How to Approach Challenging Organic Chemistry II Problems?

[Intr3pid]

Homework Statement

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Homework Equations

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The Attempt at a Solution

I have no idea how to attempt this problem set. The instructor had this insane idea that if he gave us questions that we've never seen/dealt with before that he'd be doing a better job. problem is that nobody knows how to attempt these questions. I'm not trying to get anyone to do my problems for me, but can u guys give me hints on how to attempt each question? I'm really puzzled and lost.

thank you for your help

 

[chemisttree]

1) What is the product formed when the protein is reacted with the 2,4-dinitrofluorobenzene? What would happen if that product were hydrolyzed with HCl? What would you see? There is a slight error in the problem. The individual amino acids shown after hydrolysis show the group HN- instead of the correct H2N- funtionality.

2) Approach this problem by doing a retrosynthetic analysis. What do you think the last reaction was to form this product? What were the reactants for that transformation and how were they formed?

3) Again do a retrosynthetic analysis. The product has the same number of carbons as the starting material but no double bond and two hydroxyls. What transformation(s) do you know that convert double bonds to diols? What process(es) will cause the scission of the carbon bond and produce diols?

4) Do you understand the reagents employed? (PCC, DMS, O3, CF3CO3H, etc...)