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Chapter 18: Question 18.43 (page 967)

A compound of formula C6H10O2 shows only two absorptions in proton NMR: a singlet at 2.67 ppm and singlet at 2.15 ppm. These absorptions have areas in the ratio 2:3. The IR spectrum shows strong absorption at 1708 cm-1. Propose structure of compound.

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01

Information from IR frequency

Given that theIR spectrum shows strong absorption at 1708 cm-1. This means there is a carbonyl (-CO-) group present in the molecule.

02

Information from proton NMR

It is also given that there are only two types of hydrogen that are present and are in a ratio of 2:3. The above structure satisfies this condition as only two types of hydrogen are present and are in a ratio of 2:3. Alsotwo absorptions in proton NMR: a singlet at 2.67 ppm (due to CH3) and singlet at 2.15 ppm (due to CH2) is observed in the above molecule.

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