MT2_Wi07 - NU, Winter 2007 MT2 Chem 210-2 1 1. (20 pts) For...

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NU, Winter 2007 MT2 Chem 210-2 1 1. (20 pts) For a and b, gives the IUPAC name of the products shown. For a-d, complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) Name____________________________ b) O 1) Br 2 , AlBr 3 2) Mg, Et 2 O 3) HC(O)H 4) H 3 O + work up 5) PCC 6) PhLi 7) H 3 O + work up 8) Swern’s reagent Name____________________________ c) heat A reaction will definitely happen d) S Hint: H 2 O is similar to H 2 S e) 1) 1 equiv mCPBA 2) TsOH, MeOH 3) HBr, ROOR 4) NaH
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NU, Winter 2007 MT2 Chem 210-2 2 2. Propose a curved arrow mechanism for the following reaction, showing every proton–transfer steps. S OH OH TsOH O S + H 2 O
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NU, Winter 2007 MT2 Chem 210-2 3 3) (20 pts) Propose a full curved-arrow mechanism for the following reaction. Br OMe Br O Mg, Et 2 O O OMe +
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NU, Winter 2007 MT2 Chem 210-2 4 4. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from 1,3-
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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MT2_Wi07 - NU, Winter 2007 MT2 Chem 210-2 1 1. (20 pts) For...

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