November 24, 2024, 08:31:31 AM
Forum Rules: Read This Before Posting


Topic: Wohl Ziegler reaction  (Read 3393 times)

0 Members and 1 Guest are viewing this topic.

Offline kirushanth

  • Regular Member
  • ***
  • Posts: 32
  • Mole Snacks: +1/-0
Wohl Ziegler reaction
« on: August 05, 2012, 09:46:22 AM »
In allylic bromination using NBS, why is that low concentration substitutes in allylic position?

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Wohl Ziegler reaction
« Reply #1 on: August 05, 2012, 10:30:22 AM »
In allylic bromination using NBS, why is that low concentration substitutes in allylic position?

Have a look here:
http://www.organic-chemistry.org/namedreactions/wohl-ziegler-reaction.shtm
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline camptzak

  • Full Member
  • ****
  • Posts: 159
  • Mole Snacks: +12/-11
Re: Wohl Ziegler reaction
« Reply #2 on: August 05, 2012, 02:18:33 PM »
would it do something different in high concentration of NBS?

it seems like the allylic position is the most readily attacked due to resonace stabilization.
but maybe in higher concentrations Br radical attack the allylic position and then there is still some Br2 left to attack the double bond?

and then maybe if there really a great molar excess of Br2 with hv initiation the bromine radicals would start ripping hydrogens off the carbon chain?
"Chance favors the prepared mind"
-Louis Pasteur

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Wohl Ziegler reaction
« Reply #3 on: August 05, 2012, 02:21:13 PM »
would it do something different in high concentration of NBS?

it seems like the allylic position is the most readily attacked due to resonace stabilization.
but maybe in higher concentrations Br radical attack the allylic position and then there is still some Br2 left to attack the double bond?

and then maybe if there really a great molar excess of Br2 with hv initiation the bromine radicals would start ripping hydrogens off the carbon chain?


A quote from the link "It is very important to keep the concentration of Br2 and HBr low to prevent side reactions derived from simple ionic addition with the alkene."
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Sponsored Links