8487-Q-09B-KEY - Friday, April 1, 2011 Please PRINT CHM...

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Friday, April 1, 2011 CHM 2211-8487 Quiz #09 Form B Page 1 of 1 Please Last PRINT name: First name: UFID: ______ /20 pts. Put your answers in the spaces, or check R or insert your answer 1. ( 6 pts ) For the electrophilic aromatic substitution (EAS) reaction of N -phenylacetamide with HNO 3 /H 2 SO 4 : (a) Draw (complete) the most important contributing structure of the p -substituted cation intermediate . (b) Draw (complete) the structure of the resulting p -disubstituted benzene product . HN C HNO 3 , H 2 SO 4 HN COCH 3 H NO 2 HSO 4 (a) The most important contributing structure of the p -substituted cation intermediate. HN COCH 3 H 2 SO 4 (b) p -Disubstituted benzene product. NO 2 + O CH 3 – H 2 O _____ 2. ( 3 pts ) Arrange components A D in order of decreasing reactivity toward EAS. N H 3 C CH 3 CH 3 CH=O OH Cl B C A D > > > Most reactive > Least reactive B D C A _____ 3. ( 8 pts ) (a) Draw (complete) the product structure resulting from the EAS reaction of
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