Chem 3BL - Lab Report E#17 - Kylie 01 November 2010 Chem 3B...

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Kylie 01 November 2010 Chem 3B Lab Experiment #17: A Dehydrogenation/Hydrogenation Reaction Discussion: NMR Spectra To determine the structure of my product, I first drew out the possible mechanism of the dehydrogenation/hydrogenation reaction, which would result in a benzene ring and the conversion of the carbonyl oxygen into an -OH group (also, the isopropenyl's C=C bond would be hydrogenated, resulting in an isopropyl). The NMR spectra proved that it was a phenol compound, with the OH group's hydrogen represented by the unique singlet (at around 6 ppm), and the 3 hydrogens on the aromatic ring represented by the shifts at high ppm values that are associated with benzene 1H shifts (6-8.5 ppm). The methyl and isopropyl substituents also corresponded with the NMR results, represented by lower ppm values and the absence of alkene shifts. Also, HE and HF were represented by a doublet due to the neighboring HG in the isopropyl substituent (and HG's shift shows splitting by these 6 H's). Energetics C-H formed (-413 kJ/mol), C-C broken (+347 kJ/mol) C-H broken (+413 kJ/mol), C-C formed (-347 kJ/mol) Total: 0 kJ/mol C-H broken (+413 kJ/mol), C-C formed (-614 kJ/mol), O-C broken (+375kJ/mol), O-H formed (-464 kJ/mol) Total: -290 kJ/mol
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C-H formed (-413 kJ/mol), C-C broken (+347 kJ/mol) C-H broken (+413 kJ/mol), C-C formed (-347 kJ/mol) Total: 0 kJ/mol
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This note was uploaded on 06/27/2011 for the course CHEM 3BL taught by Professor Chunmei during the Fall '08 term at University of California, Berkeley.

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Chem 3BL - Lab Report E#17 - Kylie 01 November 2010 Chem 3B...

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