Organic Chemistry - Assignment 7 Answers

Organic Chemistry - Assignment 7 Answers - CHM 1320...

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1 CHM 1320 Assignment 7 Answers Note: Many questions 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. 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 0.05 eq. OsO 4 1 eq NMO 2 eq. KMnO 4 NaOH 0.05 eq. OsO 4 1 eq NMO 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 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 0.05 eq OsO 4 1 eq NMO 1) mCPBA 2) H 3 O + 1) NaOCH 3 2) OsO 4 , NMO mCPBA 0.05 eq OsO 4 1 eq NMO 1) mCPBA 2) H 3 O +
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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 O O O H O H O H O H this carbocation is stabilized by resonance O H O H O O H O O -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
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