Q2_Wi04 - NU, Winter 2004, Quiz 2 2 1. (8 pts) Complete...

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NU, Winter 2004, Quiz 2 2 1. (8 pts) Complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. For EAS reaction, assume that you can separate the ortho- and para- products. i. Br O 2 N ii. iii. (8 pts) The Friedel-Crafts reaction of pyrrole with acetyl chloride and aluminum chloride yields 2-acetyl pyrrole. Draw a mechanism to explain this selectivity showing all the appropriate resonance structures which influence the reaction. Provide all proton transfer steps. N H Cl O + excess AlCl 3 N H O
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NU, Winter 2004, Quiz 2 3 2. a. (4 pts) Using Huckel’s rule only, classify the following molecules as likely to be planar or non planar. Write your answers below the molecule. If you cannot tell, say so. + H 2- H H b. (4 pts) Using Hückel’s rule only, classify the following planar molecules as being aromatic, antiaromatic, or neither. Write your answers below the molecule. If you cannot tell, say so.
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Q2_Wi04 - NU, Winter 2004, Quiz 2 2 1. (8 pts) Complete...

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