Hey there! Sign in to join this conversationNew here? Join for free
    • Thread Starter
    Offline

    16
    ReputationRep:
    Name:  ccccccccc.jpg
Views: 17
Size:  77.6 KB Hi, I am stuck on part c of this question. I have done a and b already, and found that there are 4 isomers. However, for b I get that A is 1,4-dimethylbenzene as this can only direct NO2+ to the second carbon as the 4th carbon is already bonded to a group. However, why can't A be 1,2-dimethylbenzene because this can only form 1 product as well (1,2-dimethyl-4-nitrobenzene)

    Thanks
    • Thread Starter
    Offline

    16
    ReputationRep:
    Why can't this isomer be A? This can only direct the NO2+ electrophile to carbon 4Name:  xoxoxo.png
Views: 16
Size:  11.4 KB
    • Community Assistant
    • Study Helper
    Offline

    14
    ReputationRep:
    Community Assistant
    Study Helper
    (Original post by coconut64)
    Why can't this isomer be A? This can only direct the NO2+ electrophile to carbon 4Name:  xoxoxo.png
Views: 16
Size:  11.4 KB
    As the methyl group is 2,4,6 directing, with 1,2-dimethylbenzene there is equal possibility of substitution in the 3 and 4 positions. as both are ortho to a methyl group.
    • Thread Starter
    Offline

    16
    ReputationRep:
    (Original post by charco)
    As the methyl group is 2,4,6 directing, with 1,2-dimethylbenzene there is equal possibility of substitution in the 3 and 4 positions. as both are ortho to a methyl group.
    Oh okay, I think I get it now. So because
    1,2-dimethylbenzene is asymmetrical, ther can be multisubstitution, whereas 1,4-dimethylbenzene is symmetrical. Thanks!
 
 
 
  • See more of what you like on The Student Room

    You can personalise what you see on TSR. Tell us a little about yourself to get started.

  • Poll
    Would you like to hibernate through the winter months?
  • See more of what you like on The Student Room

    You can personalise what you see on TSR. Tell us a little about yourself to get started.

  • The Student Room, Get Revising and Marked by Teachers are trading names of The Student Room Group Ltd.

    Register Number: 04666380 (England and Wales), VAT No. 806 8067 22 Registered Office: International House, Queens Road, Brighton, BN1 3XE

    Quick reply
    Reputation gems: You get these gems as you gain rep from other members for making good contributions and giving helpful advice.