Question

HCl is added to t-pentyl alcohol in a vial to synthesize t-pentyl chloride. t-pentyl chloride separates on top and the bottom layer is discarded. Sodium bicarbonate is then used to wash the crude t-pentyl chloride. What is the purpose of this wash and why would it be bad to wash with sodium hydroxide?

Answer 1

The NaHCO3 wash is to remove the excess HCl that was added initially. Would washing with NaOH reform the alcohol?

Answer 2

NaOH is a strong base, so it would likely act as a nucleophile and attack the halide making it undergo an elimination reaction, forming an undesired compound.