Midterm-2-140A Spring 08-Key

Midterm-2-140A Spring 08-Key - Chemistry 140A Spring, 2008...

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Chemistry 140A TOTAL POSSIBLE: 250 Spring, 2008 POINTS MISSED: - 0 Second Midterm Exam-250 points 5/27/08 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. (24 points) Tacrolimus (shown below) is familiar to you from Exam-1. Refer to this structure to answer the question that follows. O O N O O O O OCH 3 O H 3 CO OH H 3 CO OH H Tacrolimus 1 2 3 4 5 6 7 8 9 10 11 12 13 15 14 15 of the atoms in tacrolimus have been numbered. Of the numbered atoms, designate each atom as either non-chiral (wrote “NC”) or, if chiral, write the appropriate “R” or “S” designation of the numbered atom. (1 pt each-15 pts total) Atom # NC, R or S Atom # NC, R or S Atom # NC, R or S 1 R 6 R 11 R 2 S 7 R 12 S 3 S 8 S 13 R 4 R 9 R 14 R 5 NC 10 R 15 S
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The cyclohexane ring located in the southeastern quadrant of tacrolimus can be abbreviated as shown below (where “R” designates the remainder of the tacrolimus molecule). On the chair cyclohexane template provided, draw this six membered ring. Be sure to match the numbered carbons on the template with those of the planar drawing. (3 pts each chiral center; 9 pts total)
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Midterm-2-140A Spring 08-Key - Chemistry 140A Spring, 2008...

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