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Hyrdrohalogenation

Markovnikov, H-X, adds a hydrogen and a halogen to an alkene, rearrangements possible

Acid-catalyzed hydration

Markovnikov, H2O and acid/H3O+, adds a hydrogen and OH group to an alkene, rearrangements possible

Oxymercuration-demercuration

Markovnikov, Hg(OAc)2, H2O and NaBH4, adds OH and hydrogen, rearrangements not possible

Hydroboration-oxidation

Anti-markovnikov, Bh3, THF, H2O2, NaOH, H2O, syn addition (basically like cis), adds an OH to an alkene, no rearrangements

Hydrobromination with Peroxides

Anti-markovnikov, HBr and ROOR, adds bromine and hydrogen to an alkene, no rearrangement

Halogenation

Anti-markovnikov, X2 where X is a halogen, adds halogens to alkenes to make a vicinal dihalide, anti-addition, no rearrangement

Halohydrin Formation

Markovnikov, X2 and H2O, adds OH and X to an alkene, anti-addition, no rearrangements

Hydrogenation

H2 and Pd/C, reduces an alkene to an alkane by adding hydrogens, syn addition, no rearrangements

Epoxide Formation

mCPBA, takes an alkene and turns it into an epoxide (basically a triangle shaped ether), syn addition, no rearrangements

Diol Formation (anti)

mCPBA and H3O+, takes an alkene and adds 2 OH’s, anti-addition, no rearrangements

Diol Formation (syn)

OsO4 and NMO, adds two OH’s to an alkene,syn addition, no rearrangements

Ozonolysis

O3, Zn, H3O+, DMS, turns an alkene into two carbonyls (like an aldehyde and a ketone)

Oxidative Cleavage

Diol formation then HIO4, H2O, same result as ozonolysis (aldehyde and ketone)

Cyclopropane Formation

CH2I2, Zn(Cu), takes an alkene and turns it into a cyclopropane, syn addition, no rearrangements

Hydrohalogenation (alkyne)

same as alkene

Acid-catalyzed hydration (alkyne)

produces an aldehyde??

Oxymercuration-demercuration (alkyne)

produces an aldehyde

oxymercuration-demercuration (terminal alkyne)

makes an aldehyde, markovnikov

hydroboration-oxidation (alkyne)

makes an aldehyde, syn addition

hydroboration-oxidation (terminal alkyne)

anti-markovnikov that makes a carboxylic acid, syn addition

halogenation

excess X2, turns an alkyne into an alkane with 4 X’s (wedge and dash on either side), anti addition, no rearrangment

dissolving metal reduction

Na, NH3, takes an alkyne and turns it into an alkene, anti addition and no rearrangements

hydrogenation with poisoned catalyst

H2 and lindlar catalyst, takes an alkene and reduces it to an alkene BUT it won’t reduce an alkene to an alkane, syn addition and no rearranegment

acetylide alkylation

NaNH2, primary alkyl halide, takes an alkene with a terminal hydrogen and changes it to having a terminal carbon? no rearrangements

dihalide elimination

strong base in excess, it will take a dihalide alkane and turn it into an alkyne using anti elimination, no rearrangments

hydrogenation (alkyne)

H2 and Pd/C, reduces alkyne to alkane, syn addition, no rearrangement