Topic: Electrophilic aromatic substitution (Read 4328 times)

THC · « **on:** February 28, 2008, 02:21:43 PM »

I was just wondering...

When Cl2 is added to toluene, the products are typically o-bromotoluene and p-bromotoluene. But why isn't -CH3 the leaving group, so the product would be bromobenzene? Is -CH3 a bad leaving group, or what is the explanation?

azmanam · « **Reply #1 on:** February 28, 2008, 02:23:27 PM »

what do you propose the mechanism is for this reaction? that will help explain why CH₃ remains in the product.

THC · « **Reply #2 on:** February 28, 2008, 02:48:10 PM »

Ah yes, of course. Thank you once again

azmanam · « **Reply #3 on:** February 28, 2008, 02:49:45 PM »

np. and yes, CH₃^- is a terrible leaving group.

Sev · « **Reply #4 on:** February 28, 2008, 05:00:00 PM »

Quote

When Cl2 is added to toluene, the products are typically o-bromotoluene and p-bromotoluene.

Cl₂?

agrobert · « **Reply #5 on:** February 28, 2008, 05:04:25 PM »

must be confusion in OP, but I think he understands the concept which is the samne either way

THC · « **Reply #6 on:** February 29, 2008, 01:45:41 PM »

Sorry, yes, I was a bit absentminded. I should have written X2, where X is a halogen.

Topic: Electrophilic aromatic substitution (Read 4328 times)

THC

Electrophilic aromatic substitution

azmanam

Re: Electrophilic aromatic substitution

THC

Re: Electrophilic aromatic substitution

azmanam

Re: Electrophilic aromatic substitution

Sev

Re: Electrophilic aromatic substitution

agrobert

Re: Electrophilic aromatic substitution

THC

Re: Electrophilic aromatic substitution

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