[spyder45]

Hi, I have two questions for an assignment with my own answers, but I am not sure if they are correct. If anyone can provide feedback on the questions, so I would know if I did them right or wrong before handing them in. Thank you.

[nj_bartel]

For the first one, I believe you nitrated in the wrong position.  Also, I'm not sure why you have 2+'s on your amides (assuming that is acetic anhydride and i'm not misreading it)

[spyder45]

Yes for the first one I was not fully sure in which position I would nitrate it because of the cyclichexane attached to the benzene ring. I assumed that the cyclic ring is more activating then the -NO2 group on the benzene, and thus would favour the positions relative to the cyclic ring. I also assumed it would be either ortho or para directing since they are activators and the ketone is far away from the benzene ring preventing it from withdrawing electrons. If we do ortho and para, the only position in which the -NO2 group can be added is in the position I put it. But I am not sure.

Also for the Ac+2 question, I meant to put only Ac which is attached to the Nitrogen. Is the way I did this correct? My professor did not use this reagent in lectures and it is not in the textbook.

[aldoxime_amine]

In reaction 2, wouldn't the KMnO4 cleave off both alkyl side chains (propyl and methyl) ?
Also SOCl2 ( 1 eq ) will give mixture of products, as it may chlorinate either of the 2 resulting carboxyl groups.

I wonder why NBS is used?

[spyder45]

In reaction 2, there is only 1 eq of KMnO4 so it would only cleave off the CH3 since more hydrogens present. But can anyone please tell me if the position I placed my methyl group is correct. Or does it go beside the propyl group on the main benzene ring since it is more activating. Thank you.