CHEM12B Midterm 1 (Epoxides & Alkenes)

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daynuhmay
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CHEM12B Midterm 1 (Epoxides & Alkenes)
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2013-02-07 04:05:42
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Epoxides Alkenes
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Epoxides Alkenes
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    • 1o alcohol -> aldehyde
    • mild oxidizing agent
    • 1. PCC, 2. CH2Cl2
    • 1alcohol -> carboxylic acid
    • strong oxidizing agent
    • CrO3, H2SO4, H2O
    • or
    • K2Cr2O7,H2SO4, H2O
    • carboxylic acid->1o alcohol
    • strong reducing agent
    • LiAlH4
    • aldehyde -> alcohol
    • mild reducing agent (only reacts w/ aldehydes & ketones)
    • NaBH4
  1. reagents that make -OH a good leaving group
    • 1) TSCl, pyr (replaces OH with OTS)
    • 2) SOCl2, pyr
    • 3) PBr(replaces OH with Br)
  2. NaH (2 functions)
    • 1) deprotonates OH to O-
    • 2) forms alkene at site of halogen (E2 rxn)
  3. under acidic conditions, attack occurs at the ____ hindered side
    MOST hindered
  4. under basic conditions, attack occurs at the _____ hindered side
    LEAST hindered
  5. nucleophilic acids (3)
    • 1) HBr
    • 2) HCl
    • 3) HI
  6. non-nucleophilic acids (3)
    • 1) HNO3
    • 2) H2SO4
    • 3) HClO4
  7. MgBr+-R-
    • Grignard reagent
    • strong base, carbon nucleophile
    • attacks less hindered side of epoxide
    • useful in adding hydrocarbons to a molecule
  8. LiAlH4 (2 functions)
    • 1) strong reducing agent (carboxylic acid -> alcohol)
    • 2) breaks open epoxide without adding anything to it
  9. form less substituted alkene with ____ bulky base
    • more 
    • eg: LDA
  10. dehydration (E1) rxn
    H2SO4, H2O, heat
    • hydrogenation
    • syn addition
    • H2, Pt catalyst
  11. dihalogenation of an alkene 
    1) 1st halogen forms a(n) ____
    2) 2nd halogen (or nucleophilic solvent) attacks ____ hindered side
    • 1) 3-membered ring across alkene double bond
    • 2) more hindered side
  12. Markovnikov's Rule
    H from reagent added to C (of alkene) w/ most H's
  13. 1. BH3
    2. 3H2O2, 3NaOH
    • hydroboration
    • adds H to more and -OH to least substituted side 
    • anti-Markovnikov addition (in syn fashion)
  14. 1. Hg(OAc)2, H2O
    2. NaBH4
    • oxymercuration-demercuration (reduction)
    • Markovnikov addition of H-OH (in anti fashion) -> OH added to more substituted side
  15. KMnO4, H2O, NaOH
    • dihydroxylation
    • syn addition of 2 -OHs across alkene
  16. 1. O3
    2) Zn, AcOH
    • ozonolysis
    • cleavage at alkene bond resulting in 2 aldehydes
  17. mCPBA (w/ an alkene)
    • epoxidation
    • formation of epoxide at site of C=C
    • attacks above and below
  18. H2SO4, H2O,  (added to alcohol)
    OH -> C=C
  19. H2SO4, H2O (added to alkene)
    OH added to more hindered side (Markovnikov addition)

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