The above section of an NMR was taken from a student sample of this experiment. You see while the 2H triplet is still present at around 4.3 ppm, the 2H quartet is gone, replaced by a 3H singlet. As well a 3H triplet at 1.4 ppm also is missing from the NMR. Looking at the procedure for purifying virstatin ethyl ester you see that the ethyl ester is boiled in methanol. It appears that transesterification may occur in this process, resulting in virstatin methyl ester. In light of this statement explain the 3H singlet shown above and the missing 3H triplet. You may draw structures to help in your explanation, in any case make sure the hydrogens you are discussing are UNAMBIGUOUS.

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4 A) The NMR of virstatin ethyl ester shows a deshielded triplet around 4.3 ppm and a deshielded quartet
around 4.15 ppm. On the section of virstatin ethyl ester shown below UNAMBIGUOUSLY show which
hydrogens in the molecule are giving rise to the deshielded quartet. (The deshielded triplet is from the CH2
group attached to the nitrogen).
w
- yya m
rial I vietstia athy ter
[ppm)
4B)
4.a
(ppm)
The above section of an NMR was taken from a student sample of this experiment. You see while the 2H
triplet is still present at around 4.3 ppm, the 2H quartet is gone, replaced by a 3H singlet. As well a 3H
triplet at 1.4 ppm also is missing from the NMR. Looking at the procedure for purifying virstatin ethyl ester
you see that the ethyl ester is boiled in methanol. It appears that transesterification may occur in this
process, resulting in virstatin methyl ester. In light of this statement explain the 3H singlet shown above
and the missing 3H triplet. You may draw structures to help in your explanation, in any case make sure the
hydrogens you are discussing are UNAMBIGUOUS.
Transcribed Image Text:4 A) The NMR of virstatin ethyl ester shows a deshielded triplet around 4.3 ppm and a deshielded quartet around 4.15 ppm. On the section of virstatin ethyl ester shown below UNAMBIGUOUSLY show which hydrogens in the molecule are giving rise to the deshielded quartet. (The deshielded triplet is from the CH2 group attached to the nitrogen). w - yya m rial I vietstia athy ter [ppm) 4B) 4.a (ppm) The above section of an NMR was taken from a student sample of this experiment. You see while the 2H triplet is still present at around 4.3 ppm, the 2H quartet is gone, replaced by a 3H singlet. As well a 3H triplet at 1.4 ppm also is missing from the NMR. Looking at the procedure for purifying virstatin ethyl ester you see that the ethyl ester is boiled in methanol. It appears that transesterification may occur in this process, resulting in virstatin methyl ester. In light of this statement explain the 3H singlet shown above and the missing 3H triplet. You may draw structures to help in your explanation, in any case make sure the hydrogens you are discussing are UNAMBIGUOUS.
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