Ace Your Next Organic Chemistry Exam.

With these Downloadable PDF Study Guides

Our Study Guides

Conversion of alcohols to alkyl halides using HCl

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

Notes: This proceeds through an SN1 mechanism. The reaction also works for other alcohols that form stable carbocations, such as allylic and benzylic alcohols.

Examples: 

Notes: Note that in the third example, since a stereocenter is present, a mixture of stereoisomers (enantiomers) will be formed since the reaction proceeds through an SN1 reaction.

Mechanism:

Notes: If the alcohol were on a stereocenter we would obtain a mixture of stereoisomers.

[/private_ReactionGuide]