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Bromine addition - Andre Hinojosa 12601675 Patners Chelsea...

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Andre Hinojosa 12601675 Patners: Chelsea Azevedo, Tara Chamberlain 8/12/10 Stereochemistry of Bromine Addition to Trans-Cinnamic Acid In this experiment we analyzed the addition of bromine to trans-cinnamic acid through melting point identification to find out by which mechanism the bromine attaches to the acid. Through the different physical properties of the trans vs. cis-cinnamic acid, the melting point for trans being 202-204˚C and only 93-95˚C for the syn isomer. There are many ways for the bromine to attach to the compound but each way would produce various products. To obtain syn addition, the double bond from the carbons would break and attach to one of the bromides in the bromine. Simultaneously, the other bromide would attack the other carbon, syn-addition would result creating a compound with both bromides on the same side. If this same process occurred but a carbocation formed on the respective carbon, we would get a racemic mixture of both trans and cis- isomers, also depressing the melting point than each pure respective compound. This is due to the trigonal planar structure of the
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