Chemistry%20of%20Alkenes%20-%20Summary

Chemistry%20of%20Alkenes%20-%20Summary - trans)halohydrin...

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CHEM 227 Spring 2009 Dr. A. Schaefer Chemistry of Alkenes – Review/Summary Sheet Additions to Alkenes Add Reagent Regiochem Stereochem “H-X” H-Br, H-Cl, H-I Mark Mixed (C + ) “X-X” X 2 N/A Anti (trans) X “X-OH” X 2 , H 2 O Mark Anti (trans) X NBS (or NCS), H 2 O “H-OH” H 2 O, Acid (heat) Mark Mixed (C + ) 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 Mark Starts anti Hg OAc , then is mixed with NaBH 4 1. BH 3 -THF 2. H 2 O 2 , NaOH, H 2 O Non-Mark Syn (cis) Carbene CHCl 3 , NaOH, H 2 O N/A Syn (cis) (dichlorocarbene) CH 2 I 2 , Zn(Cu) N/A Syn (cis) (dihydrocarbene) “H-H” H 2 , Metal, R-OH solvent (such as Pd/C or Pt 2 O) N/A Syn (cis) O mCPBA N/A Syn (cis) Also from base on a (
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Unformatted text preview: trans-)halohydrin “OH-OH” OsO 4 , NMO N/A Syn (Cis) Trans-diol made from treatment of H 3 O + on epoxide Oxidation/Cleavage of alkenes C=C Reagent Result 1. O 3 2. Zn, H 3 O + Alkene carbons become carbonyls, yields aldehydes and ketones KMnO 4 , H 3 O + Alkene carbons become carbonyls, • if H is present on alkene carbon, becomes a carboxcylic acid • if 2H present, get CO 2 HIO 4 , H 2 O Cis-diols become carbonyls, yielding ketones, aldehydes • Dihydroxylation (OsO 4 , NMO), then treatment with HIO 4 is an alternative to ozonolysis...
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This note was uploaded on 07/30/2009 for the course CHEM 101 taught by Professor Williamson during the Spring '08 term at Texas A&M.

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