CH223 001 HW 29

CH223 001 HW 29 - CH223 001 HW 29

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CH223 001 HW 29 (Daily) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 17 out of 17 Due: Monday, November 3, 2008 07:00 AM EST Description This assignment corresponds mainly to Lecture 29 and the DE presentation(s) which accompany it. Instructions The due date for this assignment is past. Your work can be viewed below, but no changes can be made. 1. 1/1 points Draw the skeletal structure of the indicated product. There is one equivalent of base used in DOCH 3 solvent in step 1. Assume no alcohol proton exchange with solvent during the acid workup. Product A CC(=O)C1CCC(C)(C)C1=O CH223 001 HW 29 http:[email protected]/student.pl?m=200812071. .. 1 of 14 12/7/2008 1:15 PM
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Product B CO[D] Solution or Explanation Acylation of ketones with esters. The nucleophilic alpha carbon will be the alpha carbon of the ketone. The ester carbonyl carbon is the electrophilic carbon. 2. 1.5/1.5 points Draw the skeletal structure of the indicated species below. (a) Major organic product A (compound of interest, not the by-product). CCOC(=O)C(CC)C(C)=O CH223 001 HW 29 http:[email protected]/student.pl?m=200812071. .. 2 of 14 12/7/2008 1:15 PM
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CCCC(CC)(C(C)=O)C(=O)OCC (c) Major organic product C (compound of interest, not the by-product). CCCC(CC)C(C)=O Solution or Explanation Ketone synthesis. (A) The ethoxide ion will deprotonate the carbon alpha to both carbonyls to form the enolate ion which will then react in an S N 2 reaction with the alkyl bromide. Alkylating the interior alpha carbon (B) The second equivalent of ethoxide ion deprotonate that same alpha carbon to form the enolate again which reacts with the second alkyl bromide to alkylate the interior alpha carbon a second time. (C) Saponification (followed by acidification) transforms the beta-keto ester into the beta-keto acid which is then subjected to thermal decarboxylation forming the ketone. 3. 1/1 points Draw the skeletal structure of the major organic product. CH223 001 HW 29 http:[email protected]/student.pl?m=200812071. .. 3 of 14
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This note was uploaded on 02/03/2009 for the course CH CH 102, 20 taught by Professor Ta,ta,sandberg during the Fall '08 term at N.C. State.

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CH223 001 HW 29 - CH223 001 HW 29

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