wittig reaction
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wittig reaction

Course Number: CHEM 368537, Spring 2009

College/University: Berkeley

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Carlos Caceres Chemistry 3B lab The Wittig Reaction Purpose: To use the Wittig reaction to produce an oxide and an alkene. Data: 173 mg Methyl Acetate added 76 mg Nitrobenzaldehyde Added- Yellow crystals 100mg silica gel added- white powder After the microwave, product had turned into a caramel color, powdery mixture. Theoretical Yield: 173 Mg Percent Yield: 57.97% Melting Point: 49.3-52.4C Discussion: The 2...

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Caceres Carlos Chemistry 3B lab The Wittig Reaction Purpose: To use the Wittig reaction to produce an oxide and an alkene. Data: 173 mg Methyl Acetate added 76 mg Nitrobenzaldehyde Added- Yellow crystals 100mg silica gel added- white powder After the microwave, product had turned into a caramel color, powdery mixture. Theoretical Yield: 173 Mg Percent Yield: 57.97% Melting Point: 49.3-52.4C Discussion: The 2 alkene isomers formed in the reaction are E and Z isomers. By looking at the NMR spectra of the product, you can see that there are smaller peaks with smaller integration values. This shows that although both isomers were produced, one was made in greater quantities. By simply looking at the 2 structures of the products, I can assume that the E alkene was produced because it has less steric hindrance than the Z alkene. By performing the reaction in silica gel, you can ensure a better mixing between the product and the silica gel, resulting in better separation between the formed products. This results in better separation between the mixed products. From the TLC plates, you can tell that fractions 2 and 3 contained only one product. The rest of the vials contained 2 products. By looking at the structures of the products, it can be seen that the alkene is much larger than the triphenylphosphine oxide. Since the silica gel is incredibly porous, the smalled oxide will spend more time trapped in the stationary phase. The alkene will favor the moving phase because of its size and will be the first product to come out of the column. If I had wanted to further separate the mixtures, I could have use a longer column. That would have isolated more of the alkene. Making more runs through the column would also isolate more of the alkene. Arrow pushing mechanism: Conclusion: This experiment used the wittig reaction to form an alkene and a triphenylphosphine oxide. The two products were then separated using column chromatography, a new chemistry technique. This also showed NMR that can be split by phosphorus and how the presence of cis and trans makes life a lot harder with more peaks. Questions: 1. this particular stabilized ylide can be stored in a bottle because it is incredibly stable. The particularly high stability of this compound may be due to the interaction between the electron rich oxygen on the nitrogen substituent and the nearby phosphorus of the ylide. The example given does not have the nitrogen group, making it relatively unstable. 2. The procedure is important because it ensures that all of the desired products are absorbed into the silica gel instead of being dissolved in the solution right above the gel. This is important because only the product is separated in the silica gel. If the products were to be dissolved above the gel, the products in the silica gel and the products above it would be different, which would result in a mixed product when a fraction is measured. This mixed fraction would then have less product. Through this process, it insures than none of the products are dissolved in the solution above the column, meaning a better separation between the two products, which would ultimately mean a larger percent yield gathered at the end of the experiment. 3. through the TLC plate, the researcher can tell that products 6-10 belong to his purified product because only one dot shows up. If he wants to maximize his percent yield, he can run vials 3-5 again several times because they all contain a mixture of the product he wants. He can then combine those vials with the initial pure vials. He can repeat this procedure as many times as he wants. 4. this reaction would be particularly useful if you wanted to do a wittig reaction without breaking the C0 double bond. This reaction breaks a CC bond and creates a CC double bond without disturbing the CO double bond. This reaction also adds an O to the carbon, which can be attached to any C group, making the reaction particularly useful for long chains. 5.

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Chapter 6Insurance Company OperationsCopyright 2008 Pearson Addison-Wesley. All rights reserved.Credit [Insurance] Score The Fair Credit Reporting Act (FCRA) requires notice to a consumer subjected to "adverse action . based in whole or in part on any
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Chapter 7Financial Operations of InsurersCopyright 2008 Pearson Addison-Wesley. All rights reserved.Agenda Property and Casualty Insurers Financial Statements Measuring Financial Performance Life Insurance Companies Financial Statements Measuring F
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Chapter 9Fundamental Legal PrinciplesCopyright 2008 Pearson Addison-Wesley. All rights reserved.AgendaPrinciple of Indemnity Principle of Insurable Interest Principle of Subrogation Principle of Utmost Good Faith Requirements of an Insurance Contract
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Chapter 26Commercial Liability InsuranceCopyright 2008 Pearson Addison-Wesley. All rights reserved.Agenda General Liability Loss Exposures Commercial General Liability Policy Employment-related Practices Liability Insurance Workers compensation insura
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