Help with questions

[chhay]

I need help coming up with an explanation for these. I am lost.

 

1. Nitration of aniline with a mixture of concentrated nitric acid and concentrated sulfuric acid produces mostly m-nitroaniline. Why?

 

2. How does the basicity of the nitrogen atom of acetanilide compare with that for aniline?

[CaptainPanic]

Sounds like a homework question to me... so therefore the forum policy says you don't get a complete answer, but first some hints to get you going.

 

The keyword that you may or may not know is "resonance structure". The aromatic ring in Aniline and the NH2 group interact, and electrons move around a bit, creating (mostly) positive charges on the ring and on the side groups. With this keyword you would probably find the following link anyway, so I might as well give it here: http://en.wikipedia.org/wiki/Electrophilic_aromatic_substitution

 

Remember that nitric acid is H+ and NO3-.

 

About question 2:

It is again about resonance structures (strengthening my feeling that we are in fact looking at two homework questions). Read the wiki a bit, and also check your textbook which you most likely have.

 

The real question is: how stable is the aniline and the acetaniline once the additional hydrogen is attached (making it in fact an acid).

[chhay]

Thanks for the help. Just to ease your mind it wasn't for homework help, they were those questions "thought questions" at the end of my lab, and I was just curious because I couldn't figure it out. Thanks though, your posting did help me.

[CaptainPanic]

Glad to be able to help. There is no need to ease my mind, there is even have a special section for homework help... Asking for help with homework is a very good idea.

 

It's a pity that it is kinda tricky to add chemical formula's (the structural formula's especially) here...