Prelim_3_modified_solution

Prelim_3_modified_solution - Organic Chemistry for the Life...

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1 Organic Chemistry for the Life Sciences Chemistry 358 Spring Semester 2007 Prelim 3 April 12, 2007 7:30-9:00 PM Name: (Last) (First) (Middle Initial) Do not open until the proctor tells you to do so. There are 10 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. (10) 2. (12) 3. (15) 4. (12) 5. (15) 6. (18) 7. (18) Total (100)
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2 1. (a)(2 Points) Select the most and the least reactive compound in the first step (formation of the tetrahedral intermediate) of a nucleophilic acyl substitution reaction. A . Phenyl acetate B . Cyclohexyl acetate C . p -Methylphenyl acetate D . p -Chlorophenyl acetate. Most reactive D Least reactive B (b) (2 Points) From the same list in 1(a) select the most and the least reactive in the second step (collapse of the tetrahedral intermediate) of a nucleophilic acyl substitution reaction. Most reactive D Least reactive B (c) (4 Points) Draw the reaction energy diagram for a nucleophilic acyl substitution reaction in which (i) the first step is rate-limiting and (ii) the second step is rate-limiting. Assume that in (i) the product is
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This note was uploaded on 04/22/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell.

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Prelim_3_modified_solution - Organic Chemistry for the Life...

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