11_25_2007_Hunsdiecker Reaction Lab Report

11_25_2007_Hunsdiecker Reaction Lab Report - Hunsdiecker...

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Hunsdiecker Reaction Lab Report (11/26/2007) Norbert Wang (Section 113) From the list of reagents (1, T), it seems that the product could be derived from either lithium  acetate or 4-methoxycinnamic acid. But, from looking at the carbon NMR spectrum one can  see that there are only 7 different carbons in the product. So for the best bet, something  happened to the acid. The acid itself has 8 carbons so NBS must have removed a carbon.  There is no carbon with a chemical shift of around 200 so the COOH group must have been  removed, most likely as CO 2 . The alkene group must have been unaltered because there are  6 carbons with chemical shifts between 100-160ppm indicating that they are either aromatic or  alkene carbons. Most likely, bromine from NBS must have attached onto the end of the alkene  as the COOH was removed to ensure that there are still only 6 different aromatic/alkene  carbons.  The H NMR confirms the observations from the C NMR. There are 2 different kinds of H’s  around 6.5 to 7.5ppm, each having an integral of 2. These match exactly with the 4 hydrogens 
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This lab report was uploaded on 04/05/2008 for the course CHEM 3BL taught by Professor Chunmei during the Spring '08 term at Berkeley.

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11_25_2007_Hunsdiecker Reaction Lab Report - Hunsdiecker...

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