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Midterm1- 143B - Chemistry 143B Winter 2011 NAME Ima Key...

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Chemistry 143B Winter, 2011 Exam #1 (1-25-11) Total Points: 100 NAME: Ima Key PID: ____________________________ ID Checker Initials: _____________________ TA Name: ___________ ____________ USE INK FOR RECORDING ANSWERS (if using pencil, no re-grades will be allowed) 1. (30 points) An analog of tacrolimus, a powerful immunosuppressive agent that conrols the rejection of transplanted organs in human patients, is depicted below. Refer to this structure to answer the questions that follow. O N O O O OCH 3 OH H 3 CO OH H 3 CO OH 1 2 3 4 5 6 O O 7 8 9 10 3 pts each answer (12 points this page) *The approximate 13 C NMR shift of carbon #3 in ppm is: ca. 200-210 *The approximate IR stretching frequency of the bond between carbon #2 and #8 is: ca. 2000-2300 cm-1 and the strength of the peak is (circle one): weak *Which IR stretching frequency would have a higher wavenumber (circle)? carbonyl at carbon #6 carbonyl at carbon #9
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Fill in the following table regarding the proton NMR properties of this compound: 3 pts each answer (18 points for table) Proton(s) attached to carbon # approximate 1 H NMR shift in delta units 1 ca. 5-6 2 ca. 1.7-2 4 ca. 2.5
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