Chem 14D Final Exam. Spring 2010 / Prof. Neil Garg. Thursday, June 10, :30 AM 2:30 PM
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1 General Instructions: Chem 14D Final Exam Spring 2010 / Prof. eil Garg This is a standard closed-note exam. Thursday, June 10, :30 AM 2:30 PM Chem 14D Final Exam P.1 Please read each question carefully and write your answer neatly in the space provided using a black or blue pen (no pencils!). Scrap paper and a periodic table are provided on the final pages of the exam. You may detach these pages from the rest of the exam. The use of model sets is allowed. Cell phones, calculators, headphones are not permitted. Keep your Student ID card out for ID Check. GD LUCK! Problem Possible Points Score Bonus 10 Total bonus PLEASE PRIT & SIG YUR AME BELW T ACKWLEDGE TAT YU WILL ADERE T TE CEM 14D R CDE: n my honor, I will not give or receive any unauthorized aid on this exam. Print ame / Student ID# Sign ame
2 Chem 14D Final Exam P.2 1. Draw the major product for each of the following reactions. Where applicable, answers without relative stereochemistry will be given zero credit. (2 points each, 20 points total) a. Et 2, Pd/C Et b. + heat c. n-butyllithium d. + (excess) e. + Et Et
3 1. Continued from previous page Chem 14D Final Exam P.3 f. 3 2 S 4 2 g. Mg (2 equiv) h. LiAl 4 i. 2 2 F 3 CC 3 j. 2 fuming 2 sulfuric acid 3 S
4 Chem 14D Final Exam P.4 2. Provide the missing reagents for the transformations shown below. (2 points each, 20 points total) a. PCC b. 1. B , a c. 2 Ac d. 2 Fe 3 e. Zn(g), Cl, heat or 2 2, K, heat or Pd, 2, Et
5 2. Continued from previous page Chem 14D Final Exam P.5 f. 1. LDA 2. I g. PCl 3 or SCl 2 Cl h. 2 heat i. Cr 3 +, 2 j. a, 2 eat
6 Chem 14D Final Exam P.6 3. Provide a potential precursor to each of the following compounds (in other words, perform a singlestep retrosynthesis). Also draw out the corresponding forward reaction with reagent that could be used to synthesize the given molecule. (4 points each, 20 points total) ote: In many cases, there is more than one correct solution a. Identify precursor(s): Forward reaction (provide starting material and reaction conditions): cat. 2 S 4 benzene, heat b. Identify precursor(s): Forward reaction (provide starting material and reaction conditions): MCPBA
7 3. Continued from previous page c. Identify precursor(s): Chem 14D Final Exam P Forward reaction (provide starting material and reaction conditions): 2 2 Fe 3 2 d. Identify precursor(s): Forward reaction (provide starting material and reaction conditions): + 2 e. Identify precursor(s): + Forward reaction (provide starting material and reaction conditions): + a, 2 heat
8 Chem 14D Final Exam P.8 4. Provide detailed arrow-pushing mechanisms for the following transformations. (5 points each, 10 points total) a. Et +, eat Et + Et Et Et Et + Et Et Et Et b. Ac
9 Chem 14D Final Exam P.9 5. Provide syntheses of the following target molecules. You may use common reagents, fragments of 2- carbons or less (these fragments may contain atoms other than just carbon, including hydrogen, oxygen, Mg, and Li), and any of the compounds shown in the Chem 14D Toolbox. It is not necessary to show mechanisms or a retrosynthetic analysis in your solution. (10 points each, 30 points totals) Chem 14D Toolbox Cl a. b. c. (naproxen, also known as "Aleve") Place your final answers for questions 5A, 5B, and 5C on the subsequent pages
10 5a. Chem 14D Final Exam P.10 (naproxen, also known as "Aleve") 1. Mg P 3 1. Mg C 2 [several possible solutions]
11 5b. Chem 14D Final Exam P.11 C 2 C 2 1. n-butyllithium + heat 2 2. C 2 Pd/C [several possible solutions]
12 5c. Chem 14D Final Exam P Zn(g) 2 Cl 2 2 S 4 Cl Fe 3 [several possible solutions]
13 Bonus #1: Fill in the blank (1 points): Chem 14D Final Exam P.13 Fischer received the oble Prize in Chemistry in the year Bonus #2: Draw the product of the following reaction (you must show a structure). (2 points extra credit) see lecture notes 3/29/10, Exam 1, Exam 2, TA music video 2 a acetone IDIG! Bonus #3: Consider the structure of sarain A. This beastly molecule is typically drawn with a dotted line between 1 and C2, as shown below. Explain what this dotted line represents. (3 points) 2 1 sarain A proximity interaction = the lone pair on 1 can attack the C2 carbonyl. Bonus #4: Provide a plausible synthetic scheme for the conversion of compound A to compound B (4 points)? A B A heat B Intramolecular Diels-Alder!
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