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Problem Set 2 - electrons in each step Cl 1 AlCl 3 2 H 3 O...

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Chem 3580 - Spring 2010 Problem Set #2 Text Problems Chapter 15: 36; 38b, c, g; 39; 42b, d, f, h; 44a, d, f; 47; 48a, c, e, g; 49b, d, e, f; 52, 54; 55; 61a, c; 66, 68, 69 ———————————————————————————————————————————— Additional problems 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
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Unformatted text preview: 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 is sufficient.] N H HNO 3 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. 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...
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