Re: TOJC

vantranh@plu.edu
Sun, 15 Dec 1996 16:17:57 -0800 (PST)

Kate,
in the text, on page 450, it explains this mechanism.
1) the acid readts with the epoxide to produce a protonated epoxide.
2) the protonated epoxide reacts with the weak nucleophile (water) to
form a protonated glycol, which then transfers a proton to a molecule of
water to form the glycol and a hydronium ion.
3) A strong nucleopile such as an alkoxide ion or a hydroxide ion is able
to open the strained epoxide ring in a direct Sn2 reaction.

The main difference between an acid catalyzed and a base catalyzed
ring opening is that the acid attacks at the more substituted carbon of
the epoxide ring and the base attacks at the less substituted carbon.

Good luck studying and I hope this helps some! Ta! Ta!
vantranh

On Fri, 13 Dec 1996 moehrikm@plu.edu wrote:

> hey chem people!
> i hope everyone's studying is going well. perhaps someone could
> take the time to explain the epoxide ring opening in both acids and bases.
> i think i understand the general princial but i would like to be better
> acquainted with the mechanisms. thanks again and good luck on finals!
> kate
>
>