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Unformatted text preview: Homework 6 CHM 2211 Fall 2009 1. Design three different synthetic pathways starting with the same precursor for the following carboxylic acid : O COOH 2. 2-Chloro-2-methylpentane upon treatment with potassium cyanide gave product of the molecular formula C 6 H 12 . When 2-chloro-2-methylpentane was treated with magnesium turnings in ether followed by dry ice (carbon dioxide) and acidic workup 2,2-dimethylpentanoic acid was obtained. Write both reactions schemes and both products. 3. Complete these acid-base reactions: COOH + NaOH OH COOH + NaHCO 3 COOH OH + H 2 N OH COO- Na + + HCl + NH 3 + H 2 O Li + 4. Show mechanism for the following two step reaction. The first step is an oxidation, followed by the second step which is decarboxylation. Do not forget to show mechanism for tautomerization of the enol into respective ketone. COO H O C H COO H O O isocitrate + isocitrate dehydrogenase Mg 2+ NADH -ketoglutarate NAD + + + co 2 5. Each of these acids undergoes thermal decarboxylation. Draw the structural formulas for enol intermediates 5....
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