Question

The target diol is synthesized in one step from 1-methylcyclopentene, but your lab partner exhausted the supply of that alkene. Fortunately, you have plenty of isomers (C6H10) on hand from which to synthesize 1-methylcyclopentene and, ultimately, the diol. Provide the missing reagents and organic structures needed to most efficiently produce the target product.

Answer 1

Answer:

The reagents are $CH_{3}CH_{3}O^{-},OsO_{4},NaHSO_{3}and H_{2}O$.

Explanation:

1-Methylenecyclopentene is treated with HBr form 1-bromo-1-methylcyclopentane, which is treated with strong base ethoxide ion and forms 1-methylcyclopent-1-ene.

This alkene is treated with osmium tetraoxide in the presence of sodium bisulfite to form target product.

The chemical reaction is as follows.