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Organic Chemistry 1

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Using NMR Spectrum of Products to Interpret Reactions 4

ORGO1-E8PFUU

Identify the reaction conditions that would give a product most consistent with the $^1H$ NMR peaks provided. All of the spectra were obtained in $CDCl_3$.

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

$^1$H NMR peaks for product
3.70 ppm (doublet of quartets, J=10.4 and 6.4 Hz, 1H)
2.01 ppm (doublet of septets, J=10.4 and 6.8 Hz, 1H)
1.71 ppm (doublet, J=6.4 Hz, 3H)
0.88 ppm (doublet, J=6.8 Hz, 6H)

A

$HBr$

B

$HBr, \text{peroxides}$

C

$Br_2, CH_2Cl_2$

D

$Br_2, H_2O$