Organic Chemistry

 

Compound W is a hydrocarbon with MW 124. The 13C NMR spectrum of W consists of 5 peaks and one of these appears above 80 ppm. One mole of W reacts with just one mole of hydrogen gas in the presence of Pt catalyst. When W is subjected to ozonolysis, just one compound, Y, is formed. Compound Y has MW 156 and combustion analysis of Y shows %C, 69.2 and %H, 10.3. Y reacts with 2,4-DNP but not with Fehlings or Tollens reagents. The IR spectrum of Y contains a strong band at 1690cm-1 but no bands at 1600cm-1 or above 3100cm-1. The 13C NMR spectrum of Y contains five peaks and only one of these appears at higher than 80 ppm. The 1H NMR spectrum of Y consists of three sets of peaks with an area ratio of 3:2:3.

Deduce the structure of W and Y showing all your reasoning.

 

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