organic question

[mindblowing]

Advertisement - Members don't see this ad

whats the differnce between electrophilic addition and free redical addition of bromine to benzene ...i thought its same?
which one is markovniov and which one is anti markovnikov

 

[Mstoothlady2012]

whats the differnce between electrophilic addition and free redical addition of bromine to benzene ...i thought its same?
which one is markovniov and which one is anti markovnikov

electrophilic addition gives markovnikov

free radical gives non-markvonikov

 

[doc3232]

electrophilic addition gives markovnikov

free radical gives non-markvonikov

Markovnikov and anti-M doesn't apply to benzenes.
Electrophilic addition does not use radicals. Instead electrons from benzene attack the electrophile then an H leaves the ring, and electrons rebuild the aromatic ring.

 

[excusezmoi]

Electrophilic will give Markovnikov 3>2>1
Free Radical; Br is with Peroxide or ROOR it will yield to Anti-Markovinkov 1>2>3 but this is only in Br though it won't work for the others like Cl, I , F (as I remember), these guys would yield Markovnikov...somebody correct me if I'm wrong.

 

[250rsavage]

I thought Br attacks the most substituted C: Markovnikov , while Cl is anti-Markovnikov and will attack the least substituted

Or is this only for cylco rings and not benzene rings

 

[doc3232]

Benzenes are completely different than all others. I don't think there any radical reactions with benzenes on the actual ring itself. Only at the benzylic position because it is very stable.

 

[250rsavage]

This is from Kaplan BB:
in ROOR (peroxide), Br disobeys markovnikov rule, but Cl and I are not effected,

Normally Br follows markovnikov, but when it is with ROOR it follows anit-markovnikov rules.

Does this mean Br and Cl follows markovnikov rules normally . But when Br is in ROOR it follows anti-markovnikov rules and Cl is never affected either way it will always follow markovnikov rules