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hydroboration reagents
1. BH3-THF
2. H2O2, OH-, H2O
1. BH3-THF
2. H2O2, OH-, H2O
what reaction are these reagents from?
hydroboration
hydroboration regiochemistry/stereochemistry
anti-mark, syn
which reaction?
hydroboration
oxymercuration reagents
1. Hg(OAc)2, H2O
2. NaBH4
1. Hg(OAc)2, H2O
2. NaBH4
what reaction are these reagents from?
oxymercuration
oxymercuration regiochemistry/stereochemistry
mark, anti (step 1 only)
which reaction?
oxymercuration
alkoxymercuration reagents
1. Hg(OAc)2, CH3OH
2. NaBH4
1. Hg(OAc)2, CH3OH
2. NaBH4
what reaction are these reagents from?
alkoxymercuration
alkoxymercuration regiochemistry/stereochemistry
mark, anti (step 1 only)
which reaction?
alkoxymercuration
acid-catalyzed hydration reactants
H2O, H2SO4
or H3O+
H2O, H2SO4
what reaction are these reagents from?
acid-catalyzed hydration
H3O+
what reaction are these reagents from?
acid-catalyzed hydration
acid-catalyzed hydration regiochemistry/stereochemistry
mark, unknown stereochemistry
which reaction?
acid-catalyzed hydration
Acid-catalyzed addition of an alcohol reagents
CH3OH, H+
CH3OH, H+
what reaction are these reagents from?
Acid-catalyzed addition of an alcohol
Acid-catalyzed addition of an alcohol regiochemistry/stereochemistry
mark, unknown stereochemistry
which reaction?
Acid-catalyzed addition of an alcohol
alkene addition reactions with Carbocation Rearrangement
Hydrohalogenation
Acid-catalyzed hydration
Acid-catalyzed addition of an alcohol
hydrohalogenation reagents
H-X (X is halogen)
H-X (X is halogen)
what reaction are these reagents from?
hydrohalogenation
hydrohalogenation regiochemistry/stereochemistry
mark, unknown stereochemistry
which reaction?
hydrohalogenation
Radical Addition of HBr reagents
HBr, ROOR
HBr, ROOR
what reaction are these reagents from?
Radical Addition of HBr
Radical Addition of HBr regiochemistry/stereochemistry
anti-mark, unknown stereochemistry
which reaction?
Radical Addition of HBr
halogenation reagents
Br2 or Cl2, CCl4
Br2, CCl4
what reaction are these reagents from?
halogenation (bromination)
halogenation regiochemistry/stereochemistry
N/A, anti
which reaction?
halogenation (bromination)
Cl2, CCl4
what reaction are these reagents from?
halogenation (chlorination)
which reaction?
halogenation (chlorination)
halohydrin formation reagents
Br2, H2O
Br2, H2O
what reaction are these reagents from?
halohydrin formation
halohydrin formation regiochemistry/stereochemistry
mark, anti
which reaction?
halohydrin formation
dihydroxylation reagents
OsO4, H2O2
or
KMnO4 (cold, dilute), OH-
OsO4, H2O2
what reaction are these reagents from?
dihydroxylation
KMnO4 (cold, dilute), OH-
what reaction are these reagents from?
dihydroxylation
dihydroxylation regiochemistry/stereochemistry
N/A, syn
which reaction?
dihydroxylation
hydroxylation reagents
1. mCPBA
2. H3O+
or
1. RCO3H
2. H3O+
1. mCPBA
2. H3O+
what reaction are these reagents from?
hydroxylation
1. RCO3H
2. H3O+
what reaction are these reagents from?
hydroxylation
hydroxylation regiochemistry/stereochemistry
N/A, anti
which reaction?
hydroxylation
epoxidation reagents
RCO3H or MCPBA
RCO3H
what reaction are these reagents from?
epoxidation
MCPBA
what reaction are these reagents from?
epoxidation
epoxidation regiochemistry/stereochemistry
N/A, syn
which reaction?
epoxidation
ozonolysis reagents (reductive workup)
1. O3
2. (CH3)2S or Zn, H2O
1. O3
2. (CH3)2S
what reaction are these reagents from?
ozonolysis (reductive workup)
1. O3
2. Zn, H2O
what reaction are these reagents from?
ozonolysis (reductive workup)
which reaction?
ozonolysis (reductive workup)
ozonolysis reagents (oxidative workup)
1. O3
2. H2O2
or
KMnO4 (hot, conc), H3O+
1. O3
2. H2O2
what reaction are these reagents from?
ozonolysis (oxidative workup)
KMnO4 (hot, conc), H3O+
what reaction are these reagents from?
ozonolysis (oxidative workup)
Which reaction?
ozonolysis (oxidative workup)
hydrogenation reagents
H2, Pd-C or Pt or Ni
H2, Pd-C
what reaction are these reagents from?
hydrogenation
H2, Pt
what reaction are these reagents from?
hydrogenation
H2, Ni
what reaction are these reagents from?
hydrogenation
hydrogenation regiochemistry/stereochemistry
N/A, syn
which reaction?
hydrogenation
cyclopropanation reagents
CH2I2, Zn(Cu)
or
CHCl3, NaOH (strong base)
CH2I2, Zn(Cu)
what reaction are these reagents from?
cyclopropanation
CHCl3, NaOH (strong base)
what reaction are these reagents from?
cyclopropanation
cyclopropanation regiochemistry/stereochemistry
N/A, syn
which reaction?
cyclopropanation