DAT Destroyer Baby Roadmap

[Strag]

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On page 114 of 2011.

It's NO2 attached to benzene with a Cl (meta to the NO2).

(CH3)2CuLi/ether creates a NO2 benzene with a CH3 where the Cl was...

Sorry for not having a picture, but hopefully you can visualize it.

But I thought this cannot work because Cl is attached to a sp2 carbon on the benzene ring, so it can't leave?

Shouldn't there be a no reaction?

 

[bharat008]

On page 114 of 2011.

It's NO2 attached to benzene with a Cl (meta to the NO2).

(CH3)2CuLi/ether creates a NO2 benzene with a CH3 where the Cl was...

Sorry for not having a picture, but hopefully you can visualize it.

But I thought this cannot work because Cl is attached to a sp2 carbon on the benzene ring, so it can't leave?

Shouldn't there be a no reaction?

good question.

You can't have SN1, E1, E2, SN2 rxns if you have a sp2 carbon. Benzene is usually involved with NAS and EAS rxns.
In this question, Cl is replaced with CH3 right?? If that's the case then it must be a Nucleophilic Aromatic Substitution..

Just a guess.. not sure.. Anyone else wanna explain this??

Look at this link..
http://en.wikipedia.org/wiki/Nucleophilic_aromatic_substitution

 

[herkulease]

it is done via gilman reagent.

 

[Strag]

it is done via gilman reagent.

Right. But can you do a Gilman reagent on a group that is attached to an sp2 carbon?

 

[herkulease]

Right. But can you do a Gilman reagent on a group that is attached to an sp2 carbon?

Yes. If you have McMurry's Organic Chemistry its even one of the examples of how it can be used.