MECHANISMS TO UPLOAD.txt

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Author:
pmmendez
ID:
46950
Filename:
MECHANISMS TO UPLOAD.txt
Updated:
2010-11-23 16:28:48
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MECHANISMS
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  1. ALKANE + X2
    • ALKYL HALIDE +HBr or HCl
    • (FREE RADICAL HALOGENATION)
  2. ALKENE + X2, CHCl3, CCl4
    • VICINAL DIHALIDE
    • ANTI ADD
    • (HALOGENATION)
  3. ALKENE + X2, H2O
    • VICINAL HALOGYDRIN
    • ANTI ADD. OH TO MORE SUBSTITUTED;
    • (HALOGENATION)
  4. ALCOHOL + HX
    • ALKYL HALIDE +H2O
    • SN1= 3o,2o. SN2= 1o, METHYL;
    • (SUBSTITUTION)
  5. ALCOHOL + PBr3
    • ALKYL BROMIDE + H2O
    • SN1= 3o,2o. SN2= 1o, METHYL;
    • (SUBSTITUTION)
  6. ALCOHOL +

    SOCl2, HCl, PCl5
    • ALKYL CHLORIDE + H2O
    • SN1= 3o,2o. SN2= 1o, METHYL
    • (SUBSTITUTION)
  7. ALKENE + HX
    • ALKYL HALIDE
    • MARK; X MORE SUBS. SHIFTS CAN OCCUR;
    • (ELECTROPHILLIC ADD OF HX)
  8. ALKENE +

    PEROXIDES (ROOR, ROOH, H2O2) AND HBr
    • ALKYL BROMIDE
    • ANTI MARK; X LESS SUBS;
    • (FREE RADICAL ADD OF HBr)
  9. ALCOHOL + H2SO4, H2PO4
    • ALKENE + H2O
    • E1= 3o,2o. E2= 1o;
    • (DEHYDRATION)
  10. ALKENE + DILUTE H2SO4 WITH H2O
    • ALCOHOL
    • MARK
    • (HYDRATION)
  11. ALKENE +

    1.B2H2, DIGLYME
    2. H2O2, OH-
    • ALCOHOL
    • ANTI MARK; SYN ADD
    • (HYDROBORATION-OXIDATION)
  12. ALKENE + H2 WITH Pt, Pd, Ni, Ru
    • ALKANE
    • INEFFICIENT FOR SYNTHESIS
    • (HYDROGENATION)
  13. ALKYL HALIDE+

    E1= 3o,2o, USE AN ALCOHOL.
    E2= 1o, USE STRONG BASE: NAOC(CH3)3/ HOC(CH3)3
    • ALKENE
    • (DEHYDROHALOGENATION)
  14. ALKENE +

    PEROXY ACID: CH3C=OOOH
    EPOXIDE + CARBOXYLIC ACID

    • SYN ADD
    • (EPOXIDATION)
  15. ALKENE +

    1.O3
    2. H2O, Zn OR (CH3)S
    • 2 carboxylic acids
    • (aldehydes or ketones)

    OZONIDE: INTERMEDIATE

    OZONOLYSIS
  16. ALKENE + CONCENTRATED H2SO4
    multiple alkenes

    (PRODUCES DIMER OR POLYMERS) POLYMERIZATION
  17. R - LG + M+Nu-
    • R-Nu
    • (M+LG-)

    NUCLEOPHILE SUBSTITUTION

    SN2: BACKSIDE ATTACK
  18. ALCOHOL +

    TOSYLATE CHLORIDE
    • alkyl tosylate
    • (HCL)

    FORMATION OF ALKYL TOSYLATE

    -OT IS LEAVING GROUP
  19. TERMINAL ALKYNE +

    NaNH2, NH3
    • alkyne anion (coj. base)
    • (NA+, NH3)

    FORMATION OF ALKYNE ANION
  20. ALYNE ANION +

    METHYL OR PRIMARY ALKYL HALIDE
    • alkyne
    • (LG-)

    • ALKYLATION
    • ALKYNEANION IS THE NUCLEOPHILE
  21. VICINAL DIHALIDE +

    1. 2NaNH2, NH3
    2. H2O
    • alkyne
    • (2NaX, NH3)

    • FORMATION OF ALKYNE
    • DOUBLE DEHYDROHALOGENATION
  22. ALKYNE + 2H2/ Pt, Pd, Ni OR Rh
    alkane

    HYDROGENATION
  23. ALKYNE + H2 / Lindlar Pd
    alkane

    • LINDLAR REDUCTION
    • syn addition
  24. ALKYNE + Na OR Li / NH3
    trans alkene

    • METAL AMONIA REDUCTION
    • free radical intermediates
  25. ALKYNE + HX
    alkenyl halide

    • HYDROHALOGENATION
    • mark
    • anti-mark when HBr + peroxides
  26. ALKYNE + 2HX
    geminal dihalide

    • HYDROHALOGENATION
    • mark
    • anti-mark when HBr and peroxides
  27. ALKYNE + X2
    vicinal dihalide - trans alkene

    • HALOGENATION
    • anti addition
  28. ALKYNE + 2X2
    tetrahalide

    HALOGENATION
  29. ALKYNE +

    1. H20 AND
    2. H2SO4, HgSO4 (or HgO)
    ketone

    • HYDRATION
    • mark, keto-enol tautomerism
  30. ALKYNE +
    1. 03
    2. H2O
    2 carboxylic acids

    OZONOLYSIS

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