NBS Bromination of Toluene

[skyisblue]

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???

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[BodybldgDoc]

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???

No. I dont see why there would be.

 

[Lonely Sol]

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???

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.

 

[skyisblue]

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.

Ah ha, i see the light. thank you almighty lonelysol!

 

[Lonely Sol]

Ah ha, i see the light. thank you almighty lonelysol!

I am not almighty by any means!! If anything, streetwolf and bodybldgdoc are the almighty ones!

 

[skyisblue]

I am not almighty by any means!! If anything, streetwolf and bodybldgdoc are the almighty ones!

dude, i'm not pulling your leg by any means....i saw your pretest scores...👍 you're going to nail it..

 

[Lonely Sol]

dude, i'm not pulling your leg by any means....i saw your pretest scores...👍 you're going to nail it..

Lets hope so but you know those scores can sometime be misleading!

 

[skyisblue]

Lets hope so but you know those scores can sometime be misleading!

Hey, only you know what you actually know, but if you know it you know it man. I'm gonna go back to studying.

 

[BodybldgDoc]

Sol's gonna get super duper high scores. He is the almighty DAT exterminator!

 

[Lonely Sol]

Sol's gonna get super duper high scores. He is the almighty DAT exterminator!

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!, 😀 ), especially for Gchem!!

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

 

[TieuBachHo]

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???

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.