A small pilot plant was adding bromine across the double

QUESTION:

A small pilot plant was adding bromine across the double bond of but-2-ene to make 2,3-dibromobutane. A controller malfunction allowed the reaction temperature to rise beyond safe limits. A careful distillation of the product showed that several impurities had formed, including the one having the NMR spectra that appear below. Determine its structure, and assign the peaks to the protons in your structure.

Equation Transcription:

Text Transcription:

NMR

^{13}C NMR

CDCl_3

0Hz

50Hz

4.4{delta}

4.3{delta}

0Hz

50Hz

3.6{delta}

3.5{delta}

0Hz

50Hz

2.3{delta}

2.2{delta}

0Hz

50Hz

1.8{delta}

1.7{delta}

delta(ppm)