Chem_358_Prelim_2_S07_answers - Organic Chemistry for the...

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Organic Chemistry for the Life Sciences Chemistry 358 Spring Semester 2007 Prelim 2 - Answers March 13, 2007 7:30-9:00 PM Name: (Last) (First) (Middle Initial) Do not open until the proctor tells you to do so. There are 8 total pages. Please, count your pages before beginning the exam. Write all answers on the printed side of the exam in the locations indicated. Draw structures clearly. It is your responsibility to convey information unambiguously and not the grader’s responsibility to interpret what you meant. 1. (24) 2. (14) 3. (10) 4. (12) 5. (16) 6. (14) 7. (10) Total (100)
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2 1. (a) (2 Points) Circle the carbonyl compound that will form the most stable hydrate. O O Cl O O 2 N O CH 3 O (b) (2 Points) Circle the compound you would expect to be the most reactive in nucleophilic aromatic substitution reactions. CF 3 NO 2 CF 3 NO 2 CF 3 Br Br Br NO 2 (c) (6 Points) Circle all the isoprene units in only those structures that can be classified as terpenes . O O H H or (d) (6 Points) What mass/charge ( m/z ) ratio would be expected in a mass spectrum of the compound shown below as a result of McLafferty Rearrangement. Show the details of how you arrive at your answer. m/z = 72 O O H . .. O H . m/z = 72 (e) (4 Points) What are the key differences you would expect to see in the 1 H NMR spectra of the two compounds shown below? O
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This note was uploaded on 04/03/2008 for the course CHEM 3580 taught by Professor Sogah, d during the Spring '08 term at Cornell University (Engineering School).

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Chem_358_Prelim_2_S07_answers - Organic Chemistry for the...

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