Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following two-step reaction sequence:
Correct answer
1
Step-by-step solution
The given reaction sequence involves two steps: The starting material, an alcohol with the -OH group on a wedge, reacts with p -toluenesulfonyl chloride (TsCl) in the presence of pyridine. This reaction converts the poor leaving group (-OH) into a good leaving group, a tosylate (-OTs). Because the C-O bond is not broken during this step, the reaction proceeds with retention of configuration. Thus, the intermediate formed will have the -OTs group on a wedge. The tosylate intermediate is then treated with sodium cyan