nitration of p-nitrobromobenzene

[hellomister]

Hi guys,

 

I was wondering if a second nitration of p-nitrobromobenzene would work using a catalytic amount of H2SO4. I was thinking it wouldn't since both the bromine and the Nitro group are deactivating substituents, and since its a catalytic amount of acid it wouldnt add a second nitro group onto the ring. Is this reasoning correct?

[nitric]

As far i see it it makes sense, but they have made trinitrotoluene which has three deactivating groups and had to get through from DNT, they used heating to about 70-80*C to do that nitration. The group would add to the meta position since its being deactivated.

[hermanntrude]

do NOT try this at home. trinitrotoluene is TNT which of course is a dangerous explosive.

 

Anyone who HAS tried this at home and would like to tell us all about it, please shut up.

[UC]

Hi guys,

 

I was wondering if a second nitration of p-nitrobromobenzene would work using a catalytic amount of H2SO4. I was thinking it wouldn't since both the bromine and the Nitro group are deactivating substituents, and since its a catalytic amount of acid it wouldnt add a second nitro group onto the ring. Is this reasoning correct?

 

No, there is a reason nitrating mixtures for polynitrated benzene rings contain a vast amount of concentrated or fuming H2SO4. The ring is extremely deactivated, especially in this case. Any chance or reaction would require a high concentration of nitronium ion, and probably a fair amount of heat.