Appropriately label the products as either achiral or

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Appropriately label the product(s) as either achiral or a racemic mixture. 1. O 3 2. Me 2 S Chem 33, Kanan & Stack, 2012, PS 9; pg 4
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O S O O CH 3 OAc H 3 C CH 3 H 3 C CH 3 HO OH CH 3 Br H 3 CO H 3 CO OH H 3 C CH 3 OH H 3 C CH 3 CH 3 CH 3 stereochemistry! 8. Provide the necessary reagents for the following transformations. H 3 C CH 3 HO OH H 3 CO OH CH 3 CH 3 Chem 33, Kanan & Stack, 2012, PS 9; pg 5
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Br 2 H 2 O NaH Et 2 O OsO 4 , NMO LiN i Pr 2 Et 2 O Cl OH O S O O CH 3 CH 3 KO t Bu t BuOH Cl H 1. BH 3 •THF 2. NaOH H 2 O 2 cat. H 2 SO 4 O OPh H 1. BH 3 •THF 2. NaOH H 2 O 2 CH 3 9. Predict the major product(s) from the following reactions. Show stereochemistry where applicable. O CH 3 1 equiv. HI t Bu CH 3 OH mCPBA Chem 33, Kanan & Stack, 2012, PS 9; pg 6
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a. Compound A (C 7 H 15 Br) is not a primary alkyl bromide. It yields a single alkene (compound B) on being heated with sodium ethoxide in ethanol. Hydrogenation of compound B yields 2,4-dimethylpentane. Identify compounds A and B. b. The three products shown below were formed when an unknown compound was treated with O 3 followed by a reductive work-up. Identify the the starting material.
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  • Spring '10
  • Dunremember
  • Chemistry, H3C, Chemical compound, Isomer, Chemical structure, 13C NMR resonances

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