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In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitutio?

jojo1995

In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitution?
thanks :smile:

Reply 1

Puddles the Monkey

Original post by jojo1995

In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitution?
thanks :smile:

Heya, I'm going to put this in the chemistry forum for you as you should get more responses there. :smile:

You should also check out the forum to see if there's any other threads there which might be helpful to you!

http://www.thestudentroom.co.uk/forumdisplay.php?f=130

Reply 2

charliebe2

Original post by jojo1995

In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitution?
thanks :smile:

I'm not quite sure what you mean by that, can you number the carbons on a benzene ring if it doesn't have a functional group?

Reply 3

langlitz

Original post by jojo1995

In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitution?
thanks :smile:

Only if there is an electron donating group or a halogen on the ring already... Benzene itself (as said above) cannot be numbered

Reply 4

charliebe2

Original post by langlitz

Only if there is an electron donating group or a halogen on the ring already... Benzene itself (as said above) cannot be numbered

Yeah, you only number when you have a relevant functional group, a good example of which would be phenol. I'm assuming that 2,4,6 become the most likely locations for substitutions as they will provide the most stable configuration.

Reply 5

langlitz

Original post by charliebe2

Original post by jojo1995

In benzene, why are carbons 2,4 and 6 more susceptible to electrophillic substitution?
thanks :smile:

It's because of the of the increased stability of the transition state in these positions for a electron donating group (more resonance structures). Anything which can stabilise this carbocation will lower the energy of the transition state