Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
What is the major product of the given reaction?
Correct answer
2
Step-by-step solution
Aqueous AgNO ₃ abstracts the Br ^- ion to form a primary carbocation adjacent to the cyclopentane ring. The unstable primary carbocation undergoes a semi-pinacol rearrangement. A ring expansion occurs where a C-C bond of the five-membered ring migrates to the - CH ₂^+ carbon, forming a six-membered ring. The positive charge shifts to the carbon bearing the - OH group, resulting in a resonance-stabilized oxocarbenium ion. Loss of a proton from the oxocarbenium ion gives cyclohexanone as the final major product. Answ