3580 Spring 2011_PSET 10 - O KOH, OEt O O O + O (3) Pick...

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Chemistry 3580 Spring 2011 Prof. William Dichtel Homework: Problem Set #10 Will not be collected; key will be posted on 4/18/11 Textbook Problems: Ch 22 (p 1106) 22.54, 22.57, 22.62, 22.65, 22.70(a and b), 22.72, 22.80(a, b, e), 22.81(a-f), 22.83, 22.85, 22.89 (1) Propose an efficient synthetic route to convert the starting material into the product. (2) Predict the products of the following transformations. OH O 1. PBr 3 (1 eq), Br 2 2. O 1. NaOMe (1 eq) 2. H 3 O + OH NEt 3 OCH 3 O Product A OK Br excess excess Product B NH 2 Cl O NEt 3 Product A 1. LiAlD4 2. H3O+ 3. - OH 4. Cl O NEt 3 Product B O O O NC O N O O
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(4) Draw rational arrow pushing mechanisms for the following transformations:
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Unformatted text preview: O KOH, OEt O O O + O (3) Pick which of the following compounds can be synthesized in high yield directly from an aldol addition, aldol condensation, or Claisen condensation. If a compound can be synthesized in high yield, draw the starting materials that would lead to the product. If a compound cannot be synthesized in high yield, briefly explain why not. O OH O OH H O O O O O OCH 3 O H O O O OEt O O CF 3 F F NaOEt (excess) 1. 2. Br CF 3 F F O O...
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This note was uploaded on 11/01/2011 for the course CHEM 3580 taught by Professor Sogah, d during the Spring '08 term at Cornell University (Engineering School).

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3580 Spring 2011_PSET 10 - O KOH, OEt O O O + O (3) Pick...

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