Re: tojc: 10.34

casmiedm@plu.edu
Fri, 06 Dec 1996 12:34:15 -0800 (PST)

Shana,
The compound you are dealing with is 1-bromobutane, a primary
alkyl halide. In primary alkyl halides, an elimation reaction is favored
if you use a strong, bulky base, such as the (CH3)3COK provided by the
solutions manual. If a less hindered base is used, such as EtONa, or a
string nucleophile, a substitution (Sn2) reaction is favored. Using this
bulky base helps you to achieve your desired product, 1-butene.
Hope this clears up the answer given.

Dan Casmier
casmiedm@plu.edu

On Fri, 6 Dec 1996 mcgillsa@plu.edu wrote:

> Hi all. Hope studying is going well... I just had a quick question. In
> this problem, (especially part b) the answer book uses (CH3)3COK as one of
> the solvents. My question is this: is this reagent really that
> important? The text didn't talk about this idea at all, other than
> problem 10.20. This idea of using RK is not hard, I just don't understand
> it as much. I was especially curious, because I used a different
> synthesis for the reaction.
>
> Please reflect if you can.
> Thanks!
> Shana M.
>
>