Problem_Set_2 - CH 3 COOH 5°C N H NO 2 Write resonance...

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Chem 3580 - Spring 2009 Problem Set #2 1. Propose a synthesis for each of the following compounds from benzene and any other organic and inorganic reagents. Br H O Br OH 2. Heterocyclic aromatic compounds also undergo electrophilic aromatic substitution. Suggest a suitable mechanism for the reaction shown below for furan. Use curve arrows to show the flow of electrons in each step. O Cl O SnCl 4 O O 3. Write a stepwise mechanism for the following reaction. Use curve arrows to show the flow of electrons in each step. Cl + 1. AlCl 3 2. H 3 O + 4. Pyrrole undergoes Electrophilic aromatic substitution preferentially at the 2-position as illustrated below for 2-nitropyrrole. [Note that pyrrole reacts under milder reaction conditions than benzene does. Here, nitric acid in acetic acid instead of nitric acid in sulfuric acid.] N H HNO 3
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Unformatted text preview: CH 3 COOH, 5°C N H NO 2 Write resonance structures for the intermediate formed by attack at 2- and 3-positions of pyrrole. From the examination of the intermediates offer an explanation for the preferential nitration at the 2-position. 4. Treatment of benzene with succinic anhydride in the presence of a strong acid, such as phosphoric acid, gives the following γ-ketoacid. Propose a detailed stepwise mechanism for this reaction. Use curved arrows to indicate the flow of electrons. + O O O H 3 PO 4 OH O O 5. Write down the major product of each of the following reactions. Br O B O n-Bu + Pd(PPh 3 ) 4 NaOH Br (CH 3 CH 2 ) 2 CuLi 6. Write down the major product of the following sequence of reactions. CH 3 1. (CH 3 ) 2 CHCl, AlCl 3 2. HNO 3 , H 2 SO 4 3. KMnO 4 , -OH, heat 4. H +, H 2 O....
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