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A bottle of allyl bromide was found to contain a large

Chapter 18, Problem 29P

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QUESTION:

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 \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\). The following \({ }^{13} \mathrm{C} \mathrm{NMR}\) spectrum of the impurity was obtained:

(a) Propose a structure for this impurity.

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

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

Equation Transcription:

Text Transcription:

C_{3}H_{6}O

^{13}C NMR

C_{3}H_{6}O

delta(ppm)

^{13}C NMR

Questions & Answers

QUESTION:

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 \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\). The following \({ }^{13} \mathrm{C} \mathrm{NMR}\) spectrum of the impurity was obtained:

(a) Propose a structure for this impurity.

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

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

Equation Transcription:

Text Transcription:

C_{3}H_{6}O

^{13}C NMR

C_{3}H_{6}O

delta(ppm)

^{13}C NMR

ANSWER:

Solution 29P

(a)

So from the above data the structure of the compound is:

        

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