Acid Catalyzed Hydration Of Norbornene And Breaking The Double Bond

1629 Words Nov 11th, 2016 7 Pages
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. Because the products were diastereomers, their physical properties differed and a melting point could be obtained. The melting point was verification of the favored direction of this reaction, and the results from the experiment gravitated towards exo-norborneol. Overall, the mechanism demonstrated in this experiment illustrated the ‘accepted’ or simple mechanistic pathway. In actuality, the acid-catalyzed hydration of norbornene has several other complications that are discussed further along this report.

In closer detail, the protonation of water by sulfuric acid when mixed together generated the hydronium ion that was used to protonate the alkene, as well as the bisulfate ion that was used to deprotonate and stabilize water…

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