Exo And Endo-Norborneol Reaction Lab Report

In the Acid-Catalyzed Hydration of norbornene, water and sulfuric acid were added to the C=C double bond to form norborneol. Sulfuric acid acted as a catalyst, where it was not consumed in the reaction and helped to propel the reaction forward, as it was vital in forming hydronium ion and breaking the double bond. Both the products endo-norborneol and exo-norborneol were synthesized; however regioselectivity and stereoselectivity played a role as to which product was more preferred and whether the equatorial or axial orientation of the hydroxy group was favored.The setup of the Cold-Finger, and the ability of norborneol to sublime readily allowed for the purification of the crude product to obtain the diastereomeric products exo- and endo-norborneol. …show more content…
The neutralization of the reaction was verified using pH paper to test whether the pH was neutral or slightly basic. At this point, the two possible products in the round bottom flask could have been exo- and endo-norborneol. Extraction and washing was performed and the exo- and endo-norborneol products formed were extracted into dichloromethane due to their similar solubilities, where the two products are overwhelmingly non-polar despite the one hydroxyl group. The dichloromethane (DCM) was the bottom layer formed, while the aqueous layer, the layer that was washed away, was the top and this was due to the weight of the chlorine atom that made DCM more dense. Extraction was repeated several times due to the partition coefficient, as it theorizes how smaller extractions are better than bigger extractions because they yield more concentrated extractions in the end. From there, anhydrous sodium sulfate was used to pull any remaining water left and gravity filtration was performed to filter out the anhydrous product. The dichloromethane was then transferred and evaporated in a filter flask using a vacuum and it was done over low heat as to not evaporate any important things in the crude