CH223 001 HW 36 - CH223 001 HW 36...

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CH223 001 HW 36 (Daily) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 16.5 out of 18 Due: Friday, November 21, 2008 07:00 AM EST Description This assignment corresponds mainly to Lecture 36 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 species Please review input instructions for the NO 2 group in the link below. a) Draw the reactant containing the aromatic ring. Brc1ccc([NO2])cc1[NO2] CH223 001 HW 36 http://www.webassign.net/[email protected]/student.pl?m=200812071... 1 of 14 12/7/2008 2:11 PM
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b) Draw the other reactant. C1CCNCC1 Solution or Explanation This is an NAS reaction addition-elimination. The aromatic ring will be the electrophile which means it will need to be electron poor. The 2 nitro groups make for a good electrophilic ring. The nucleophile is the amine. 2. 0.5/0.5 points You need to synthesize para -aminophenyl para -nitrophenyl ether. You realize that nucleophilic aromatic substitution is the synthetic route you are going to take. a) Select the two reagents you are going to need to carry out this NAS reaction. (Select two from the list below). para- fluoroaniline sodium para- aminophenoxide CH223 001 HW 36 http://www.webassign.net/[email protected]/student.pl?m=200812071... 2 of 14 12/7/2008 2:11 PM
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para -fluoronitrobenzene sodium para- nitrophenoxide b) Select the nucleophilic reactant. sodium para- nitrophenoxide sodium para- aminophenoxide para -fluoronitrobenzene para- fluoroaniline Solution or Explanation The practical synthetic route is to have an electron-rich nucleophile (the aminophenoxide ion) and an electron-deficient electrophile (the nitrofluorobenzene). 3. 1.75/2 points This question deals with nucleophilic aromatic substitution. The correction marks will not be shown for parts c and d. a) Draw the major organic product formed with para -bromonitrobenzene reacts with sodium ethoxide under heated conditions. Please see JME input instructions concerning nitro group (NO 2 ) input.
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