Exam II Key - Chem. 310N, Spring 2008 Professor Krische...

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Chem. 310N, Spring 2008 Professor Krische Midterm Exam II Average = 50 Grading Scale 90-100 = A+ 80-89 = A 70-79 = A- 65-69 = B+ 60-64 = B 55-59 = B- 50-54 = C+ 45-49 = C 40-44 = C- 37-39 = D+ 33-36 = D 30-32 = D- 0-29 = F
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N a m e : Problem 1. (16 points) 2. (24 points) 3. (12 points) 4. (18 points) 5. (20 points) 6. (10 points) Total Points: /100
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1. (16 points) For the following pairs of compounds, circle the compound that reacts faster with the indicated nucleophile. For the faster reacting compound only , draw the product of its reaction with the indicated nucleophile. A. v e r s u s O OCH 3 Cl 3 C O Then Dilute HCl (aq.) CH 3 MgBr (2 Equivalents) H 3 CO C H 3 3 3 C HO 3 B. Cl O O CH 3 Cl CH 3 O v e r s u s CH 3 H N H 3 C Pyridine NC 3 H O H 3 C CH 3 C. v e r s u s O O O O NaBH 4 (2 Equivalents) Then Dilute HCl (aq.) HO OH D. v e r s u s HS O O O O O HO O S O
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2. (24 points) Hydrolysis of benzonitrile produces benzoic acid. The hydrolysis occurs in two stages. The first stage involves hydrolysis of the nitrile to furnish an amide. The second stage involves hydrolysis of the amide to furnish an acid. Propose a mechanism to account for the benzonitrile hydrolysis. For each intermediate, draw all lone pair electrons, any formal charges, and
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This note was uploaded on 04/09/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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Exam II Key - Chem. 310N, Spring 2008 Professor Krische...

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