SDN members see fewer ads and full resolution images. Join our non-profit community!

NBS Bromination of Toluene

Discussion in 'DAT Discussions' started by skyisblue, Mar 22, 2007.

  1. skyisblue

    skyisblue 2+ Year Member

    430
    0
    Dec 25, 2006
    NBS Bromination of Toluene leads to bromination at the benzylic position.

    However, there are like 5 resonance structures for the benzyl radical, the intermediate produced in the NBS bromination reaction of toluene.

    So, there should be bromination on the benzene ring too. Right???
     
  2. SDN Members don't see this ad. About the ads.
  3. BodybldgDoc

    BodybldgDoc Guest

    712
    0
    Jan 13, 2007
    In your closet
    No. I dont see why there would be.
     
  4. Lonely Sol

    Lonely Sol cowgoesmoo fan! 10+ Year Member

    684
    0
    Dec 13, 2005
    Atlanta, GA
    Okay, you are right, it does have 5 resonance structure, but the thing is bromine cannot go to any other carbon besides the -CH3 because, if it goes to a carbon on an aromatic ring then it would disrupt thering's resonance structure by forming diene radical (sp2) with is not stable. However, if it goes on the -CH3 group then it will not disrupt resonance structure plus it will also be stablized by an sp3 radical.
     
  5. skyisblue

    skyisblue 2+ Year Member

    430
    0
    Dec 25, 2006
    Ah ha, i see the light. thank you almighty lonelysol!
     
  6. Lonely Sol

    Lonely Sol cowgoesmoo fan! 10+ Year Member

    684
    0
    Dec 13, 2005
    Atlanta, GA
    :laugh: I am not almighty by any means!! If anything, streetwolf and bodybldgdoc are the almighty ones!
     
  7. skyisblue

    skyisblue 2+ Year Member

    430
    0
    Dec 25, 2006
    dude, i'm not pulling your leg by any means....i saw your pretest scores...:thumbup: you're going to nail it..
     
  8. Lonely Sol

    Lonely Sol cowgoesmoo fan! 10+ Year Member

    684
    0
    Dec 13, 2005
    Atlanta, GA
    Lets hope so but you know those scores can sometime be misleading!
     
  9. skyisblue

    skyisblue 2+ Year Member

    430
    0
    Dec 25, 2006
    Hey, only you know what you actually know, but if you know it you know it man. I'm gonna go back to studying.
     
  10. BodybldgDoc

    BodybldgDoc Guest

    712
    0
    Jan 13, 2007
    In your closet
    Sol's gonna get super duper high scores. He is the almighty DAT exterminator!
     
  11. Lonely Sol

    Lonely Sol cowgoesmoo fan! 10+ Year Member

    684
    0
    Dec 13, 2005
    Atlanta, GA
    Thank you guys for all the support, especially bodybldgdoc!, but doing good on a practice test at your home and doing good at a pressure environment is very different!! I am just preparing for the worst. You and skyisblue probably going kill that test!! Skyisblue always have good questions, which is good cuz it helps all the people who are on here! I am just glad you post questions on here! (Keep posting!, :D ), especially for Gchem!!

    Just need to get this DAT out of the way, cant wait till its done!
     
  12. TieuBachHo

    TieuBachHo 7+ Year Member

    212
    0
    Jul 23, 2008
    NBS reacts as a radical and will not affect the benzene ring of Toluene. It will abstracts the most less hindered proton leaving the methyl group of the Toluene to be electrophilic. The benzyl structures are more stable and hindered; thus, are difficult to access. The key point is the hindrance of the C's. Just my 2 cents.
     

Share This Page