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Markovnikov
Alkene + HX

Antimarkovnikov
Alkene + HBr/ROOR

Markovnikov, OH
Alkene + H3O+

Markovnikov, OH (second one)
Alkene + 1)Hg(OAc)2, H2O/ 2)NaBH4

Antimarkovnikov, OH & H cys, + En
Alkene + 1.) BH3 * THF / 2.) H2O2, NaOH

Elimination
Alkene + H2/Pt

Br on both carbons, anti + En
Alkene + Br2

Br & OH groups, anti + En
Alkene + Br, H2O

OH groups, anti + En
Alkene + 1.) RCO3H / 2.) H3O+

OH groups, syn + En
Alkene + KMnO4/NaOH, cold

2 OH groups, syn + En
Alkene + 1.) OsO4 / 2.) NaHSO3, H2O

Oxidative cleavage
Alkene + 1.) O3/ 2.) DMS

1 dihalide
Results in Alkyne after 1.) xs NaNH2 2.) H2O

2 dihalide
Alkyne + xs HX

Alkene
Alkyne + HX

Ketone
Alkyne + HgSO4 or HgSO4, H2O

Aldehyde
Alkyne + 1) R2BH 2) H2O2, NaOH

trans major product dihalide
Alkyne + X2 (one equivalent)/CCl4

tetrahalide
alkyne + ex. X2/CCl4

Carboxylic acid + CO2
alkyne + 1) O3 2) H2O

internal alkyne
terminal alkyne + 1) NaNH2 2)RX

trans, internal alkene
internal alkyne + Na/NH3(l)

Alkane
internal alkyne + H2/Pt

2 Alkane
Internal alkene + H2/Pt

cis, internal alkene
internal alkyne + H2/ Lindlar’s cat.