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by: Carmela Kilback


Carmela Kilback
GPA 3.92

Forrest Michael

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Forrest Michael
Class Notes
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This 4 page Class Notes was uploaded by Carmela Kilback on Wednesday September 9, 2015. The Class Notes belongs to CHEM 237 at University of Washington taught by Forrest Michael in Fall. Since its upload, it has received 24 views. For similar materials see /class/192550/chem-237-university-of-washington in Chemistry at University of Washington.




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Date Created: 09/09/15
1 For each of the following compounds draw the carbocation intermediate you would expect from an El elimination reaction Which reaction will be faster OH H2804 gt gt intermediate maj or product OH H2804 gt gt g E H intermediate maj or product Which is faster The second 2 Ethynylestradiol drawn below is the active component of birth control pills a Identify all chirality centers in the molecule with arrows b How many total stereoisomers are possible HO 5 stereocenters 25 32 isomers HO 3 The Melanesian rhinoceros beetle uses 2butanol as a pheromone a Draw R2butanol as a Fisher projection CH3 HO H CHZCH3 b Pure R2butanol has a specific rotation of l4 The 2butanol isolated from the beetles has a speci c rotation of 70 What is the percent enantiomeric excess of the 2butanol isolated from the beetles enantiomeric excess 7l4 50 ee c What percentage of the 2butanol isolated from the beetles is R 25 4 Fill in the boxes with the appropriate reagents andor products When a product is asked for draw the major product only BI Z H20 OH ch OH SOC12 CI gt HBr Br H H2 gt PdC H 5 Name the following compounds including stereochemical descriptors O H O H JV 3 mgOH 2R3 S 3bromo 2butanol 3R4R 15hexadien34diol 6 Draw both products that you would expect to get from each of the following reactions QUIIIIII Br B r gtHj Brz 0 Br B r Are these products enantiomers diastereomers or neither diastereomers HBr Br Br Are these products enantiomers diastereomers or neither neither 7 Propose a synthesis of the following molecule from an alkyl halide of your choice Note a halide must be the only functional group in your starting material Draw all reagents and intermediates CI OH CI alkyl halide 8 If you perform the bromination of the following compound in methanol solvent you obtain a new compound Elemental analysis reveals that it only has bromine atom What is the structure of the new compound Be sure to draw the appropriate stereochemistry OCH3 BI Z 0 gt Br With this in mind how would you make the following compound in one step Br l 1311 l O HO 9 You isolate an unknown hydrocarbon A If you treat A with hydrogen and a catalyst A reacts with 2 molecules of hydrogen to form B Upon ozonolysis A yields the two products C and D Draw the original molecule A and its hydrogenation product B 103 O 2 Zn 0 gt H H O C D A H2 excess PdC


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