Which is the correct sequence of reactions required to transform the starting material into the product shown?

Question

Quizplus · Accepted Answer

The product shown is a diol with two OH groups on adjacent carbons, which suggests that it was formed via syn dihydroxylation of an alkene. The reagent for syn dihydroxylation is KMnO4 in basic solution. Therefore, KMnO4 is required in the reaction sequence. The starting material is an alkene with a benzene ring, which suggests that it is an aromatic compound. It is known that aromatic compounds do not react with KMnO4. Therefore, a protecting group such as NHSO2C6H4 is needed to mask the aromatic ring during the reaction. The protecting group must be removed after the dihydroxylation to obtain the final product. NaBH4 is commonly used to reduce the intermediate manganese oxide to form the diol. Therefore, the correct sequence of reactions is KMnO4, then NaBH4/NHSO2C6H4. Among the given choices, only choice B has the correct order of reagents.

Which Is the Correct Sequence of Reactions Required to Transform