Bromination of 3-methyl-2-butanone yielded two compounds, each having the molecular formula C5H9BrO,...

Question

Bromination of 3-methyl-2-butanone yielded two compounds, each having the molecular formula C5H9BrO, in a 95:5 ratio. The 1H NMR spectrum of the major isomer A was characterized by a doublet at d 1.2 ppm (6 protons), a septet at d 3.0 ppm (1 proton), and a singlet at d 4.1 ppm (2 protons). The 1H NMR spectrum of the minor isomer B exhibited two singlets, one at d 1.9 ppm and the other at d 2.5 ppm. The lower field singlet had half the area of the higher field one. Suggest reasonable structures for these two compounds.

David · Accepted Answer

O O
O
bromination Br
+
Br
Major
Isomer-A
Minor
Isomer-B
 4.1 ppm, 
singlet, 2 H 1.2 ppm, doublet
6 H
 3.0 ppm,
septet, 1 H
 1.9 ppm, 
singlet, 6 H
 2.5 ppm, 
singlet, 3 H

Bromination of 3-methyl-2-butanone yielded two compounds, each having the molecular formula C5H9BrO, in a 95:5 ratio. The 1H NMR spectrum of the major isomer A was characterized by a doublet at d 1.2...

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