Which of the following would allow you to distinguish the two compounds shown (1

Question

Which of the following would allow you to distinguish the two compounds shown (1 and 2), if you were given the 1H NMR spectrum for each? There are TWO possible correct answers- pick either one of them.

a) 1 would have a smaller integration than 2
b) 1 would have a triplet at around 4ppm, whereas 2 would have its most downfield triplet at 2.2 ppm
c) 2 would have four types of H, whereas 1 would have five types.
d) In 1, the CH3 groups would show triplets, whereas in 2 they would show as singlets.
e) 1 would gave its only singlet at 3.8 ppm, whereas 2 would have its only singlet at 2 ppm
f) 1 would have its only singlet at 2ppm, whereas 2 would have its only singley at 3.7 ppm

Explanation / Answer

Ketonic methyl group are less deshielded than ester methyl (COOMe). Both will give singlet because the do not have any proton on neighbouring carbon.

So, the correct answer will be answer (f).

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