CH118K Stilbene - 240 65.08% Note: Our product gained wait...

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Michael Tam Period 10 Bromination of (E)-Stilbene In this lab we determine the stereochemistry of the electrophillic addition of bromine to E stilbene. The bromination of E stilbene to give meso stilbene dibromide is an electrophilic addition reaction. In this reaction, two products can be formed. Meso stilbene is formed from the nucleophilic attack of the bromine onto the cylic bromide ion. Dl stilbene dibromide is also formed, but in lesser quantity Why is the main product meso stillbene? In the reaction, both forms are possible, but the main form is more probable because the interconversion of 50 on page 376 from the text with and the acyclic carbocation doesn’t happen very often. Original Final(Recrystalized) MP %Yield .909 g 1.1g
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Unformatted text preview: 240 65.08% Note: Our product gained wait because the molecular weight of our product is higher than the stilbene without bromine. The theoretical, 100% yield is 1.69g. this was found by taking the original .909 and dividing it by the molecular formula of the stilbene to get moles, and then multiplying it by the molecular weight of the product. All in all, the experiment was successful in backing up the theory because the product had a melting point of 240, which is the correct melting point of the diastereomer we wanted. The other melting point we could have obtained would be 100 degrees lower, had the other diastereomer been formed. Additionally, the % yield was in very good standing in what was expected....
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This note was uploaded on 09/25/2011 for the course CH 118K taught by Professor Fjetland during the Spring '08 term at University of Texas at Austin.

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