Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide.

Question

Quizplus · Accepted Answer

The reaction sequence involves the conversion of an alcohol to a good leaving group using TsCl (tosyl chloride) in the presence of pyridine, followed by a nucleophilic substitution with sodium bromide. The tosylate formed from cis-3-methylcyclopentanol will undergo an SN2 reaction with sodium bromide, leading to inversion of configuration at the carbon that was originally bearing the hydroxyl group. This results in the formation of trans-1-bromo-3-methylcyclopentane.

Predict the Product When Cis-3-Methylcyclopentanol Is Treated with TsCl/pyridine, Followed