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HBr
Hydrohalogenation
H2SO4, H2O
Acid Catalyzed Hydration (or Hydration)
Cl2 or Br2
Halogenation
X2, H20
Halohydrin Formation
1) Hg(OAc)2, H2O
2) NaBH4
Oxymercuration-Reduction
1. BH3, THF 2. H2O2, NaOH
Hydroboration-Oxidation
OsO4
Dihydroxylation
(1) O3; (2) S(CH3)2
Ozonolysis
addition of hydrogen and metal catalyst
(H2, Pd)
Hydrogenation
NaOCH3
E2
H2O
SN1
NaNH2
alkyne deprotonation
H2O, HgSO4, H2SO4
oxymercuration of alkynes
NaCN
SN2
Cl2 MeOH
Halohydrin Formation
draw acid-catalyzes dehydration reaction
check
H2, Lindlar (cat.)
alkyne to alkene
t-BuOK
E2, side group to alkene
TsCl (or MsCl), pyridine (or Et 3N)
conversion of OH to OTs or OMs
PBr3
SN2
PCC
oxidation of alcohols
H2CrO4
oxidation of alcohols (creates carboxylic acid)
NaNH2 (on side group, no alkyne)
removes hydrogen
X 2 (Br2 or Cl2), heat or light
halogenation of alkanes
mCPBA
epoxidation of alkene
HBr, Peroxides
hydrohalogenation; anti-markovnikov
draw halohydrin formation reaction
check
HCN
Cyanohydrin Formation
NBS, light
allylic bromination
CH3OH, H2SO4
epoxi to OCH3
give the structure of the product of oxidative cleavage of cis-1,2-cyclopentanediol with HIO4. Draw both the starting material and the product
check
NaOH
strong base, E2
give the structure of the product of oxidative cleavage of cis-1,2-cyclopentanediol with HIO3. Draw both the starting material and the product
check