FinalKey - I. (40 points) Name _ Page 1 w08.F.p1 A....

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Name _______________________ Page 1 w08.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. Draw the products for each reaction - if stereoisomers form, draw all of them. Compound Y c) Provide the IUPAC name, including stereochemistry when needed, for Compound Y. (S)-1-ethyl-3-methylcyclobut-1-ene 4 4 (a) (b) 6 (a) Na / NH 3 H 2 (excess) Pt H H the one chiral center must be 3-D OR + enantiomer E Z (b) O SH LiH O S 1) B 2 H 6 2) H 2 O 2 /NaOH CH 3 S O O Cl N OH O CH 3 S O O O (S) S Two reaction schemes collide in the following synthesis. Provide the missing information as needed. balance the reaction equation H 2 Li K eq = 10 x Use your pka table to estimate the Keq for this reaction. X = 25 O O N H Cl C 10 H 18 SO 3 3 4 4 4 4 4 OCH 2 CH 3 OCH 2 CH 3 C O OOH Cl 13 C-NMR signals: 4 or 3S and Z is okay, too or 1-cyclobutene CH 3 CH 2 OH H 2 SO 4 (cat.) uncharged major product(s)
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Name _______________________ Page 2 w08.F.p2 II. (36 points) Crestor earned more than $1 billion dollars for the Astra-Zeneca Pharmaceutical Co. in 2006. It is used to lower LDL cholesterol levels. B. A. (a) Find and label all chiral stereocenters and the o n e double bond that requires a stereolabel. (c) Rank the lengths of BONDS A-D by listing them in order, if any bonds are the same length, circle them. no partial credit S R shortest longest C B D A 3 (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). Obs. geom (shape) sp3 sp2 sp2 bent bent Hybridization Electronic (VSEPR) geom. tetrahedral trig planar Trigonal planar Atom O 1 O 2 N trigonal planar tetrahedral sp3 tetrahedral C BOND C N N N S O O C OH HO O OH E N N N S O O C OH HO O O Crestor Crestor (b) Circle the bases that can remove the most acidic proton from Crestor with a Keq > 1000.
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FinalKey - I. (40 points) Name _ Page 1 w08.F.p1 A....

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