310MHWSet9Fl10ans - Homework Problem Set 9 Iverson...

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Homework Problem Set 9 Iverson CH310M/318M Due Monday, Nov. 29 1 Chemistry 310M Dr. Brent Iverson 9th Homework November 19, 2010 NAME (Print): _____________________________ SIGNATURE: _____________________________ Please print the first three letters of your last name in the three boxes
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Homework Problem Set 9 Iverson CH310M/318M Due Monday, Nov. 29 2 Score: _________
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Homework Problem Set 9 Iverson CH310M/318M Due Monday, Nov. 29 3 Cl NaSH SOCl 2 OH SH MeSO 2 Cl H 2 CrO 4 O H 2 S O 4 OSO 2 CH 3 OH N a H 2 SO 4 SH C r PCC OH O CH 3 CO 3 H OH OH O H H H H H H O OH OH 3 H O O H H OH OCH 3 H H O OH OCH 3 OH OCH 3 NaOH OH OCH 3 OH OH OH OH racemic racemic racemic 1 ) s racemic racemic racemic syn addition anti addition Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. * Compare stereochemistry o m p e g i c h t y H 2 O
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Homework Problem Set 9 Iverson CH310M/318M Due Monday, Nov. 29 4 CH 3 O O O OH H 2 O H O O O OH O O PBr 3 Br O O 3 O O O O H O O O OH HO Pd° 1) OsO 4 2) NaHSO 4 / H 2 O 1. One of the major concepts of organic chemistry is that functional groups such as alkene pi bonds, alcohol groups, or alkyl halides generally react the same whether they are in simple molecules or extraordinarily complex molecules. Below are three examples of very complex molecules that were part of famous organic syntheses by EJ Corey, who was awarded the Nobel prize for his contributions to organic synthesis. Study the molecules and determine which functional groups were changed. Then, in the box over the arrows, indicate what reagents were used to carry out the transformation. DO NOT BE INTIMIDATED!!! YOU KNOW THIS CHEMISTRY even if you do not understand all there is to know about the structures of these complicated molecules. 3 pts each
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Homework Problem Set 9 Iverson CH310M/318M Due Monday, Nov. 29 5 2. These are synthesis questions. You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction because only predominant products can be used. All the carbon atoms of the product(s) must come from the starting material(s) shown. OH H 2 OH Br 2 Br H O NaOH PCC OH ? H 2 SO 4 / H 2 O ? A) 4 pts B) 7 pts h ! S N 2 Recognize that the product is the result of Markovnikov addition of water to propene. Propene can easily be produced from the starting alcohol through dehydration.
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310MHWSet9Fl10ans - Homework Problem Set 9 Iverson...

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