assignment 7 - CHM 1321 Assignment 7 1 Predict the major...

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CHM 1321 Assignment 7 1) Predict the major product(s) of the following reactions: a) b) c) 1-methylcyclohexene d) e) f) g) h) j) 1) O 3 2) PPh 3 1) O 3 2) CH 3 SCH 3 1) O 3 2) CH 3 SCH 3 1) O 3 2) CH 3 SCH 3 2 KMnO 4 NaOH OsO 4 mCPBA i) mCPBA mCPBA OsO 4
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2) Propose efficient methods to achieve the following transformations (some may require more than one step): a) b) c) d) OH OH OH OH Br OH OH O e) OH OH f) OH OH 3) Predict the outcome of the following: a) H 2 Pd/C b) H 2 Pd/C c) D 2 Pd/C 4) Account for the following observation by drawing a mechanism. What is responsible for the regioselectivity in this reaction? O H CH 3 OH OO 5) Compound A is a degradation product of the antibiotic vermiculine. The structure of A was confirmed by transforming A into B (C 11 H 18 O 4 ) which could also be prepared by the ozonolysis of C (C 11 H 18 O 2 ), a commercially available material. One mole of compound C reacts with 1 mole of bromine to give D (C 11 H 18 Br 2 O 2 ). Assign structures to compounds B , C and D .
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This note was uploaded on 10/24/2010 for the course SCIENCE 2776 taught by Professor Dr.alisonflynn during the Fall '10 term at University of Ottawa.

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assignment 7 - CHM 1321 Assignment 7 1 Predict the major...

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