1. What would you expect the IR to show? 2. Can IR be used to distinguish starti
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1. What would you expect the IR to show? 2. Can IR be used to distinguish starting material and product? Why? 3. What are some other possible products? 4. How would you distinguish the metaproduct from the others? (discuss 1HNMR, MS, IR, and MP) 5.Which would be the major product? Why? Please answer all of the questions completely! Profesor Kasbleon V. Kilway,Department of Chemistry, University of Missouri-Kansas City,2007-CHEM 322 7. Nitration of Methyl Benzoate M. Jones: Electrophilic Aromatic Substitution, Nitration, 14.4e, pp 686-687 Disubstituted Benzenes: ortho, meta, and para Substitution, 14.9, pp 704-717. This procedure has been adapted from the microscale procedure described in the third edition of Macroscale and Microscale Organic Experiments by Kenneth L. Williamson (Houghton Mifflin, Boston, 1999). Background In this laboratory, you will be nitrating methyl benzoate with nitric acid using sulfuric acid as your catalyst. Methyl benzoate is a methyl ester. As in our previous naming conventions, the "e" suffix of the alkane is replaced by "-oate Therefore, benzene becomes benzoate. Then, the other part of the ester (may be considered the ether portion) is put in front of the benzoate. Since the product is a methyl ester, the methyl comes before the benzoate. CO2CH3 O2CH3 HNO3 H SO NO2 Methyl benzoate bp 198-199 ° M.W. 136.15 d 1.09 Methyl 3-nitrobenzoate mp 78 °C M.W. 181.15 Figure 1. The overall reaction for the nitration of methyl benzoate. The overall reaction is depicted in Figure 1. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, and its general mechanism is summarized in Figure 2. 322L Experiment 7: Nitration of Methyl Benzoate1Explanation / Answer
1. Ir spectrum gives extra 2 peaks in the product than reactant for this nitration of methyl benzoate.
2. Yes, it helps alllot in differentiatin the reactant and product. Since product has NO2 group in its structure and it gives two peaks at 1340 and 1560 for symmetric and asymmetric stretching respectively.
3. Alogn with meta nitro substituted produt , ortho and para substituted prodcuts are also formed in minor quantities.
4. IR differentiates by presence of NO2 group in the product, Mass differentiates by m/z vlaue of NO2 group (Odd mass due to odd no of nitrogen-Nitrogen rule);H-NMR : before reaction a multiplet for 5 protons and after reaction seperate signals for 4 aromatic protons and the protons ortho to NO2 group appears at more down field than earlier nand C-NMR gives signal for NO2 carrying carbon appears at more down field.
5. Meta isomer is the major , since the ester is deactivating group and orients the new incoming group towards meta position.
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