[lethal_lefty]

I was hoping that maybe someone could help me, I have a couple of synthesizing problems I have to do for my organic chem class and I'm a bit lost.  I've looked at the textbook and searched the internet but haven't found anything leading me in the right direction, hopefully someone can help me.

for the first synthesis: beginning with either benzene or toluene I need to synthesize p-bromoaminobenzene (p-bromoaniline).  here's what i have so far:  beginning with benzene I reacted it with Br₂/FeBr₃.  I don't know what the next step of this reaction should be.

for the 2nd synthesis I am completely lost.  again, beginning with benzene or toluene I need to produce p-di-t-butylbenzene.  I don't know where to begin with this synthesis.

If anyone could help me out I would deeply appreciate it.

[movies]

For the first question, I'm guessing that you haven't learned any ways to directly introduce an amino group onto an aromatic ring.  What other ways do you know to generate an NH₂?  What ways do you know that will make a N-C bond on an aromatic ring?

For the second one, you need to make a C-C bond.  I'm sure that you have learned at least one way to make a C-C bond from an aromatic ring!  What is the other component that you would need in the reaction?