Hi, I recently performed a reaction involving an organic base in Ethyl Acetate. After extracting the final product I added hydrochloric acid solution and water (producing the hydrochloride salt), but far too much acid making the solution extremely acidic. It was like this for a period of days until I evaporated off the water and was left with approximately 100g of yellow/white crystals (70% yield). At this point the product was tested and tested negative.
Is it possible I've damaged the molecule with the high acid concentration?