Identify the major product formed upon the hydroboration-oxidation of 1-methylcyclopentene.

Step-by-step solution

Hydroboration-oxidation of an alkene results in the anti-Markovnikov addition of water across the double bond. In 1-methylcyclopentene, the double bond is between C1 (bearing the methyl group) and C2. According to anti-Markovnikov's rule, the OH group attaches to the less sterically hindered, less substituted carbon (C2), and the H atom attaches to the more substituted carbon (C1). The reaction proceeds via a syn-addition mechanism, meaning the H atom and the OH group add to the same face of the double bond. Since