CH223 001 HW 20

CH223 001 HW 20 - CH223 001 HW 20

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CH223 001 HW 20 (Daily) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 7.5 out of 12 Due: Monday, October 13, 2008 07:00 AM EDT Description This assignment corresponds mainly to Lecture 20 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. 1/3 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) O=C(CI)c1ccccc1 (b) CH223 001 HW 20 http://www.webassign.net/v4cgirhshaw@ncsu/student.pl?w=200812071. .. 1 of 6 12/7/2008 1:00 PM
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CC(C)(I)C(=O)C(C)(I)I (c) CC1(C(=O)O)CCCCC1 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
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CH223 001 HW 20 - CH223 001 HW 20

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