Lab summary

  In the lab, 0.064 g sodium hydroxide and 0.200g 2-naphthol  were added to a flask. 3mL ethanol was then added to the flask. Then the solution was refluxed for 25 minutes and cooled for 3 minutes. 0.2mL N-butyl iodide was added to the solution and the solution was refluxed for one hour. Around the 10 minute left point in the reflux, 25 mL water was cooled in an ice bath. The reaction mixture was poured over 10 g of ice in a beaker and stirred until 95% of the ice had melted. The product was then collected via suction filtration. The product was rinsed with ice-cold water and dried under suction for 25 minutes. The melting point of the product was then taken. To analyze the polarity of the product, thin layer chromatography (TLC) was performed. A small amount of product was dissolved in ethyl acetate and a small amount of 2-naphthol was also dissolved in ethyl acetate. Then three TLC plates were prepared with three spots A, B and C from left to right (A was the 2-naphthol solution, B was 50% 2-naphthol solution and 50% product solution, and C was the product solution). One plate was run in 75:25 hexanes:EtOAc solution; one plate was run in 25:75 hexanes:EtOAc solution; and the third plate was run in 60:40 hexanes:EtOAc solution.