CH223 Exam 2 practice 13

CH223 Exam 2 practice 13 - CH223 Exam 2 practice 13

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CH223 Exam 2 practice 13 (Exam practice) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 0 out of 10 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 Be aware that for some of the multiple choice questions you only get 2 submissions - choose wisely! For the mechanism questions, be careful not to make any random pink dots by accidentally clicking in the active gray box - the random dot gets recorded in your answer coordinate string! The due date for this assignment is past. Your work can be viewed below, but no changes can be made. Request Extension 1. --/2.25 points Draw the skeletal structure of the indicated major organic product. Assume there is excess halogen and hydroxide ion in question (b) and (c). (a) CC(C)(C)C(=O)CCl (b) CH223 Exam 2 practice 13 http://www.webassign.net/v4cgirhshaw@ncsu/student.pl?t=2008120718. .. 1 of 7 12/7/2008 1:47 PM
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CC(Br)(Br)C(=O)C1(Br)CCCCC1 (c) CC(C)(C)C(=O)O Solution or Explanation (a) Under acidic conditions alpha monohalogenation occurs because the halogen slows down the first step which is the protonation of the carbonyl oxygen. (b) Under basic conditions all of the alpha protons are replaced by the halogen because each alpha halogen speeds up the next alpha deprotonation until all of the alpha protons are replaced by the halogen. Under hydroxide ion conditions, a multi-halogenated ketone will not be the major organic product. The hydrate will be the favored product. The question, however, is worded in such a way
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CH223 Exam 2 practice 13 - CH223 Exam 2 practice 13

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