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E1,241b,S05 - EXAM 1 CHEMISTRY 241b Dr Spurgeon ANSWER KEY...

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EXAM 1 CHEMISTRY 241b February 10, 2005 Dr. Spurgeon ANSWER KEY __________________________________________________________________________________________ 1. (8 points) Circle the molecules that are aromatic (assume planarity). 2. (12 points) Provide acceptable names for the following compounds: a. b. c. d. N H S N H N O O OH CH 2 CH 3 H 3 CH 2 C CN NO 2 CH 3 O Br Br Anthracene 2,6-Diethylphenol 3-Nitrobenzonitrile 3,4-Dibromoacetophenone
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3. (6 points) For each molecule below circle the MOST likely position for an electrophilic aromatic substitution reaction. 4. (28 points) Complete the following reaction schemes by providing the required starting material(s), reagent(s), and/or MAJOR product(s). CH 3 NO 2 O Br CH 3 OCH 3 NaNH 2 SO 3 H 2 SO 4 + CH 3 In what year were the discoverers of this reaction awarded the Nobel Prize in Chemistry (circle): 1935 1950 1962 1989 1. NaOH 2. Work-up 1. CH 3 CH 2 CH 2 Cl, AlCl 3 2. H 2 O, cat. acid CH 3 CH 2 COCl AlCl 3 Name of this reaction:_______________________________ Br 2 , FeBr 3 Br 2 FeBr 3 Br Br SO 3 H Br OH Br OH Br Br Br O Friedel-Craft Acylation
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5. (20 points) Provide a complete synthesis for the molecules shown below. You must start with the starting
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