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1. An unknown compound shows a weak molecular ion at m/z 87 in the mass spectrum

ID: 841861 • Letter: 1

Question

1.

An unknown compound shows a weak molecular ion at m/z 87 in the mass spectrum, and the only large peak is at m/z 30. The IR spectrum appears below. The NMR spectrum shows only three singlets: one of area 9 at 0.9 ppm, one of area 2 at 1.0 ppm, and one of area 2 at 2.4 ppm. The singlet at 1.0 ppm disappears on shaking with D2O.

Draw the structure of the major fragment with m/z 30.

2.

3.

Identify the compound with molecular formula C4H7ClO that gives the following IR and 1H NMR spectra.

Propose a structure consistent with the following NMR spectra and this additional information. The mass spectrum shows a double molecular ion of ratio 1:1 at m/z 184 and 186.

Explanation / Answer

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