Chemistry Homework Solutions
Problem
#44721

Identifying 3 unknown compounds

Compound A (C8H16) decolorized a bromine-methylene chloride solution. Ozonolysis produced two compounds, B and C, which could be separated easily by GC. Both B and C gave a positive 2,4-dinitophenylhydrazine test. Carbon-hydrogen analysis and molecular weight determination of B gave a molecular formula of C5H10O. The 1H NMR spectrum revealed the following information for compound B:
0.92 ppm 3H (triplet)
1.60 ppm 2H (pentet)
2.17 ppm 3H (singlet)
2.45 ppm 2H (triplet)

Compound C was a low-boiling liquid (bp 56 degrees C). The 1H NMR of this material showed only one singlet.
Identify the names and structures of compounds A, B, and C

Solution
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