Cyclohexyl bromide (3) can be prepared from cyclohexanol (4) byreaction with sodium bromide in the presence of an acid catalysts. In one such preparation,water (20 mL), sodium bromide (20 g) and cyclohexanol (10.5 mL, density 0.96) were mixed andconcentrated sulfuric acid (20 mL; density 1.85) was added dropwise to the swirled solution overabout two minutes. The mixture was heated under reflux for five minutes, then distilleduntil no more water-insoluble droplets came over. The distillate was washed with water (10 mL),ice-cold concentrated sulfuric acid (10 mL), 10% sodium hydroxide solution (10 mL, density 1.0),and water (10 mL). Calcium chloride was added to the product. After filtration, the liquid wasdistilled and the fraction boiling between 155 and 165∞C was collected. The yield was 8.1 g.
- What is the theoretical yield of cyclohexyl bromide from thequantities of reagents used?
- What is the percentage yield of cyclohexyl bromide?