Organic Chemistry - Assignment 7 Answers

Ho ho ccl 3 co 2 h nan 3 n 3 n 3 or 46 36 18 h 2 o h

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HO HO CCl 3 CO 2 H NaN 3 N 3 N 3 or 46 % 36 % 18% H 2 O H 2 O or S N 1 E1 H N 3 Removal of H gives E1 Addition of N 3 - gives S N 1 11) Propose a synthesis of the following using any starting materials containing no more than 6 carbons.
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8 O Retrosynthesis O OH O MgBr Synthesis MgBr O O MgBr OMgBr H O H MgBr H 2 O OH H OH 2 H mCPBA O 12) Determine the structures of compounds A through G . C C 5 H 8 O C 6 H 12 O D B C 6 H 10 OH HBr Br OH C 6 H 12 O A E C 5 H 9 Br O O F C 10 H 18 O O OH 1) CH 3 MgI 2) H 3 O + H 2 SO 4 heat H 2 Pd/C H 2 SO 4 heat G C 10 H 16 1) O 3 2) PPh 3 1) Mg 2) 3) H 3 O + mCPBA 1) CH 3 MgI 2) H 3 O + H 2 SO 4 heat
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9 13) Point out all of the flaws in the following incorrect Grignard reactions. a) 1) Mg 2) 3) H 3 O + H O OH b) Br O 1) Mg 2) 3) H 3 O + H O O OH c) O 1) CH 3 CH 2 MgBr 2) H 3 O + OH OH Br HO OH OH OH group in original material will give acid/base reaction with the Grignard C=O group in original material will react with the Grignard as it is formed OH group in original material will give acid/base reaction with the Grignard. This reaction will happen faster than the desired displacement process
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