exam2_key - First Three Letters of Last Name: TA Name: Exam...

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Unformatted text preview: First Three Letters of Last Name: TA Name: Exam #2 5.12 Spring 2005 Organic Chemistry | Printed name Signature ID# Pre-requisite (circle one): 5.112 5.111 3.091 1. Make sure your exam has 9 numbered pages plus a periodic table. 2. Write your initials on each page. 3. Look over the entire exam before you begin to familiarize yourself with its length. Do what you know first, then attempt the harder problems. 4. Read the instructions carefully and budget your time. Show all of your work. Partial credit receives points! Page Possible Points Total _\_\ N Tota X 0 (4 pts) Rank the following carbocations in order of stability (1 = most stable). +3° 3° 6 (4 pts) Rank the following alkenes according to energy (1 = lowest energy). Initials Points E] 1 El] 3. (8 pts) For each of the following reactions: label the nucleophile as lone pair (n), pi bond (31:), or sigma bond (0) label the electrophile as empty orbital (a), pi bond (15*), or sigma bond (0*) use curved arrows to show attack of the nucleophile on the electrophile show the product of each reaction DUDE + ,- '. 8) HcEcT + No- ————> O\ ' <¢\ U /\C( m Tl’F lll C ( H \ b) / ——> U + a TF Initials Points [E 2 B 4. (8 pts) Draw a reaction coordinate diagram for a reaction with the following criteria: a) exergonic, 3-step reaction b) the first-step is the rate-determining step c) the second intermediate is more stable than the first intermediate d) the third step of the reaction is faster than the reverse of the second step Energy Reaction Progress Initials Points B 3 [fl 5. (8 pts) Show the product(s) of each reaction. Ignore stereochemistry. O r. V Q , a) / __.1-°a V r J. 0/ +H‘C ” 2. DMS O 2 cm ( O H/\0 CECH b H9504; H2304, H20 \ C —_—> ) I / O 6. (8 pts) Provide products for the following reactions (include all stereoisomers). Indicate if the products are achiral/optically inactive (A) racemic/optically inactive (R), meso/optically inactive (M) or chiral/optically active (C). H Et Ehzfmb n4 Efl, .HH Me; \Et 2. NaBH4 m H Mm Et / l b) me)_>=\ mCPBA t)( O ‘H 5+ H 9“] Me a y’“mZ:&:w + 1 "<:;f‘a ML / a" W/ 2, Mo Initials Points D 4 B 7. (12 pts) Provide the major product of each reaction. Include stereochemistry. a) Br2,H20 —> / >9 \ H 8rd 3 b) H2,Pd/C 0H C) wuuuis 2.H202,Na0H Mags gar l m‘) H / CH3 0H3 “3,? firm Initials w H Points m é“ E 5 8. (6 pts) Provide an appropriate alkyne starting material, reagents and initial product for the reaction in the boxes provided. The number of carbon atoms in the starting material should equal the number of carbon atoms in the final product. no reagents /‘ necessary for this / , \’\ 1. [3% H ; TH l' O\_/ H equilibrium step a ——» mi v—Am g x ileZ, No.0 H H o 9. (6pts) Provide the missing reagents above each reaction arrow and the final product in the box. Et OH OH Et—_—___Me l l \..._ I; 05 w “m” A. N (30 Et 0(- Me 4" 3/:“20 H Me _ of Li) HAL? 1410;) Hio4 or“ lam/mp, mime/idle) melt/H20 10. (8 pts) Provide an alkyne starting material and all necessary reagents to complete the following 2-step reaction. C Hzrz _——> mffiEl Zn C(10) Me 5: Initials Points [3 6 B 11. (18 pts) Provide the mechanism and major product for each of the following reactions. Ignore stereochemistry. (3c. a> WA fl’ V L 1 .. Q 1— 5135 \7' —5 ‘ H 1’ .' BF" HBI‘, ROOR [V Kale—K --> 280' R-o./4—\/?'_f\gfp A KOH + ‘ Er [3p 2 88C mdfl H‘Br "‘5 8p + OflGr Initials Points B 7 E] 12. (10 pts) Propose a mechanism for the following reaction. Ignore stereochemistry. Plagpfi, Initials Points E 8 B EXTRA CREDIT (5 pts) Provide mechanisms for the following reactions. Ignore stereochemistry. l H202, 3 + ,, - H-(HQH + ggsu —% H~O~9; + NaoH ggoH + BCOH)3 Points B ...
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This note was uploaded on 01/30/2011 for the course CHEM 2OA3 taught by Professor Stover during the Spring '10 term at McMaster University.

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exam2_key - First Three Letters of Last Name: TA Name: Exam...

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