section

8 thoughts on “Conversion of alcohols to alkyl halides using HCl

    1. Great question! Alcohols don’t have a good leaving group, so they don’t undergo substitution or elimination (except under acidic conditions). However once you convert them to alkyl chlorides, you can then turn them into all kinds of other useful functional groups.

    1. You get a mixture of retention and inversion, which leads to a mixture of enantiomers. I updated the image to make it more clear. Thanks for asking.

  1. Although you get a mixture of enantiomers when a chiral carbon is attacked like in example 3 is there a slight preference for the inversion? Or do you get each at roughly 50 50?

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