HWSet12Fl2005Ans

HWSet12Fl2005Ans - Homework Problem Set 12 Iverson...

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Homework Problem Set 12 Iverson CH310M/318M Due Wednesday, Dec. 7 Chemistry 310M Dr. Brent Iverson 12th Homework December 2, 2005 NAME (Print): _____________________________ SIGNATURE: _____________________________ Please print the first three letters of your last name in the three boxes
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Homework Problem Set 12 Iverson CH310M/318M Due Wednesday, Dec. 7 Score: _________
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Homework Problem Set 12 Iverson CH310M/318M Due Wednesday, Dec. 7 CH 3 O O O OH H 2 O H O O O OH O O PBr 3 Br O O CH 3 O O O OH 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 12 Iverson CH310M/318M Due Wednesday, Dec. 7 OH H 2 SO 4 OH Br 2 Br H O NaOH PCC OH ? H 2 SO 4 / H 2 O ? 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. A) 4 pts B) 7 pts h ν 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. OR 1) Hg(OAc) 2 2) NaBH 4 Recognize that because you do not lose any carbon atoms in this reaction (no ozonolysis) the aldehyde could only be produced through a PCC reaction of the correspongind primary alcohol Recognize that the starting material is an alkane, and the free radical halogentation reaction with Br 2 is the only reaction you can use with alkane starting materials. Recognize
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This note was uploaded on 09/13/2008 for the course CH 310M taught by Professor Iverson during the Fall '05 term at University of Texas.

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HWSet12Fl2005Ans - Homework Problem Set 12 Iverson...

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