Question

Draw a structure for the compound, C3H5Br, that fits the following 1H NMR data:\ δ 2.32...

Draw a structure for the compound, C3H5Br, that fits the following 1H NMR data:\

δ 2.32 (3H, singlet)

δ 5.35 (1H, broad singlet)

δ 5.54 (1H, broad singlet)

Science   Chemistry   
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Answer #1

We need to analyze the shifts first:

  • The shift at 2.32 represents a -CH3 group bonded to a C-Br fragment.
  • The shifts at 5.35 and 5.54 are so close to each other and since they are singlets we can say they belong to a vinylic alkene (further down is the explanation on why the protons of a vinyl alkene aren't equal and why their signals aren't produced as one).

The compound is 2-bromopropene.

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