Chem 2211 My Exam 3

Chem 2211 My Exam 3 - Jang, Jaewon 810243 824 am D—om 7::...

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Unformatted text preview: Jang, Jaewon 810243 824 am D—om 7:: M 9/01(/><P?{ N Hlllllllll |IIIHINIH|||||WIHIHIHIVIIMIIHlll CHEMISTRY 2211 EXAM 3 April 7, 2010 SCORE Be sure to read each question carefiilly. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1. 1. (8 pts) Provide the proper IUPAC names for the following compounds in the spaces provided below: 2' # / i 4'“ UJ 0'“ 7' 2. (14 pts) Provide a complete, detailed and stepwise mechanism for the following reaction. In order to receive full credit on must show all electron movement and rovide all of the intermediates for this reaction. Pay careful attention to the stereochemistry of the product. Your intermediates must also be stereospecific: {-‘1’.’ Name __ K) (Ital/L) 3. (8 pts) Provide all of the products, consistent with Markovnikov’s rule, resulting from the addition of one equivalent of HBr to the following compound: In order to receive full credit for this problem, you mpst place eachupf the final products in its appropriately labeled box provided below. You do not need t_0 Show stemochemistry (E/Z or R/S) in your answer‘s). Only skeletal structures are acceptable. Minor Kinetic Minor Thermodynamic {J Name 61"} " ’ _ “ gee/wave 4. (2 pts) Draw the structure of thegangpé‘mfifipfim that forms the following compound after undergoing free radical polymeri'flifio’ri? Free Radical Polymerization (2 pts) Draw the structure of a two monomer segment of the polymer formed from theaeid rcataljged—Qolxmerization of the alkenestarting material provided below; Name ’r 72‘6 V‘JJMn S. (10 pts) Write a series of steps to ac lish the followin s nthetic transformation. You must provide all appropriat ndf ' termedia __ or your synthetic pathway. No reaction mechanisms (aows) arcinecessary to answer this question. [HINTz the stereochemistry of the product is very specific. Be careful.] Cl OCH3 Multiple Step5 ' 1 moie of Acetyiene :::> W + W OCH3 CI 6. (6 pts) Complete the following Diels-Alder reaction schemes by providing either the appropriate diene/dienophile starting materials or all possible reaction product(s). Show specific stereochemistry when appropriate: Br ,1 "L f (6 pts) Provide skeletal structures for all of the possibleuprrgducfls) of the following reaction: Clearlv circle the ma'or roduc KOH ————_—+ CH3CH20H mm “"7 m -r H M‘ HCI _—--—--—> Ether. 25°C KI H3PO4, LOW Temp Name 7 fl. v3 {Mfg UL» Fm, ./ l” 1' , LN . . (ii - 9. (18 pts) Complete the following reaction schemes by adding the appropriate reagent(s), starting material(s), and/or product(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary: 60!; “\“QClg W + O h 0 + M H / Br2 —-—————)- / 1 equivalent 1.) 03 ——-—-——-—-,- 2.) 2n. H3O+ Singl St I '- Reagent oniy tereochemistry mst e e V 1.) 0504 ———————-’- 2.) NaHSOs, H20 10. (18 pts) Complete the following reaction schemes by adding the appropriate starting material(s), reagent(s) and/or product(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary: HCI % ————__+ 2 equivalents Br H3C “Br KOH 2 equivalents 10 ...
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This note was uploaded on 10/05/2011 for the course CHEM 2211 taught by Professor Hubbard during the Spring '07 term at UGA.

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Chem 2211 My Exam 3 - Jang, Jaewon 810243 824 am D—om 7::...

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