HW5KEY - fewer carbons. Br Br 2 , hv NaOC(CH 3 ) 3 CH 3 CH...

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CH 318N Spring 2007 Name: 1 Homework # 3 - KEY Due: TUESDAY 02-20-06* Please follow the HW Guidelines as posted on Blackboard. 1. Give the major organic product of the following reactions. Remember to identify stereochemistry, or write “+ enantionmer” as appropriate. H 2 , Pd/C H 2 , Lindlar catalyst 1. NaNH 2 , NH 3 2. 3. H 3 O + O Br OH Ni catalyst H H H OH OH
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CH 318N Spring 2007 Name: 2 2. Give the reagents or series of reagents needed to complete the following transformations. Several steps may be required, so start on scratch paper! OH CHCH 3 O O 1. MCPBA, CH 2 Cl 2 2. LiC CHCH 3 HgSO 4 H 2 SO 4 , H 2 O 1. BH 3 , THF 2. H 2 O 2 , -OH 1. Br 2 , Br - 2. NaNH 2 , NH 3 3. Lindlar catalyst
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CH 318N Spring 2007 Name: 3 3. Propose a synthesis of 1,2-dimethylcyclohexene (shown below) from cyclohexane. Several steps will be required, so please start on scratch paper. Br 2 , hv Br NaOC(CH 3 ) 3 CH 3 CH 2 OH MCPBA CH 2 Cl 2 O 1. BrMgCH 3 , ether 2. H 3 O + OH H 2 SO 4 , 170 o MCPBA CH 2 Cl 2 O 1. BrMgCH 3 , ether 2. H 3 O + OH H 2 SO 4 , 170 o
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CH 318N Spring 2007 Name: 4 4. Propose a synthesis of the following molecule starting from hydrocarbons of 3 or
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Unformatted text preview: fewer carbons. Br Br 2 , hv NaOC(CH 3 ) 3 CH 3 CH 2 OH HBr (CH 3 ) 3 COOC(CH 3 ) 3 Br NaNH 2 NH 3 NaC CCH 3 DMSO 1. Na, NH 3 2. H 3 O + MCPBA CH 2 Cl 2 NaNH 2 NH 3 NaC CCH 3 DMSO Lindlar catalyst OH OH OH O CH 318N Spring 2007 Name: 5 5. Propose a mechanism for the following reaction: Br Br HBr, 2eq. H Br Br Br H Br Br Br Br Br CH 318N Spring 2007 Name: 6 6. Propose a mechanism for the following reaction: O 1. BH 3 , THF 2. H 2 O 2 , -OH H B H H H B H H H B H H H 2 O 2 OH H OH O CH 318N Spring 2007 Name: 7 Recommended problems : Chapter 13 Exercises: 1, 4, 5, 6, 7, 9, 10, 12, 14, 15, 17, 18 Chapter 13 Problems: 21, 22, 28-34 (all), 36-41 (all), 43, 44, 46 *Note: The key to this HW assignment will be posted on Friday, February 16 to help you study for your exam on Tuesday. This is basically a free HW assignment, so take advantage of it!!...
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This homework help was uploaded on 04/15/2008 for the course CH 318N taught by Professor Willson during the Spring '08 term at University of Texas.

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HW5KEY - fewer carbons. Br Br 2 , hv NaOC(CH 3 ) 3 CH 3 CH...

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