MT2_Wi06 - NU, Winter 2006 MT2 Chem 210-2 1 1. (20 pts) For...

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NU, Winter 2006 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) O H Do not use F-C alkylation or Corey House Name____________________________ b) OMe OMe NO 2 O 2 N Do not use F-C alkylation or Corey House Name____________________________ c) OH Br O O Cl NO 2 d) 1) CO, HCl, CuCl, FeCl 3 2) Zn(Hg), HCl 3) Cl 2 , FeCl 3 take the least hindered product 4) H 2 SO 4 , 2 equiv HNO 3 5) NaNH 2 , heat
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NU, Winter 2006 MT2 Chem 210-2 2 2. a) Draw the structure of the starting material in the reaction shown below (2 pts). If you do not know what it is, you can buy the structure from the proctor. O 1-phenyl-1,2-propanediol + H 2 O H 2 SO 4 b) (13 pts) Propose a curved arrow mechanism for the above reaction, showing every proton–transfer steps. c) 2-Phenylpropanal has a constitutional isomer, 1-phenyl-1-propanone. Draw the structure of 1- phenyl-1-propanone (1 pt).
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MT2_Wi06 - NU, Winter 2006 MT2 Chem 210-2 1 1. (20 pts) For...

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