A bottle of allyl bromide was found to contain a large amount of an impurity. A careful

Chapter 13, Problem PROBLEM 13-29

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A bottle of allyl bromide was found to contain a large amount of an impurity. A careful distillation separated the impurity, which has the molecular formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{C}\). The following \({ }^{13} \mathrm{C} \text { NMR }\) spectrum of the impurity was obtained:

(a) Propose a structure for this impurity.

(b) Assign the peaks in the \({ }^{13} \mathrm{C} \text { NMF }\) spectrum to the carbon atoms in the structure.

(c) Suggest how this impurity arose in the allyl bromide sample.

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