Prelim_2_S09_Answers - Name: (Last) (First) (Middle...

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Name: (Last) (First) (Middle Initial) 1 Circle Lecture time – 9:05 or 10:10 Organic Chemistry for the Life Sciences Chemistry 3580 Spring Semester 2009 Prelim 2 - Answers March 10, 2009 7:30-9:00 PM Read each question very carefully. There are 9 total pages. Please, count your pages before beginning the exam. Write all answers on the printed side of the exam. Draw structures clearly. It is your responsibility to convey information unambiguously and not the grader’s responsibility to interpret what you meant. 1. (8) 2. (10) 3. (18) 4. (12) 5. (10) 6. (14) 7. (14) 8. ( 14) Total (100)
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Name: (Last) (First) (Middle Initial) 2 1. (8 Points) (a) From the list below select the compound you would expect to react fastest and one that would react slowest in base-catalyzed ester hydrolysis. A . p -Nitrophenyl acetate B . Phenyl acetate C . p -Methoxyphenyl acetate D . p -Methylphenyl acetate. Most reactive A Least reactive C (b) From the list below select the most and the least reactive compound in nucleophilic addition reaction to its carbonyl carbon. Br O O H O Br H O A B C D Most reactive D Least reactive B (c) Select the compound that has the most and the one that has the least acidic α -H. H O OCH 3 O O O A B C D Most acidic α -H A Least acidic α -H D (d) Select the strongest and the weakest carboxylic acid from the list below . Phenylacetic acid Diphenylacetic acid 3-Phenylpropanoic acid Strongest Diphenylacetic acid Weakest 3-Phenylpropanoic acid
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Name: (Last) (First) (Middle Initial) 3 2. (10 Points) (a) Provide reasons for each observation below. Provide the chemical equations for each reaction and use structures to clarify your answers. Do not write detailed mechanisms.
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This note was uploaded on 05/13/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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Prelim_2_S09_Answers - Name: (Last) (First) (Middle...

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