chem3a-fall02-final-Pedersen-exam

chem3a-fall02-final-Pedersen-exam - Dr. Steven Pedersen...

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1 Dr. Steven Pedersen December 11, 2002 Chemistry 3A Final Exam Student name: _________________________________________ Student’s signature: ______________________________________ TA’s name or section number:_______________________________ M Problem 1 ________ (31 pts) I Problem 2 ________ (51 pts) D Problem 3 ________ (18pts) T Problem 4 ________ (52 pts) E Problem 5 ________ (48 pts) R M Problem 6 ________ (74 pts) Problem 7 ________ (73 pts) Problem 8 ________ (73 pts) Total Points _________ (420 pts) No Calculators Allowed Be Sure Your Exam has 17 Pages Be Sure To Try All Parts of a Problem! 1.
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A. Provide one, and only one, real example for each of the following terms or draw a structure for a given chemical name. (31 pts) MCPBA an epoxide diisopropyl ether Z-2,3-dimethyl-2-penten-1-ol cis-3-heptene 1B. Calculate the degree of unsaturation for the molecular formula shown below. You must show your work to receive any credit. Draw TWO REAL molecules that are consistent with your calculation. C 4 H 6 ClN Don' forget to draw two real molecules that fit this formula. 2. Predict the product(s) from the following reactions. (51 pts) 2
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HO Br Br H OH O OMe H 2 SO 4 H 2 O NaBH 4 MeOH C 5 H 12 O C 5 H O (different from starting material) all possible stereoisomers (be sure to show wedges and dashes) + NaH an optically ACTIVE product (be sure to show appropriate stereochemistry) an optically INACTIVE ACYCLIC product + NaH Continued on next page 3
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DD OH OSO 2 CF 3 H H D D H 2 SO 4 1. BH 3 2. H 2 O 2 , H 2 O, HO + Br 2 + HBr + MeO heat H 2 O 4 alkenes two major stereoisomers (be sure to show wedges and dashes) reaction proceeds through a carbocation intermediate the product is an alkene Continued on next page 4
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O OH HO Br the major product + Mg an optically active product (be sure to show appropriate stereochemistry) + H 2 Pd/C + LDA PCC no H 2 O 3. Match the molecules shown below with the statements. (18 pts) 5
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a.
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This note was uploaded on 02/08/2010 for the course CHEM 1A taught by Professor Nitsche during the Spring '08 term at University of California, Berkeley.

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chem3a-fall02-final-Pedersen-exam - Dr. Steven Pedersen...

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