spring 2003 M1 - Chem 118 C Spring 2003 First Midterm...

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Chem 118 C Spring 2003 First Midterm April 25, 2003 Instructor: Nambiar This exam contains six pagesand six problems. Please make sure that your copy contains all the six pages. If there is a problem, please let us know before you start answering. Please answer all questions. Name: I. D. # T.A. 1
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I. (30 pts). Draw the structure of the expected organic product(s) formedin the following reactions. Unless mentioned otherwise, youcan assume that all reagents arepresent in excess. If no reaction occurs, write "No Reaction". 1) R-CH2-CN 1. H+/H20 /~ -<;; -00- C H 0 0 2. CH2N2 1. CH3Li q If e --~ rTJ (Z- 2) R-COOH 2. H+/H20 1. RMgBr el+~ 3) CH3COBr 2. H+/H20 &;~..J)-"'~(~.t~~:~>~; H20/00C 4) C6Hs-CO- NH2 1.Mg 5) R-CH2Br 2. CO2 3. H+ I CH30H I L\ « NaOH/H20/A 6) NaOH I Br2 7) R-CO-NH2 1. [(CH3)2CH-CH2hAl H 8) R-CONH2 2. H+/H20 1. LiAlH4 H/>1- ~ C6HS-CONH2 9) 2. CH3-CO-CI -t (Z CH3NH2 ... -~. 0 10) R-COOCH3 2
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ll.(20 pts) Show detailed reaction mechanisms for the following reactions, showing the structure of the expectedproducts. j) N il 161"", A /J)/) 1. ~-fl> ttJt1~ ,~ ttU}IV~ + R-N=C=N-R R-COOH + R'NH2 -'7 ~"'3-&\-\ ~-qz-O"- b I -~ ~ ~- tJ-c-I\Jf+R
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