OCHEM - Exam Three (Reactions of Alkenes)

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38 Terms

1
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free radical addition

HBr or HCl/H2O2, heat

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halogenation

Br2 or Cl2 or I2/ CCl4

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alkene --> halide ANTI

halogenation (Br2 or Cl2 or I2/ CCl4)

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alkene --> alcohol and halide (Markonikov rule, -OH to most stable, halide to least stable) ANTI

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hydrogenation
H2, Ni or Pt or Pd
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alkene --> alkane SYN
hydrogenation (H2, Pt)
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hydrohalogenation
HCl or HBr
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alkene --> halide (most stable carbocation (Markonikov rule))
hydrohalogenation (HCl or HBr)
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free radical addition
HBr or HCl/H2O2, heat
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alkene --> halide (least stable carbocation (anti-Markonikov rule))
free radical addition (HBr or HCl/H2O2, heat)
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hydration
H2O,H+/heat
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alkene --> alcohol (most stable carbocation (Markonikov rule))
hydration (H2O, H+/heat)
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oxymercuration-demercuration
Hg(OAc)2, H2O/NaBH4, KOH
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alkene --> alcohol (most stable carbocation (Markonikov rule)) does NOT go through rearrangement ANTI
oxymercuration-demercuration (Hg(OAc)2, H20/NaBH4, KOH)
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hydroboration
BH3 THF/H2O2, KOH
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alkene --> alcohol (least stable carbocation (anti-Markonikov rule)) SYN
hydroboration (BH3 THF/H2O2, KOH)
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halogenation
Br2 or Cl2 or I2/ CCl4
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alkene --> halide ANTI
halogenation (Br2 or Cl2 or I2/ CCl4)
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halohydrin
Br2 or Cl2 or I2/ H2O
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alkene --> alcohol and halide (Markonikov rule, -OH to most stable, halide to least stable) ANTI
halohydrin (Br2 or Cl2 or I2/ H20)
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epoxidation
MCPBA/ CHCl2
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alkene --> epoxide SYN
epoxidation (MCPBA/ CH2Cl2)
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cyclopropanation
CH2I2, Zn (Cu)
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alkene --> cyclopropane SYN
cyclopropanation (CH2I2, Zn (Cu))
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ozonolysis
O3
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alkene --> cleavage of double bond
ozonolysis (O3)
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KMNO4
cold KMNO4 or OsO4
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alkene --> alkane SYN/ANTI
KMNO4
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1,2 and 1,4 addition of HX
HBr or HCl and temperature
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HCl, -40 degrees C
1,2 product
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HCl, 45 degrees C
1,4 product
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kinetic controlled product
1,2 product (low temp)
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thermodynamic product
1,4 product (high temp)
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diels-alder (trans, ring)
NO REACTION
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free-radical halogenation
Br2/light OR NBS/light
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alkene --> halide (allylic carbon, carbon adjacent to double bond)
free-radical halogenation (Br2/light OR NBS/light)
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Markonikov
hydrohalogenation, hydration, oxymercuration-demercuration, halohydrin
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anti-Markonikov
free radical addition, hydroboration