7 - 9/17/2011 Give reactants and reagents that could be...

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Unformatted text preview: 9/17/2011 Give reactants and reagents that could be used to prepare 2-ethylhexan-1-ol. H C OH C Br C C H2 OH C C C H PCC C OH H Br C Br C OH C Br Library of Synthetic Reactions C H Pd/C H C C Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H C Li C O 1. C O 2. H2O C OH H2 C C C Li C OH C C C H PCC C OH H Br C Br 1. Cb O Ca Li Ca Cb OH 2. H2O C H Pd/C H Li Br C C C O Li Br C Li AB C D ? OH OH ? 1. C O 2. H2O 2-ethylhexan-1-ol Which bond is formed in this reaction? Give reactants and reagents that could be used to prepare 2-ethylhexan-1-ol. H AC OH C Br BC C C OH D C C OH H Br C Br C C Br H2 C E C H Pd/C H C C Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H C Li H PCC C F O ? OH C 1. C O 2. H2O C OH C C H Li Br C C Li C OH OH C H2 C C OH Ca Li C H Pd/C C H PCC C OH ? C O 1. C O H Br C Br 1. Cb O Ca Cb OH 2. H2O Li Br C Li OH 2. H2O 2-ethylhexan-1-ol OH C Br C C OH C C OH H Br C Br Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H C C Br H2 C Ca Li C H Pd/C H C C H PCC C C O 1. Cb O Ca Cb OH 2. H2O Br Li C C H C C What is the structure of the organolithium? Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H C B A Which reaction scheme would be used for the last step? Li C OH OH H2 Pd/C PCC C C C C C H C OH Li H C O C H Br 1. C O 2. H2O Br Li C C Br C C OH Li AB C D b a OH 1. C ?O 2. H2O ? OH 1. OH 2. H2O Which atom in the floral fragrance corresponds to "a"? 1 9/17/2011 Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H AC C Br BC C H C C OH OH H2 Pd/C C D C C E C H C C OH Li H PCC C O F C H Br 1. C O 2. H2O C C Li Br Br C C OH H AC C Br BC C C H2 Pd/C H C OH OH C C E C H C C OH Li H PCC Li What is the next D reaction? C C F O Br 1. C O 2. H2O Li Br C C Br C OH C Li Br Li 1. OH C H 2. H2O OH Li 1. Li 2. H2O 1. C OH O 2. H2O What is the next reaction in this synthesis? What is the next reactant in this synthesis? Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H AC C Br BC C H C C OH OH H2 Pd/C C D C C E C H C C OH Li H PCC C O F C H Br 1. C O 2. H2O C C C C C Br C C H OH C Li Br Br H C OH OH H2 Pd/C C C C H C C OH Li H PCC Li Which bond will be formed in this reaction? C C C O Br 1. C O 2. H2O C C Li Br Br C C OH Li Br Li 1. OH H 2. H2O OH Br Li 1. 2. H2O 1. C AB O OH C 2. H2O Br D What is the next reaction in this synthesis? What is the next reactant in this synthesis? 11 Propose a synthesis of the floral fragrance from compounds containing 4 carbon atoms or less. H AC C Br BC C C H C OH OH H2 Pd/C PCC C D C C E C H C C OH Li H C O F C H Br 1. C O 2. H2O Br Li C C Br C OH H C C Br C C H C C Li OH OH H2 Pd/C C Which bond will be formed in this reaction? C C C H C C OH Li H PCC C OH C O Br 1. C O 2. H2O Br Li C C Br C C OH Li Br Li 1. H 2. H2O OH 1. Li Br OH 2. H2O 1. C O OH 2. H2O OH What is the next reaction in this synthesis? What is the next reactant in this synthesis? OH 12 2 9/17/2011 H C C Br C C H C OH OH H2 Pd/C C C C C H H PCC C Propose a synthesis of C OH H Br the following compound 1. C O from compounds C Li C 2. H2O containing 4 carbon atoms or less. C O Br Li C Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. Br H C OH C Br C C C OH C Pd/C Li H Br Li 1. OH C H2 OH C Do you think you can work this problem? C C C A. Yes H H C OH H 1. C B. Maybe PCC C C C. No O Li C Br O 2. H2O C C Li Br Br C C OH Li 2. H2O A Which synthetic route is the best? + OH B + 13 H C C Br C C H C OH OH H2 Pd/C C C C C H H PCC C Propose a synthesis of C OH H Br the following compound 1. C O from compounds C Li C 2. H2O containing 4 carbon atoms or less. C O Br Li C Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. Br H C OH C Br C C C OH C H Br Li 1. OH C H2 Pd/C Li OH C 1. 1. Identify the appropriate reaction scheme. C C C H H PCC C C C OH Li 2. Draw the reactant as the product. C O H Br 1. C O 2. H2O C C Li Br Br C C OH Li 3. Modify the reactant to conform to the reaction scheme. 2. H2O A + OH B If your class ID ends in turn in your form for credit. + 14 H C C Br C C H C OH OH H2 Pd/C C C C C H Does the product of C OH H this synthesis occur in 1. C nature? C Li H PCC C Br C Br Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. Br H O 2. H2O O C Li C C OH C C Br C C C Li H OH 1. Li Br Use your quiz/workshop form for your answer C OH OH H2 Pd/C PCC C C C C C H C Li H C C O OH H Br 1. C O 2. H2O Br Li C C Br C C OH Li 2. H2O floral fragrance A C OH Thyme 15 B D 3 9/17/2011 Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. H C OH C Br C C Pd/C H C H2 OH C 1. Identify the appropriate reaction scheme. C C C H H PCC C C OH H Br C Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. H Br C OH C Br C Li 2. Draw the reactant as the product. C O 1. C O 2. H2O C OH C C Pd/C H Li Br C C Li C H2 OH C C C C C H C PCC C OH C Br C C H C H2 Pd/C OH C 1. Identify the appropriate reaction scheme. C C C H H PCC C C O H Br 1. C O C C 2. H2O Li Br Br C C OH Li + Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. C Li H 3. Modify the reactant to conform to the reaction scheme. H OH C OH H Br C Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. H Br C OH C Br C Li 2. Draw the reactant as the product. C O 1. C O 2. H2O C OH C C C Li C H2 Pd/C H Li Br C OH C C C C C H C OH Li H PCC C C O 3. Modify the reactant to conform to the reaction scheme. H Br 1. C O C C 2. H2O Li Br Br C C OH Li + OH Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. H C C Br C C H C OH OH H2 Pd/C PCC C 1. Identify the appropriate reaction scheme. C C C H H C C C Li C 3. Modify the reactant to conform to the reaction scheme. H Br C Br C C Br 2. Draw the reactant as the product. O OH Propose a synthesis of the following compound from compounds containing 4 carbon atoms or less. H 1. C O 2. H2O Br Li C C OH C C H C Li C OH OH H2 Pd/C PCC C C C C C H C Li H C C O + OH H Br 1. C O 2. H2O Br C C Li Br C C OH Li D + + B 4 9/17/2011 Some synthetic problems: Using the following reactions, propose syntheses for the following compounds from reactants containing four carbon atoms or less. O Br some solutions are at the end of these notes 25 26 5 ...
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