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Distinguishing between the products A, B and C is quite challenging by IR spectr

ID: 935295 • Letter: D

Question

Distinguishing between the products A, B and C is quite challenging by IR spectroscopy alone - explain the differences and similarities that you would expect to see in the corresponding IR spectra. Which functional groups are the same, and which are different?

Distinguishing between the products A, B and C is quite challenging by IR spectroscopy alone - explain the differences and similarities that you would expect to see in the corresponding IR spectra. Which functional groups are the same, and which are different?

Explanation / Answer

The best way to distinguish the given compounds is UV-Visible technique.

However we wish to distinguish these on the basis of IR spectra so:

1. A and B will be different form C in having stretching vibration of C=C-H bond near 3000-3100cm-1, =C-H out of plane bending: 1000 - 650 cm-1 due to dobule bond.

2. A and B can be distinguished from the substitutiion pattern on alkene

In A the alkene is disubstituted only so it will give IR spectra near 880-900 ( geminal disbustitued) due to sp2 CH bend

In B alkene is trisubstituted so the sp2 CH bend will appear near 790-840 .

Rest the groups are similar in all the three compounds.