Question

Compound A was isolated from Rose oil. The molecular formula was determined by elemental analysis to be C10H18O. Compound A does not form any derivatives with 2,4-dinitrophenylhydrazine or hydroxylamine. Compound A does react with sodium and releases hydrogen quite slowly. It does not react under oxidative conditions but when treated with acid isomerizes to compound B. Compound B oxidizes to an aldehyde (Compound C) when treated with MnO2. Compound A gives Laevulinic acid (CH3COCH2CH2COOH), acetone and CO2 when reacted with O3 under oxidation conditions. Hydrogenation of compound A gives Compound D (C10H22O). Compound D reacts with acid to give two isomeric alkene products, Compound E and Compound F. Compound E gives acetic acid and 2-methylheptan-6-one when treated with ozone under oxidative conditions. What are the structures of Compounds A-F? Show how you arrived at these conclusions and explain how the isoprene rule might help with structure determination.

Answer 1