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Sample Midterm 2 - 5 What is the structure of the compound...

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Sample midterm CHM 2120A 2010 1. Provide a synthesis of the following compound starting from bromobenzene. (12 pts) Br O N O 2 S OH
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2. Provide a detailed mechanism for the following reaction. Include resonance structures to justify your regiochemistry. S O SO 3 H 2 SO 4
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3. Provide syntheses of the following aromatic compound from the starting material indicated and benzene. NO 2 Cl OH
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4. What is the structure of the compound with molecular formula C 12 H 18 O and the IR and NMR spectra shown below?
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Unformatted text preview: 5. What is the structure of the compound with molecular formula C 5 H 8 O and the IR and NMR spectra shown below? 6. Give the major organic product of each of the following reactions. Mechanisms are not required, but part marks might be given for incorrect answers with plausible mechanisms. (8 points) a. OsO 4 , NMO b. (elimination) Ph Cl HOCH 3 (solvent) NaOCH 3 c. O 1. KCN 2. H 3 O + d. OH 1. ClSO 2 CH 3 , weak base 2. NaNHCH 3...
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