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Finalckey - I(40 points Name Page 1 w09.F.p1 A Complete the...

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Name _______________________ Page 1 w09.F.p1 I. (40 points) Complete the following reactions as directed. Transformations requiring sequential experimental steps should be numbered appropriately. 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) Br 2 /CH 3 OH OCH 3 Br + enantiomer OK OH +KBr Br These products are _____________________ of each other structural isomers HI I H I H 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. Cl 2 Cl CH 2 Cl CH 2 Cl Cl These products are _____________________ of each other diastereomers (S) O (R) O C O O O H These products are _____________________ of each other enantiomers Cl (a) (b) (c) 1. B 2 H 6 2. H 2 O 2 /NaOH (R) (S) HO 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. H CH 3 OH H alone, as a single product * (ii) H H Compound Z with a diastereomer with an enantiomer with >1 other stereoisomer (i) 13 C-NMR: 6 signals (i) (ii) view 5 5 5 5 - 3 if wrong conformation -5 if wrong molecule consistent gets second correct 4 4 4 3 5 most stable conformation most unstable conformation H H 3 C H OH - 5 if not eclipsed -3 if wrong eclipsed
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Name _______________________ Page 2 w09.F.p2 II. (44 points) Salvinorin A is found in certain varieties of sage plants, including Salvia divinorum , a Mexican plant used by Mazatec shamans throughout history. This compound is so intensely psychoactive that several states (like Illinois in January 2008) have passed legislation to ban the plant. As always, consider closed shell resonance contributors and rational ring bond angles when you analyze this structure. B. A. (a) Find and label all the chiral stereocenters in Salvinorin A (c) Rank the lengths of BONDS A-D (all have different lengths). O O O O H H 3 C H CH 3 C O O CH 3 O C O H 3 C Salvinorin A S S S R R R R shortest longest C B D A 14 4 (d) 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).
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