In a laboratory a bottle was found containing a clear liquid A. The bottle was labeled, “C₁₀H₁₆, Isolated from a lemon.” Because of your skills in organic chemistry, you have been hired to identify this substance. Compound A decolorizes Br₂ in CH₂Cl₂. When A is hydrogenated over a catalyst, two equivalents of H₂ are consumed and the product is found to be 1-isopropyl-4-methylcyclohexane. Ozonolysis of A followed by treatment of the reaction mixture with H₂O₂ gives the following compound as a major product:

Suggest a structure for A and explain all observations.

Transcribed Image Text:

O CH3CCH₂CH₂CHCH₂-C-OH C=O CH3