Chem 3b lab 12 - Experiment 12: The Magtrieve Oxidation Of...

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Experiment 12: The Magtrieve Oxidation Of 4-Chlorobenzyl Alcohol, A Solvent-Free Reaction Purpose : To oxidize 4-chlorobenzyl alcohol(primary) to an aldehyde with out over-oxidation to a carboxylic acid using Magtrieve. Discussion : From the H NMR spectra of the starting material, the hydrogens on the carbons adjacent to the chlorine are on the far left (7.220-7.304) due to the deshielding by chlorine. These peaks are split because of coupling with the other hydrogens on the ring. Those remaining two hydorgens form peaks at 4.557. These peaks are not as deshielded because of the electron density. On the right of the spectrum are peaks at 2.510 signaling the hydrogens on the carbon between the ring and alcohol group. From the 13C NMR of the 4-chlorobenzyl alcohol, the peak at 139.21 is the carbon connected to the chlorine. To the right of that, the peak at 133.29 is the carbons flanking the carbon with the chlorine substituent. At 128.25 and 128.62 are the remaining two chlorines without any substituent. The peaks at 76.81-77.32 signify the remaining carbon on the benzyl ring with the methanol. Finally, the last peak on the right is the carbon adjacent to the alcohol group. In the spectrum for 1H of 4-chlorobenzaldehyde, the peaks at 9.986 signal the hydrogen on the aldehyde group. The peaks on the far right represent the hydrogens on the carbons on both sides of the chlorine. The middle set of peaks at 7.619-7.835 is the hydrogens on the two remaining carbons on the benzene ring. In the 13C NMR of the aldehyde product, the peak at 190.87 marks the carbonyl carbon.
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This note was uploaded on 02/10/2011 for the course CHEM 3b taught by Professor Pederson during the Spring '08 term at University of California, Berkeley.

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Chem 3b lab 12 - Experiment 12: The Magtrieve Oxidation Of...

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