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addition reactions of alkenes (HCl, HBr, HI)
Addition of HCl, HBr, HI Markovnikov regiochemistry occurs, with adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.
addition reactions of alkenes (Cl2, Br2)
Anti addition is observed through a halonium ion intermediate.
addition reactions of alkenes (halohydrin formation)
Markovnikov regiochemistry and anti stereochemistry occur.
addition reactions of alkenes (oxymercuration-demercuration)
Markovnikov regiochemistry occurs.
addition reactions of alkenes (hydroboration-oxidation)
Non-Markovnikov syn addition occurs.
addition reactions of alkenes (Catalytic hydrogenation)
Syn addition occurs.
addition reactions of alkenes (epoxidation)
with a peroxyacid; Syn addition occurs
addition reactions of alkenes (Hydroxylation with OsO4)
Syn addition occurs
addition reactions of alkenes (Addition of carbenes to yield cyclopropanes: Dichlorocarbene addition)
Dichlorocarbene addition
Simmons-Smith reaction
Hydroxylation by acid-catalyzed epoxide hydrolysis
Anti stereochemistry occurs
Oxidative cleavage of alkenes (ozone, zince)
Reaction with ozone followed by zinc in acetic acid
Oxidative cleavage of alkenes (KMnO4)
Reaction with KMnO4 in acidic solution
Cleavage of 1,2-diols
Cleavage of 1,2-diols
dehydrohalogenation
alkyl halide + strong base
dehydration
alcohol + strong acid
halogenation
add Br or Cl
→ gives anti sterochemitry
halohydrins
alkene + HOX
→ DMSO or NBS solvent
hydration
water + alkene = alcohol
→ need high temps
oxymercuration-demercuration
alkene + Hg(OAc)2 = alcohol
→ follows Markovnikov rule
hydrobromination
alkene + BH3
→ non Markovnikov
hydrogenated
alkene + H2 + metal surface = saturated alkane
epoxide reaction
halohydrin + base = epoxide + HX
→ makes a ring
hydrolysis
epoxide + water = glycol
epoxycycloalkane and acid
epoxycycloalkane + acid + water = trans-1,2-diol
epoxycycloalkane and OsO4
epoxycycloalkane + OsO4 = cis-1,2, diol
ozone + tetra substituted double bond =
keytone + keytone
ozone + tri substituted double bond =
keytone + alcohol
disubstituted double bond
aldehyde + aldehyde
periodic acid reactions
adds a carboxyl group
carbene reaction
forms a cycloalkane
Simmons-Smith Reaction
the reaction of an alkene with CH2I2 and Zn-Cu to yield cyclopropane