Question

If you conducted this experiment using (R) 2-bromobutane, what would be the stereochemistry of the product? How, if at all, would the stereochemistry of the product differ if the sodium iodide had not been included in the reaction mixture?

This is the experiment:

Formation of n-Butyl Acetate Just Below Reflux

1. Set up a sand bath on a magnetic stirrer— start on “4” until it reaches 100°C
2. To a 5-mL long-necked round-bottomed flask, add 0.750 g of sodium acetate trihydrate (NaOAc • 3H₂O), 0.500 g of 1-bromobutane, 0.05 g of sodium iodide (NaI, spatula tip amount), then add 1.5 mL of DMF
3. Gently heat the mixture at 100°C over the sand bath for 60 minutes
4. Allow the fractionating column to cool

Steam Distillation of n-Butyl Acetate

1. Remove the fractionating column from the reaction flask
2. Add 2 mL of water to the reaction mixture
3. Slowly distill the mixture while adding a few drops of water to the distillation flask once you have collected about 0.5 mL of distillate
4. Stop the distillation once the temperature reaches 100°C
5. Using a pipet, carefully transfer the top layer from the receiving vessel into a clean, dry reaction tube
6. Add 1-2 spatula tips of sodium sulfate and gently swirl
7. When the product is dry (clear, not cloudy), use a pipet to transfer the product in a clean, dry, and tared reaction tube
8. Weigh the tube containing your product
9. Record an IR spectrum

Answer 1