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CH223 Exam 2 practice 14

CH223 Exam 2 practice 14 - CH223 Exam 2 practice 14...

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CH223 Exam 2 practice 14 (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 Make sure you check the number of submissions for each question. Multiple choice - 1 submission, fill in the blank - 2 submissions, JME - 3 submissions. The due date for this assignment is past. Your work can be viewed below, but no changes can be made. Request Extension 1. --/0.75 points Draw the skeletal structure of the most stable aldol condensation product from the reaction below. CC1=CC(=O)CC1 Solution or Explanation This is the intramolecular aldol addition-condensation reaction which gives either a 5-membered or 6-membered ring (depending on your version). One of the methyl alpha-carbons is deprotonated forming the nucleophilic carbon that attacks the other carbonyl carbon at the other end of the chain. 2. --/1.5 points CH223 Exam 2 practice 14 http://www.webassign.net/[email protected]/student.pl?j=2008120718... 1 of 8 12/7/2008 1:49 PM
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Draw the skeletal structure of the indicated species. (a) The organic starting material you need to carry out the reaction above. CC(=O)C1CCCCC1C(C)(C)C=O (b) The major aldol addition product. CC2(C)C(O)CC(=O)C1CCCCC12 Solution or Explanation This is the intramolecular aldol addition of a ketone (which becomes the enolate that attacks) and an aldehdye (which is the carbonyl that is attacked). 3. --/0.75 points Draw the skeletal structure of the major organic product which contains the carbon that originally was the carbonyl carbon formed from the reaction below. CCCCC1CCC(=O)C1 CH223 Exam 2 practice 14 http://www.webassign.net/[email protected]/student.pl?j=2008120718... 2 of 8 12/7/2008 1:49 PM
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Solution or Explanation This is a way to alkylate via 1,4 addition.
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