The 1H NMR for a dipeptide recorded in D20 is shown below. (i) Explain what has happened to the H- atoms attached to the N atoms.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins
Section26.SE: Something Extra
Problem 28MP
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The 1H NMR for a dipeptide recorded in D20
is shown below.
(i) Explain what has happened to the H-
atoms attached to the N atoms.
(ii) Explain the spectra. Note the signals for HA
and HA'are subject to a second order effect.
H^H*
40 Hz
0.1 ppm
'N-
DN Ha
L-Ala-Gly
(iii) predict which direction the signal for the H
on the alpha-C will move in the 1H NMR on
going from low to high ph and explain why
this leads to a change in chemical shift.
Transcribed Image Text:The 1H NMR for a dipeptide recorded in D20 is shown below. (i) Explain what has happened to the H- atoms attached to the N atoms. (ii) Explain the spectra. Note the signals for HA and HA'are subject to a second order effect. H^H* 40 Hz 0.1 ppm 'N- DN Ha L-Ala-Gly (iii) predict which direction the signal for the H on the alpha-C will move in the 1H NMR on going from low to high ph and explain why this leads to a change in chemical shift.
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