5064

An acyclic monoterpene, C₁₀H₁₆, consumes three moles of hydrogen upon catalytic hydrogenation. Ozonolysis of the original monoterpene, using reductive workup conditions gives the four fragments shown below in similar amounts. Suggest a structure for the terpene.

5192

Compound D has the formula C₇H₁₄O. Dehydration yields compound E. This compound reacts with HCl to yield compound F, C₇H₁₃Cl. Compound F reacts with potassium butoxide to give compound E and G; both of these compounds (E and G) have the formula C₇H₁₂. Ozonization of compound E following by Zn/H₂O work up gave cyclohexanone and formaldehyde. When compound G was treated in the same manner, 6-ketoheptanal was formed. Give structures for compounds D, E, F, and G and show equations for each transformation.