Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Which one of the following is the major product of the given reaction?
Correct answer
3
Step-by-step solution
The reaction involves an intramolecular Williamson ether synthesis. The strong base NaH deprotonates the hydroxyl group to form a nucleophilic alkoxide ion. This alkoxide undergoes an intramolecular S_N2 reaction, attacking the carbon atom bearing the bromine leaving group to form a fused six-membered ring. In the starting chair conformation, the bromine atom is on an upward-pointing carbon and its bond is straight up, indicating an axial position. Thus, it is an up substituent. The 3-hydroxypropyl chain is on the