Question

What compounds are obtained when (+)-limonene (its structure is on page 1144) reacts with O₃followed by dimethyl sulfide?

Short answer

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene and is the major component in the oil of citrus fruit peels. It is used to make medicine. Limonene is used for obesity, cancer, and bronchitis, but there is no good scientific evidence to support these uses.

Step-by-step solution

Limonene

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene and is the major component in the oil of citrus fruit peels. It is used to make medicine. Limonene is used for obesity, cancer, and bronchitis, but there is no good scientific evidence to support these uses.

Formation of the desired product

Limonene undergoes ozonolysis in the presence of O₃, to form limonene-1,2-diepoxide which then reacts with dimethyl sulfide to form 6-oxo-3-(prop-1-en-2-yl) heptanal. The reaction is represented as follows:

Formation of the desired product