Conversion of alcohols to alkyl halides using HCl

by James

Description: Treatment of tertiary alcohols with HCl leads to formation of tertiary alkyl chlorides.
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{ 5 comments… read them below or add one }

Sumera February 15, 2012 at 10:48 pm

What are the benefits or importance of converting alcohols to alkyl chlorides?


james February 16, 2012 at 12:52 am

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.


Rashmi Singh March 24, 2012 at 7:41 pm

For the third example, does chirality remain or change?


james March 25, 2012 at 12:30 pm

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.


Robert Eursiriwan November 7, 2015 at 4:53 pm

In the third example, which product is favored?


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