FinalaKey - I. (40 points) Name _ Page 1 S09.F.p1 A....

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Name _______________________ Page 1 S09.F.p1 I. (40 points) Complete the following reactions as directed. Show the major organic product(s) unless otherwise specified. Abbreviations for reagents are not allowed. If a product forms as a stereoisomeric mixture, draw one and write "+enantiomer" or "+diastereomer" in the box. B. A. (a) (b) These products are _____________________ of each other diastereomers A mixture of exactly (and only) two different products forms in each of these reactions. For each reaction, draw both products clearly (showing stereochemistry when applicable) and describe explicitly the relationship between them. H 2 These products are _____________________ of each other diastereomers These products are _____________________ of each other diastereomers (a) (b) (c) Cl 2 /CH 3 OH (S) (R) Cl Compound Z forms: (check one) Draw Newman Projections for the most stable and the most unstable conformations of the bond indicated in Compound Z. You must view the bond as shown by the arrow. Electronic repulsions destabilize as much as steric crowding. H 3 CO CH 3 Cl H alone, as a single product * (ii) OCH 3 H Compound Z with a diastereomer with an enantiomer with >1 other stereoisomer (i) Thermodynamic product view 5 5 5 5 - 3 if wrong conformation -5 if wrong molecule consistent gets second correct 4 3 5 most stable conformation most unstable conformation OCH 3 H 3 C H Cl - 5 if not eclipsed -3 if wrong eclipsed 1) B 2 H 6 2) NaOH H 2 O 2 H 2 O CH 2 CH 3 H H CH 2 CH 3 Pt OH CH 2 OH OH CH 2 OH OH Cl OK OH O HO S O O CH 3 O OH 1) NaNH 2 2) CH 3 CH 2 I O (S) OCH 2 CH 3 NaI NH 3 Balance the reactions 5 3 1 1 3 stereo must be shown heat
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Name _______________________ Page 2 S09.F.p2 II. (40 points) Returning to the topic of swine flu, Zanamivir was one of the first neuraminidase inhibitors developed to treat the influenza virus. A. (a) Find and label all the chiral stereocenters and the C-C double bond in Zanamivir (b) BONDS 1-4 are all C-O bonds of different length - rank their lengths. Zanamivir S R shortest longest 3 4 1 2 13 5 (c) For each of the Atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic (VSEPR) geometry, and its observable geometry (shape). Obs. geom (shape) sp2 sp3 sp2 bent Hybridization Electronic (VSEPR) geom. Trigonal planar trig planar Tetrahedral/Td Atom O 1 O 2 N 1 trigonal planar BOND 4 BOND 3 BOND 1 Atom O 1 Bent sp2 Zanamivir N 2 bent trig or trigonal trig planar 2 2 2 2 O C O O H H HN HN HO HO HO C O NH 2 N H R R R Z O C O O H HN HN HO HO HO C O NH 2 N H 3pts Atom O 2 Atom N 1 Atom N 2
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This note was uploaded on 02/02/2012 for the course CHEMISTRY 210 taught by Professor Nolta during the Fall '10 term at University of Michigan.

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FinalaKey - I. (40 points) Name _ Page 1 S09.F.p1 A....

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