[Rutherford]

I need some help here. Got that:
a=HNO₃+H2SO₄
b=Fe+H⁺
c=NaNO₂+HCl
d= I thought benzoic acid, so an ester is made, but in the answer it is benzoylchloride. Why?
I don't understand the reaction with Br₂/CH₃COOH. Why is acetic acid added and how do I know where the bromine will be substituted? Could it as an electrophile attack the carbonyl group?
That's for now.

[synthnick]

Br2/CH3COOH is the standard conditions for α-bromination of ketones.

[discodermolide]

Only when there is an alpha hydrogen present.

[Rutherford]

Thanks, didn't know that. Then B has to be C₆H₅COO-C₆H₄-COCH₂Cl
The only two things that bother me now are d and the conversion from B to C. Could someone explain these?

[discodermolide]

d looks like an esterification with benzoyl chloride.
I'll think about the other one.

[Rutherford]

Yes it is benzoyl chloride, but why couldn't it be benzoic acid? Because of poor yield, as it is a weak acid?

[discodermolide]

It is esterifying a phenol which are less reactive than normal alcohols towards estification. Then you need an acid chloride's reactivity to do this reaction.

[Rutherford]

I will write C to make it easier OH-C₆H₄-COCH₂NH₂. Now, how to rationalize the conversion from B to C?