Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Consider the hydroboration-oxidation of 1-methylcyclopentene: Which of the following correctly identifies the products formed in this reaction? I. II. III. IV. V.
Options
- AAn equal mixture of II and IV
- BAn equal mixture of I and II
- CAn equal mixture of I and V
- DAn equal mixture of IV and V
Correct answer
A. An equal mixture of II and IV
Step-by-step solution
Hydroboration-oxidation of 1-methylcyclopentene results in the anti-Markovnikov, syn addition of water across the double bond. The OH group attaches to the less substituted carbon (C2), while the H atom attaches to the more substituted carbon (C1). Because the addition is syn, the incoming H and OH groups must add to the same face of the double bond. If addition occurs from the top face, the added H and OH are on wedges. The original CH ₃ at C1 and H at C2 are pushed to dashes. This yields structure IV, which is a