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A compound C5H8O has a strong IR absorption at 1700 cm-1 and the NMR 1.4 doublet...

A compound C5H8O has a strong IR absorption at 1700 cm-1 and the NMR 1.4 doublet (3H), 1.6 multiplet (1H), 1.9 doublet (4H)

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The IR absorption at 1700 cm-1 suggests that the compound contains a carbonyl group (C=O) and the NMR peaks suggests the structure of the compound is as follows

CH3e

1. The four chemically equivalent Ha protons become deshielde due to presence of adjacent carbonyl group (-I effect) and show higher chemical shift. This protons come at 1.9 ppm as a doublet due coupling with one adjacent Hb proton (n+1) rule.

2. NMR peak at 1.6 ppm corresponds to the Hb proton, and it comes as multiplet due to coupling 7 adjacent protons (4 Ha & 3 Hb ).

3. Since the three Hc protons are far apart from the carbonyl group hence they come at comparatively lower chemical shift 1.4 ppm. Doublet nature of the peak die to coupling with the adjacent Hb proton.

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