Practice_Final_Chem_3045-Answers3

Practice_Final_Chem_3045-Answers3 - Cl O 1 2 PhMgBr...

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Practice Final Chem 3045: 1) Write the mechanism for the bromination of cyclohexane. 2) Propose a mechanism for the following: O H 2 SO 4 3) Write the product(s) of the following reactions paying attention to regio- and stereochemistry where applicable. O O O O O O O O O 1 eq. O O H H O O O O O 1) O 3 , CH 2 Cl 2 , -78 o C 2) Zn, CH 3 COOH O O O O O O 1) Hg(OAc) 2 , MeOH 2) NaBH 4 O HBr Br
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1) BH 3 2) HOOH/OH - /H 2 O OH HBr, ROOR Br NBS, light Br major minor Br Br Br 2 Br Br Br 2 OH O Br O O OH Cl 1) 2) H + , MeOH OH O O O OH Cl 1) 2) MeO - O OH Li, NH 3 , ROH H 2 , lindlar 1) NaNH 2 2) CH 3 CH 2 Br 1) NaNH 2 2) CH 3 CH 2 Br NR 1) R 2 BH 2) HOOH/OH - /H 2 O O
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HgSO 4 , H 2 SO 4 O H 3 C I CH 3 S H 3 C S H 3 C Br CH 3 O H 3 C Br CH 3 O Br CH 3 OH O Cl AlCl 3 AlCl 3 Cl O O AlCl 3 Cl O 1) 2) H 2 NNH 2 , OH - 1) H 2 SO 4 , HNO 3 , heat 2) H 2 , Pd 3) NaNO 2 4) CuCl Cl 1) H 2 SO 4 , heat 2) D 3 PO 4 D 1) FeBr 3 , Br 2 2) Mg, Et 2 O 3) D 2 O D
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AlCl 3
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Unformatted text preview: Cl O 1) 2) PhMgBr Ph=phenyl 3) H 3 O + OH AlCl 3 Cl O 1) 2) H 2 NNH 2 , OH-3) NBS, light 4) (CH 3 CH 2 )CuLi AlCl 3 Cl O 1) 2) CH 3 MgBr 3) H 3 O + 4) NaH, CH 3 CH 2 Br O 4) How would you synthesize the following starting from materials with five carbons or less, benzene, and any other reagents? (Assume ortho and para can be separated.) Cl OH HO OH Br OH O S 5) Show how you would synthesize the products from the given starting materials plus benzene, reactants with 5 carbons or less and any other reagents: O OH O O H 2 N...
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This note was uploaded on 02/26/2012 for the course CHEM 3045 taught by Professor Breslow during the Fall '09 term at Columbia.

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Practice_Final_Chem_3045-Answers3 - Cl O 1 2 PhMgBr...

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