Lab 1: Dehydrogenation/Hydrogenation

Lab 1: Dehydrogenation/Hydrogenation - Lab 1 A...

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Lab 1: A Dehydrogenation/Hydrogenation Reaction Discussion: The aromatic product is a phenol derivative formed from reacting the R -carvone with Pd/ C. According to the 1 H NMR of the product of the reaction, there are 6 equivalent hydrogen atoms as opposed to 3 in carvone; this suggests that the double bond of the bottom isopropenyl group must have been broken. Next, the 13 C[ 1 H] NMR of the product shows that the highest ppm of carbon is 153.19 instead of 198.49, which means that the carbonyl was turned into an alcohol. Since these two double bonds were broken, more hydrogen bonds were formed. However, the 1 H NMR of carvone and that of the product indicate that both compounds contain 14 hydrogen atoms. Therefore, to preserve the amount of hydrogen bonds, the cyclohexene gives up two equivalents of hydrogen to yield benzene; the product is a phenol with methyl and isopropyl substituents. Since the molecular weight of the product is 150 g/mol and 0.0009 moles of R-carvone were reacted, the theoretical yield is (150 g/mol) × (0.0009 mol), which is equal to 0.135 grams. The actual yield was 0.055 grams; thus, the percent yield of the product is (0.055 g) ÷ (0.135 g) × (100%) = 40.7%. Starting with the enol form of carvone, an approximate
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This note was uploaded on 10/03/2011 for the course CHEM 3BL taught by Professor Chunmei during the Spring '08 term at Berkeley.

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Lab 1: Dehydrogenation/Hydrogenation - Lab 1 A...

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