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CH118K Norbornene

CH118K Norbornene - The broad peak is OH and the sharp...

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Michael Tam(mht347) 3/25/2011 Hydration of Norbornene In this experiment, acid catalyzes water across a C=C bond. This is also known as Hydration of an alkene. “Mechanistically, this is process is simply the reverse of the acid-catalyzed dehydration of alcohols.” (Gilbert, J. Experimental Organic Chemistry ) The equilibrium position for this pair of reactions depends on the reaction conditions. To drive the reaction towards hydration, we use an excess of water, keeping in mind that the acid is a catalyst. One of the most important things we have to do is choose the correct acid. Hydrochloric acid is a bad choice because the anion formed, Cl - , can compete with the OH - in reacting with the alkene. We use H 2 SO 4 because it is not only a strong acid, but its anion won’t react with the alkene. The attached spectra is an IR of our product, Norborneol. It matches the book’s IR on page 388.
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Unformatted text preview: The broad peak is OH, and the sharp peaks immediately after are the hydrocarbons (The peaks are labeled on the spectra). The spectra obtained support the theory. MP amount put in amount recovered % Recovery 119 o 1 g .562g 47.2% Note: Norborneols MW is 112 whereas Norbornenes is 94. Therefore, if we got 100% yield, we would expect 1.19 grams. The MP is consistent with the MP of our expected product, Norborneol, and the % recovery is within the range of what Dr Fjetland said was normal. The data obtained supports the theory. Potential sources of error include improper scraping of the crystals after sublimation, neglecting to cool the acid-norbornene mixture, and separating the organic layer from the aqueous....
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