[Rutherford]

I need to determine G. How will E react with 2TsCl? I thought the -OH hydrogen will be replaced by Ts, and the -NH, too. But what then? Will DMAP react?

[discodermolide]

DMAP is a catalyst, forms an intermediate with the TsCl.
Both OH and NH are tosylated.

[discodermolide]

Look here.
http://en.wikipedia.org/wiki/4-Dimethylaminopyridine

[Rutherford]

I can't solve it. What ester should be made?

[Rutherford]

What is the reaction with phenol? Is it an electrophilic aromatic substitution in the para position of phenol, where the -OTs group will be replaced with phenol?

[discodermolide]

How about the phenol displacing the OTs to give an ether as the product?

[Rutherford]

It is possible, too, but why would the ether be the main product?

[discodermolide]

Why not? It is simple alkylation of a phenol.
Please draw the product you think it is.

[discodermolide]

Just IMAGINE that instead of an OH you have a Br, how would phenol react with that?

[Rutherford]

Okay, the base will deprotonate phenol and activate it that way. That's what I oversaw. Thank you very much for the help. I really appreciate it.

[discodermolide]

No problem.
Note that very occasionally when I made a tosylate and tried to displace it with a nucleophile the reaction didn't work. What happened was that the chloride from triethylamine hydrochloride had already done the job. This happened only with certain compounds, but you should be aware that this side reaction can take place. I avoided this side reaction by using a different base.