assignment 7 answers - CHM 1321 Assignment 7 Answers Some...

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1 CHM 1321 Assignment 7 Answers Some questions may have more than one answer. For most questions, only one possible solution is presented. If you are not sure if one of your answers is correct please check with your TA or myself. 1) Predict the major product 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 mCPBA i) mCPBA mCPBA O O O O O O + + + O O O O 2 OH OH OH OH HO HO OH OH HO HO + OH OH O O O OsO 4 OsO 4 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 1) mCPBA 2) H 3 O + 1) NaOCH 3 2) OsO 4 mCPBA 1) mCPBA 2) H 3 O + OsO 4 OsO 4
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2 3) Predict the outcome of the following: a) H 2 Pd/C b) H 2 Pd/C c) D 2 Pd/C D D 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 O H O H OH O H this carbocation is stabilized by resonance O H O H H -H not formed or 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. Compound C reacts with 1 equivalent of bromine to give D (C 11 H 18 Br 2 O 2 ). Assign structures to compounds B , C
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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 answers - CHM 1321 Assignment 7 Answers Some...

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