Solution: Hydrocarbon (A), C9H16, is chiral, possess a ring of five carbon atoms, contains four methyl groups, and absorbs one equivalent of H2 upon treatment with H2 over nickel catalyst to yield a racemic hydrocarbon, C9H18. When hydrocarbon (A) is treated with peracetic acid (CH3COOOH) and then with CH3MgBr, the major product (after exposure to dilute acid) is a teriary alcohol (B). (B) is not chiral. What is the structure of (A) and (B)?

Problem

Hydrocarbon (A), C9H16, is chiral, possess a ring of five carbon atoms, contains four methyl groups, and absorbs one equivalent of H2 upon treatment with H2 over nickel catalyst to yield a racemic hydrocarbon, C9H18. When hydrocarbon (A) is treated with peracetic acid (CH3COOOH) and then with CH3MgBr, the major product (after exposure to dilute acid) is a teriary alcohol (B). (B) is not chiral. What is the structure of (A) and (B)?