Question

An optically active monoterpene (compound A) with molecular formula C₁₀H₁₈Oundergoes catalytic hydrogenation to form an optically inactive compound with the molecular formula C₁₀H₂₀O(compound B). When compound B is heated with acid, followed by reaction withand then with O₃dimethyl sulfide, one of the products obtained is 4-methyl cyclohexanone. Give possible structures for compounds A and B.

Short answer

Possible structures of compounds

Compound B give same product

Step-by-step solution

Monoterpene

Terpenes have many important biological roles. They are classified according to the number of carbons they contain. Monoterpenes are composed of two isoprene units, so they have 10 carbons.

Possible structure of compound A

An optically active monoterpene compound A with molecular formula C₁₀H₁₈Oundergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C₁₀H₂₀Ocompound

Possible structures of compounds

Possible structure for compound B

Possible structures of compounds

Since, both the isomers of compound B give same product when it is heated with an acid.

Compound B give same product

When this compound is reacted with ozone followed by dimethyl sulfide then 4-methylcyclohexanone and propan-2-one is formed.

Formation of the desired product

Thus, there are five possible structures for compound A and two possible structures for compound B