140C midterm 1 key

140C midterm 1 key - Chemistry 140C Spring, 2009 First...

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Chemistry 140C TOTAL POSSIBLE: 250 Spring, 2009 POINTS MISSED: - 0 First Midterm Exam-250 points 4/20/10 TOTAL: 250 DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO. ....FILL OUT THE FOLLOWING INFORMATION NOW : . LAST NAME (Print): KEY FIRST NAME (Print): Ima PID: __________________________________________________ SIGNATURE: __________________________________________ ID checker initials: ____________________ If you wish to have any answers considered for a re-grade, your exam must be completed in INK .
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1. (63 points) For the following roadmap problem, draw the structure of the organic product or starting materials labeled A., B., etc. in the boxes provided on the following page. If a box is above an arrow (“C”), you are to provide the reagents necessary to effect the transformation. For this question, it is not necessary to provide a solvent for “C”. NaCN; DMSO IR: 3300 ; 1735 cm -1 PhCH 2 Br A IR: 2250 cm -1 1) NaOH / H 2 O 2) H 3 O + B C D IR: 1780 cm -1 when D is reacted with water, HCl is formed NH 3 PhCH 2 CONH 2 Br 2 ; NaOH H 2 O E PhCO 2 H 155 o C F LAH; THF G PhCO 2 CH 2 CH 3 1) DIBAL ; Tol -60 o C 2) H 3 O + H I NaCNBH 3 EtOH IR: 1680 cm -1 (20-23) (19-9c) (20-8c) (19-27a) (21-34c) (19-27e) (21-34f ) (21-34g) (21-41e)
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A B C D E F G H I Ph-CH 2 -CN 7 points each box Ph-CH 2 -CO 2 H SOCl 2 Ph Cl O Ph NH 2 Ph N H Ph O Ph N H Ph Ph H O Ph N Ph Ph
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2. (30 points) As we discussed in class, reaction mechanisms represent our attempt to rationalize the observed results of organic transformations. Oftentimes, more than one mechanism is possible to explain the observed outcome. In order to gain
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This note was uploaded on 01/23/2011 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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140C midterm 1 key - Chemistry 140C Spring, 2009 First...

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