Chemistry 29b

Practice NMR Spectral Problem C

Spectrum C:

The splitting and the integration of the three multiplets strongly suggest an n-propyl group attached to a strongly electronegative group such as O (too downfield for Br, and anyway 1-bromopropane wouldn’t have enough for the formula).  We have only one DBE, and the 13C NMR strongly suggests that we have an ester present.  We have a CH2Br left over, giving the structure shown.  Note that if the CH2Br were directly attached to the O of the ester, it would be at around 5 ppm, and the end CH2 of the propyl would be only at around 2.3 ppm, so we can rule out the isomer, bromomethyl butanoate.

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