W03 problems3b key

W03 problems3b key - SCH 3 1. 2eq. NaNH 2 2. H 2 , Lindlars...

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H Problem Set 3 (Chapter 10 Alkynes II/ Organic Synthesis) TA: Danny Ng 1/27/2003 2. Provide the r e a g e n t s or p r o d u c t s for the following reactions. Pay attention to stereochemistry if applicable. 1. Sia 2 BH 2. H 2 O 2 , NaOH 3. K 2 Cr 2 O 7 , H 2 SO 4 O H O 1. BH 3 2. CH 3 COOH 1. BH 3 2. H 2 O 2 , NaOH 1. LDA 2. 1-bromopentane 3. BH 3 4. CH 3 COOD 1. Draw the structure for Di- sec -isoamylborane (sia) 2 BH B H 1. (Sia) 2 BH 2. H 2 O 2 , NaOH HgSO 4 , H 2 SO 4 H 2 O or 1. BH 3 -THF (excess) 2. H 2 O2, NaOH H H O O H D D H OH O
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OH O Br Br Br Br O Br Br SCH 3 O O OH OH TA: Danny Ng 1/27/2003 O r g a n i c S y n t h e s i s Propose a synthesis for each of the following compounds using reagents with 4 c a r b o n s or less. Propose a synthesis to accomplish the following transformation (racemic) 1. H 3 PO 4 2. BH 3 -THF 3. H 2 O 2 , NaOH 4. SOCl 2 , pyr. 5. Na +-
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Unformatted text preview: SCH 3 1. 2eq. NaNH 2 2. H 2 , Lindlars cat. 3. OsO 4 then NaHSO 3 4. HIO 4 5. H 2 CrO 4 Note: For synthesis problems there can be more than one correct answer. For example, the cleavage of the double bond after step 2 can be accomplished with O 3 . I Retrosynthesis Forward: 1. LDA 2. iodoethane 3. H 2 , Pd/CaCO 3 O O H 3 C I O H I Forward: OH 1. Butyllithium 2. 4-iodobutyne 3. NaNH 2 4. iodomethane 5. Br 2 , CCl 4 O Br Br Br Br Retrosynthesis H H H H O O I O I Retrosynthesis OH 1. LDA 2. 4-iodobutyne 3. NaNH 2 4. 1-iodopropane 5. H 2 , Pd O H H H H Forward:...
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W03 problems3b key - SCH 3 1. 2eq. NaNH 2 2. H 2 , Lindlars...

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