Practice Problems for Final Part 1 UPDATED

Practice Problems for Final Part 1 UPDATED - Practice...

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Practice problems – April 2011 Chem 3a, Spring 2011 Prof. Carolyn Bertozzi 1. Reaction of the following diol with one molar equivalent of benzyl bromide produces a 2:1 ratio of benzyl ethers A and B , respectively. By contrast, reaction of the same diol with t -butyldimethylsilyl chloride (TBDMSCl) produces silyl ethers C and D in a ratio of 10:1, respectively. a. Explain the difference in product ratios observed upon formation of the benzyl ether vs the silyl ether. What factors account for the major product observed in each reaction? b. Design a silyl ether protecting group that would display an even greater preference for product C.
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starting material to the given product using any reagents of your choice. Show each individual step in your synthesis and the intermediate obtained from that step. You might find it useful to work backward in the “retrosynthetic” sense on scratch paper before formulating your synthesis in the forward direction. Hint: some of these syntheses might require the use of more than one protecting group. a.
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This note was uploaded on 09/07/2011 for the course CHEM 3A taught by Professor Fretchet during the Spring '08 term at University of California, Berkeley.

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Practice Problems for Final Part 1 UPDATED - Practice...

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