1. The ¹H-NMR of the product shows signals (two doublets) in thearomatic region and a very broad signal (the signal is almost flatfrom ~5.0 ppm to -6.5 ppm and may actually extend into the Hdoublet at ~ 6.7 ppm) which may indicate a "combination" of theamine and acid peaks. (The small peak at ~ 2 ppm should beignored.)H"HAHdabC a.b.C.The amine group can be considered to be electron donating toward the ring by resonance, thus itwill place a partial negative charge on the (relative) ortho and para positions. Draw threeresonance structures for the product, showing the resulting charges at these positions. Will thisresonance effect lead to shielding or deshielding for the protons labelled as Hb compared to Hc?Based on your answer, which of the protons (Hb or Hc) should be at larger chemical shift (lowerfield)? Explain briefly.The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place apartial positive charge on the (relative) ortho and para positions. Draw three resonancestructures for the product, showing the resulting charges at these positions. Will this resonanceeffect lead to shielding or deshielding for the protons labelled as Hc compared to Hb? Based onyour answer, which of the protons (Hb or Hc) should be at larger chemical shift (lower field)?Explain briefly.After the previous two parts of this question have been completed, fill in the table on theprevious page. Note that you should be able to predict how the spectrum should appear, butyou will not see the expected peaks for some of the signals. If the spectrum does not clearlyshow the some of the signals, you write "inconclusive" in the table cells for those observations.

1H-NMR is used for to know the complete structure of the unknown compound. It is gives the…

The 'H-NMR of the product shows signals (two doublets) in the aromatic region and a very broad signal (the signal is almost flat from -5.0 ppm to -6.5 ppm and may actually extend into the H doublet at ~ 6.7 ppm) which may indicate a "combination" of the amine and acid peaks. (The small peak at 2 ppm should be ignored.) H d b

The 'H-NMR of the product shows signals (two doublets) in the aromatic region and a very broad signal (the signal is almost flat from -5.0 ppm to -6.5 ppm and may actually extend into the H doublet at ~ 6.7 ppm) which may indicate a "combination" of the amine and acid peaks. (The small peak at 2 ppm should be ignored.) H d b

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 3E

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