Ochem All Reactions

Hydride Shift

• H2O

Sn2

*flips s/r

• Nu:Na

• acetone

Sn1

• H2O

E2

• t-BuOK

E2

• H2O

Methyl Shift

*Markovnikov

• HBr

Electrophile Reaction

*Anti-Addition

• Br2

Electrophile Reaction

*Anti-Addition

• Cl2

• H2O

Hydroboration

*Anti-Markovnikov

*Syn-Addition

• BH3

Hydroboration Oxidation

• H2O2

Dehydration

*Syn-Addition

• OsO4

• H2O

Epoxidation

*Syn Addition

• RCO3H

Ozonation

• O3

Reaction of Alkenes

*Syn Addition

• H2

• Pd

Radical + Alkenes

• Br2

• Dark

Radical Halogenation of Alkenes

• Br2

• NBS

• Light

Radical Addition of Alkenes

*Markovnikov

• HBr

Radical Addition of Alkenes

*Non-Markovnikov

• HBr

• Peroxides

Alkynes + Strong Base

*Syn

• Br2

• NaH2 (Strong base)

• H2O

Alkyne + Lindt Catalyst

*Syn Addition

• H2

• Lindt Catalyst/Poison Catalyst

Alkyne + 1mol Halogen

*Anti Addition

• Br2 (1mol)

Alkyne with NH3 Liquid

*Anti Addition

• Na

• NH3 (Liquid)

Alkyne w/ H2SO4 or HgSO4

*Markovnikov

• H2SO4 + H2O

• HgSO4

Alkyne

*Non-Markovnikov

• BH3, THF

• H2O

Sn2

*Flips S/R (where H is)

• NaOH

• DMSO

*Syn Addition

• OsO4

• NaHSO3, H2O

2* Alcohol Sn2

*Flips S/R (where H is)

• SoCl2, PBr2

• Pyridine

1* Alcohol

• HBr or HCl

Formation of Dbl. Bond

• H2SO4

• Heat

• TsCl

• Pyridine

Makes aldehyde

Primary Alcohol

• PCC

• CH2Cl2

• H2CrO4

• Na

• NH3

Makes Carboxylic Acid

Primary only

• IBX

• DMSO

• PBr3/SoCl2