14C_s10_finalB

14C_s10_finalB - Chemistry 14C Spring 2010 Final Exam Part...

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Spring 2010 Final Exam Part B Page 1 Page 1 score = Thalidomide, sold as an antiemetic and sedative for ‘hysterial’ pregnant women in the later 1950’s, caused in thousands of birth defects. One thalidomide stereoisomer has the desired effects while another stereoisomer is teratogenic. Questions 1–7 refer to the structure of thalidomide. N N O O O H O Thalidomide 1. (8) Complete each statement by writing a number in the blank. (a) Thalidomide has ____________ sp 2 atoms. (b) Thalidomide has ____________ conjugated atoms. (c) ____________ atoms of thalidomide are involved in partial or full pi bonds. (d) The largest group of atoms that always lie in the same plane contains ____________ atoms. 2. (2) Circle the most likely color for thalidomide. Red Orange Yellow Green Blue Indigo Violet Colorless Cannot determine 3. (2) Complete this drawing of thalidomide so that all of its sp 3 stereocenters have R absolute configuration. If this is not possible write ‘not possible’. N N O O O H O 4. (6) Complete this statement by writing a number in each blank. Including the molecule drawn in question 3, thalidomide has ____________ stereoisomers. Of these, ____________ are enantiomers of other molecules and ____________ are diastereomers of other molecules. The antiemetic and teratogenic forms of thalidomide can be interconverted in the body by deprotonation and reprotonation. Questions 5–7 refer to this process. 5. (4) Draw in the box the most significant resonance contributor for the conjugate base formed by deprotonation of H a with EnzNH 2 (an enzyme). Include all lone pairs. N
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14C_s10_finalB - Chemistry 14C Spring 2010 Final Exam Part...

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