The two nitrogen hydrogens in Dilantin are not equivalent. Ha is an imide hydrog

Question

The two nitrogen hydrogens in Dilantin are not equivalent. Ha is an imide hydrogen and Hb is an amide hydrogen. 4. Which is more acidic, Ha or Hb? Look up approximate pKa values for amides and imides to justify your answer. In the HNMR spectrum of Dilantin, Hb appears as a broad singlet near 11 ppm and Ha appears as a sharp singlet at 9.4 ppm. Consider the chemical properties of Ha and Hb Explain the difference in chemical shift and the difference in appearance in the HNMR spectrum a. b. 2 14 12 10

Explanation / Answer

a.) In the above molecule Ha is more acidic because the negative generated on N after picking the proton by base is resonance stablised between two carbonyl group.

b) In terms of chemical properties Ha is more acidic, since the acidity of the protons is different which is the valid reason for their different chemical shift values and their appearence ih 1HNMR

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