S.11.215E1KEYv2 - Name_ Page 1 S.11.215E1 I. (18 points) A....

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Name_____________________________ I. (18 points) Page 1 S.11.215E1 A. The reaction below is an example of an electrophilic aromatic substitution. Though the reagents may be unfamiliar to you, this reaction proceeds in the same manner as any other electrophilic aromatic substition you have encountered. In the two examples shown below, the researchers ( J. Org. Chem. , 68 , 5759) found that altering the substituent at R from -CH 3 to -Ph significantly increased the amount of para substituted product produced versus the ortho substituted product. O R Compound 1 O O S O O O (CF 3 SO 2 ) 2 O, CH 2 Cl 2 O R S O O O O O R S O O O O + 50% para substitution 50% ortho substitution R= CH 3 R = 82% para substitution 18% ortho substitution Explain, using words and pictures why the amount of para substituted product increases for the phenyl substituted starting material. O S O O O O O CH 3 S O O O O Steric interaction between the new substituent and the bulkier phenyl group decreases the proportion of ortho subsituted product in the phenyl case. (phenyl) (methyl) B. Sesterstatin 6 is being examined as an anti-cancer drug. Answer the following questions about the individual atoms indicated in Sesterstatin 6 by circling the correct answer in each box. O O H H H CH 3 HO CH 3 OH CH 3 OH CH 3 H 3 C Sesterstatin 6 stereochemistry: R or S hybridization: sp sp 2 sp 3 linear trigonal planar tetrahedral geometry: hybridization: sp sp 2 sp 3 stereochemistry: R or S stereochemistry: R or S The formula of Sesterstatin 6 is C 25 H 38 O 5 .
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This note was uploaded on 09/21/2011 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.

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S.11.215E1KEYv2 - Name_ Page 1 S.11.215E1 I. (18 points) A....

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