19. (2 points) Upon nitration of aniline with HNO /So, a very poor yield (if any

Question

19. (2 points) Upon nitration of aniline with HNO /So, a very poor yield (if any) of meta-nitro aniline is formed why such a poor yield and why meta-subsitution occurs instead of ortho-/para- 20. (5 pts) From the following information, identify this unknown compound C3HeO and draw its structure. BP 46: soluble in water, gives positive 2,4-DNP and Tollen's tests. Identify the pertinent IR absorptions on the IR spectrum, and indicate the type of Hs for each resonance on the 'H-NMR spectrum and the Cs in the C-NMR spectrum. 13C NMR Spectrum proton coupled 200 160 120 80 40 0 8(ppm)

Explanation / Answer

19.) when aniline is nitrated with HNO3/H2SO4 solution then under such acidic conditions protonation of the free amine takes place resulting in the formation of ammonium ion. This ammonium ion is incapable of donating electrons to the benzene ring to participate in the resonance making it into polar electron withdrawing group which is a meta director and hence formation of meta-nitroaniline. Secondly, the yield of this nitration is poor since free amine group is susceptible to oxidation which converts the majority of aniline into the tarry material.

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