CH223 Exam 2 practice 19

CH223 Exam 2 practice 19 - CH223 Exam 2 practice 19 (Exam...

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Unformatted text preview: CH223 Exam 2 practice 19 (Exam practice) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 0 out of 15 Due: Monday, November 10, 2008 07:00 AM EST Description This assignment is for practice only. The grade will NOT be used in any calculation therefore you do not have to do this assignment if you do not want to do it. The key and solution will be delivered after your first submission. Instructions The due date for this assignment is past. Your work can be viewed below, but no changes can be made. Request Extension 1. --/1 points CH223 Exam 2 practice 19 http://www.webassign.net/v4cgirhshaw@ncsu/student.pl?q=2008120718... 1 of 11 12/7/2008 1:52 PM Draw the skeletal structure of the indicated species. CC(=O)CC(=O)c1ccccc1 CCCC(CCC(C)C)C(=O)OC Solution or Explanation LDA deprotonates each carbonyl alpha-C. 2. --/0.5 points CH223 Exam 2 practice 19 http://www.webassign.net/v4cgirhshaw@ncsu/student.pl?q=2008120718... 2 of 11 12/7/2008 1:52 PM Draw the skeletal structure of the major organic product. CCCC(=O)O Solution or Explanation Carboxylic acid synthesis: enolate, alkylate (some versions have this twice), saponify, acidify, decarboxylate, tautomerize. 3. --/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 (b) Major organic product B (compound of interest, not the by-product). CCCC(CC)(C(C)=O)C(=O)OCC (c) Major organic product C (compound of interest, not the by-product). CH223 Exam 2 practice 19 http://www.webassign.net/v4cgirhshaw@ncsu/student.pl?q=2008120718... 3 of 11 12/7/2008 1:52 PM 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....
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CH223 Exam 2 practice 19 - CH223 Exam 2 practice 19 (Exam...

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