[lespan]

Hi, I need help for this: p-nitrophenol reacts with 2-chloropropanoic acid and produces a compound 1. 1 reacts with thionyl chloride and produces a compound 2. 2 reacts with ethylene glycol and produces a compound 3. 3 reacts with methyl isocyanate and produces a compound 4. No reaction conditions are indicated explictly.
Firstly, I think that the first reaction produces an ester but the second step with thionyl chloride is pointless. Maybe the first reaction is a nucleophilic substitution? p-nitrophenoxide with carbon 2 of the chloropropanoic acid? And the next steps?

Thanks a lot.

[discodermolide]

I replied to this over at Science Forums, have a look there

[lespan]

Thanks but it's all what my teacher said to solve the exercise. I need suggestions!

[discodermolide]

Well following the reaction sequence you describe I would not apply it to an ester. So have a re-think about the first step.

[lespan]

I think the first step will produces a 2-(p-nitrophenoxy)-propionate. It is right?

[discodermolide]

No, I don't think so.
Look at the next step, will your ester react with thionyl chloride?
What usually reacts with thionyl chloride?

[lespan]

My conjecture is this:



Is correct?

Thanks in advance!

[discodermolide]

Yes, that looks better to me and fits with the reagents you describe.

[lespan]

Thanks!