Compound A (C8H16) decolorized a bromine–methylene chloride solution. Ozonolysis produced two compounds, B and C, which could be separated easily by gas chromatography. Both B and C gave a positive 2,4 dinitrophenylhydrazine test. Carbon–hydrogen analysis and molecular weight determination of B gave a molecular formula of C5H10O.The H NMR spectrum revealed the following information for B:

0.92 ppm           3H, triplet                    2.17 ppm            3H, singlet

1.6 ppm             2H, pentet                   2.45 ppm            2H, triplet

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

 

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