Alkene Addition Reactions

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