organic 2 synthesis paper

organic 2 synthesis paper - Ellyn Velasco Dr Hauser CHE 341...

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Ellyn Velasco Dr. Hauser CHE 341 PM Lab November 30, 2007 A Synthetic Competition Abstract In organic chemistry, there are many ways that a product can be made from a certain starting material. “A Synthetic Competition” tested two out of three different ways that acetophenone could be synthesized into methyl m -nitrobenzoate and determined which way was more cost-efficient. This specific synthesis began with mixing acetophenone (C 8 H 8 O), common bleach (NaOCl), and 10% sodium hydroxide (NaOH) creating benzoic acid. The benzoic acid was then treated with nitric acid (HNO 3 ) and sulfuric acid (H 2 SO 4 ) to nitrate the benzoic acid forming m -nitrobenzoic acid. In the final step of the synthesis, the m -nitrobenzoic acid was refluxed with methanol (CH 3 OH) and sulfuric acid to get the final product of methyl m -nitrobenzoate. With 16.22% yield, though this way only cost $99.97 1 including labor, the melting product, NMR, and IR of the methyl m -nitrobenzoate showed that it was slightly impure.
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Introduction According to the lab handout 2 , there are three ways to synthesize methyl m - nitrobenzoate from acetophenone. Each pathway uses the same reagents and reactions to put together the final product; the difference between them is the order in which the reagents and reactions are used. A Synthetic Competition was designed to find out which of the proposed reaction pathways would be the most cost-efficient. The chosen pathway of this experiment followed this sequence: acetophenone benzoic acid, benzoic acid m -nitrobenzoic acid, and finally m -nitrobenzoic acid methyl m -nitrobenzoate. The first step of this synthesis calls for a nucleophilic acyl substitution in which common bleach (NaOCl) creates a good leaving group from the α -hydrogens converting them all to chlorines 3 . This reaction is then treated with sodium hydroxide (NaOH) in which the nucleophile (-OH) attaches to the carbonyl carbon causing the leaving group created from the bleach to leave. Figure 1 shows the proposed mechanism for this reaction.
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This note was uploaded on 04/27/2008 for the course CHE 341 taught by Professor Hauser during the Fall '07 term at Centre College.

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organic 2 synthesis paper - Ellyn Velasco Dr Hauser CHE 341...

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