Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Messi on December 04, 2012, 08:36:53 PM
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Hey guys, I have the reaction shown below.
For step d), I was wondering what type of reaction that was, so I can look up the reaction mechanism.
Also, for step e), the percent yield was only 10%. I was wondering why this was the case? Why only 10%? What happened? What are the competing reactions perhaps?
Thanks!
Edit: Also, what do the square brackets mean?
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Step d) is a nucleophilic aromatic substitution. I don't know what I was thinking!
For step e), the percent yield was only 10%. I was wondering why this was the case? Why only 10%? What happened? What are the competing reactions perhaps?
Thanks!
Edit: Also, what do the square brackets mean?
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Something went wrong in the hydrogenation step.
Are there any intermediates in the reduction of a nitro group by hydrogen which can react with amines?
A compound in square brackets usually means that it is not isolated but taken through to the next step.
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I think the 10% refers to the Pd loading on the charcoal (i.e. the Pd/C is 1:9 Pd:C).
The square brackets are usually used to indicate the product was not isolated but reacted further without purification (hence no yield reported). I think the scheme originally had a step f) that is missing, and the yield obtained over the two (or more) steps before purification would have been reported. The reagents list also ends in a semicolon, which hints that this is not the full sequence and that the rest of it has been edited out.
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Oops, just told my professor that a possibly intermediate of the above reaction was a nitrosbenzene-like group (N=O) and that reacted with the amine group adjacent to it.
I told her that was possibly the reason why the yield was only 10% :)