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