(11-25-07) hunnsdiecker

(11-25-07) hunnsdiecker - likely that the product was...

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Arthur Yu Genevieve van de Bittner, Chem 3BL 113 The Hunsdiecker Reaction Discussion 1) Analysis of spectral data began with the starting material p-methoxycinnamic acid in mind. It was easy to see the similarities, especially the presence of the alkene and aromatic carbons and hydrogens. An examination of the C spectra yields a total of 7 different C, as opposed to 8 in the starting compound. Additionally, one would expect a very noticeable peak at 200 due to C-OOH – it is not there! Mass spec’s molecular ion (the highest actual peak [not the tiny 1% isotope-caused highest peak]) is around 215 m/z. This corresponds to 178 (-cinnamic acid) – 45 (loss of COOH) + Br81 (50% abundance. From NBS) = 214. With Br79 (50% abundance) it becomes 212, which matches the base peak. Combined with the NMR data, it is
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Unformatted text preview: likely that the product was p-methoxycinnamic acid with the COOH group replaced by Br. 2) please see attachment 3) There should have been CO 2 evolution, but none was observed. It is likely that the high stirring speed (8+) may have made hidden any CO 2 . 4) please see attachment 5) Succinimide is highly polar and should have favorable interactions with the acetonitrile and water solvents. The product, on the other hand, is not as compatible. It is likely that the Hirsch funnel step eliminated nearly all of the succinimide. Conclusion The Hunsdiecker reaction further adds to the versatility of carbonyl derivative compounds. In the conversion from carboxylic acid to the reactive bromine along with the breaking of a carbon bond, more synthetic routes are opened up....
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This note was uploaded on 04/04/2008 for the course CHEM 3BL taught by Professor Chunmei during the Fall '08 term at Berkeley.

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