Re: Reaction Question

-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

Hikaru wrote:

> Hi. I have this problem here. It involves 1,3 butadiene reacting with an
> equal amount of HCl. What is the major product coming out of it?
>
> I worked it out and I'm thinking the double bond will abstract the proton,
> and so the proton ends up on the outer edge (carbon 1 or 4) and then there
> is a carbocation. So chlorine could attack there, so you have
> 3-chloro-1-butene (I'm not sure if I named it correctly). Otherwise the
> intermediate could resonate and the positive charge ends up on the end, so
> you get 1-chloro-2-butene. So between those two, which is the major
> product? I initially thought 3-chloro-1-butene, but because I think I've
> named it incorrectly, that's why it's the wrong answer choice.
>
> Thank you.

Perhaps steric effects cause the chloride to prefer the terminal position to
form 1-chloro-but-2-ene, with the trans isomer presumably being preferred.

However, even if this is the case, it is quite possible that
3-chloro-but-1-ene is more abundant than either of the isomers of
1-chloro-but-2-ene taken individually


-----BEGIN PGP SIGNATURE-----
Version: GnuPG v1.4.1-ecc0.1.6 (GNU/Linux)

iD8DBQFC/Lfq/K0FHUGBi80RAj6nAJ9HNsaK4iqZqsyent5honuT8QChhQCfdsoP
1r/BiTmUp1pk335zaNaGbhY=
=GQbA
-----END PGP SIGNATURE-----
.

Relevant Pages

  • Re: copper etching
    ... when the liquid is heated somewhat. ... it did not mention the reaction of HCl with H2O2 ... instead it was written that elemental chlorine is reduced to ...
    (sci.chem)
  • Re: Acetone + ccHCl yields chlorine?
    ... HCl in order to precipitate proteins from serum. ... There seems to be a weak smell of chlorine as ... don't think acetone itself cold oxidize Cl- to elementary chlorine. ... What you are observing is the pinacol coupling reaction of acetone. ...
    (sci.chem)
  • Re: copper etching
    ... > even at a high rate, but HCl should be at excess. ... With excess H2O2 no ... There could be species which might have been formed containing chlorine ...
    (sci.chem)
  • Re: Alcohol Based flames
    ... Why people are adding Lithium carbonate to Methanol and then ... Hydroxide Solution to neutralize the chlorine solution or do I go on ... working Lithium Carbonate to react with HCL for red color flame to ber ...
    (rec.pyrotechnics)