Chemistry 29b

Practice NMR Spectral Problem B

Spectrum B:

Two DBEs.  The 1H singlet at 9.5 and the 13C peak at 207 ppm strongly indicate an aldehyde with no alpha proton.  The three signals in the 5-6 ppm range, in combination with the 13C peaks at 118 and 134 ppm, suggest a monosubstituted alkene.  What do we have left over?  A CH3 singlet that integrates to 6H, indicating C–C(CH3)2-C or similar, and also a CH2 doublet that is split by a neighboring alkene C-H.

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