Question
Can you correspond each of the peaks to the protons in one of the following molecules? Also, does the spectrum correspond to the Z or E alkene?

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3.5 3.0 2.0 1.5 Ppa 3.00
ISOS 7.230 0669 7.8 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 ppm
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Answer #1

6 1 2 2 4 3 3 4

- Singlet at 2.3 ppm corresponds to 3 protons of -CH3

- Singlet at 3.8 ppm corresponds to 3 protons of -OCH3

- There are four doublets at 8.1, 7.8, 7.2 and 7.0 and a multiplet at 7.5-7.6

- The first doublet at 8.1 for two protons corresponds to H1 and H4, as they are near to ketone group which is electron withdrawing and hence the signal goes downfield (J = 8.8 Hz)

- The next doublet at 7.8 for 1 proton corresponds to H5 (J = 15.6 Hz)

- The two doublets at 7.2 (J = 7.6 Hz) and 7.0 (J = 8.4 Hz) for two protons each corresponds to H1' - H3' and H2 '- H4'

- The multiplet at 7.5 is actually a mixture of two doublets, one doublet with chemical shifts at 7.552 and 7.530 for two protons (J = 8.8 Hz) corresponds to H2 and H3, the other doublet with shift value of 7.530 and 7.489 (J = 16 Hz) for one proton corresponds to H6.

- Here, the J value corresponding to H5 and H6 is in the range of 15-16 Hz, which indicates that the alkene exists as E isomer, because in Z form the J value exists around 7 Hz.

Note: Because the NMR operating frequency was not provided, the value was assumed as 400 MHz and accordingly the J value was calculated (J = difference in chemical shift of a doublet * 400)

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