Re: ORGLIST: Synthesis of alkyl halides

From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Tue Dec 11 2001 - 03:17:07 EST

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Hello Alejandro,

The explanation is a bit lengthy, as it has to do with various phenomena:
the inductive and steric effects of the substituents on the C carrying the
OH group, electrophilic catalysis of nucleophilic substitutions, the
differences between SN1 and SN2 mechanisms of nucleophilic substitution.
Take any good textbook of organic chemistry and all these phenomena and the
particular reactions you are interested in will be clearly explained.

All the best,

Jacob

At 19:29 9/12/1, Alejandro Lalo wrote:
>Dear members:
>In the synthesis of tert-butyl chloride from
>tert-butanol the alcohol reacts with HCl at room
>temperature. However, to synthesize n-butyl chloride
>from n-butanol I must use HCl and ZnCl2 and heat the
>reaction mixture. I want to know which is the
>mechanism in the second case and what is the function
>of the ZnCl2 in the reaction?
>
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Prof. Jacob Zabicky
Institutes for Applied Research
Ben-Gurion University of the Negev Private: POB 12366, Beer-Sheva 84863
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