DAT OChem Reactions

HBr

HBr

Br2

CCl4

HBr

ROOR

anti-mark

H3O+

H3O+

Br2

H2O

Hg(OAc)2 , H2O

NaBH4

BH3, THF

H2O2, OH-, H2O

OsO4

H2O2

KMnO4 (cold dilute)

OH-

RCO3H

H3O+

CH3OH

H+

Br2

CH3OH

Hg(OAc)2, CH3OH

NaBH4

RCO3H or MCPBA

H2, Pd/C

O3

(CHs)2S or Zn/H2O

O3

H2O2

or

KMnO4/heat

H3O+

H2

Pd/C

H2, Lindlar's catalyst

Na or Li

NH3(l)

1 eq HBr

1 eq HBr

1 eq HBr ---> 2nd eq HBr

1 eq Br2

HgSO4, H2SO4

HgSO4, H2SO4 -> Oxygen is added Markovnikov & HgSO4 is the catalyst because the reaction is so slow

Sia2BH, THF

H2O2, OH-, H2O

NaNH2

NaNH2

NaNH2

O3

H2O2

or

KMnO4/heat

H3O+

O3

H2O2

or

KMnO4/heat

H3O+

Br2

hv or heat

markovnikov

Cl2

hv or heat

NBS, hv or heat or ROOR

NBS, hv or heat or ROOR

hv or heat

hv or heat

hv or heat

hv or heat

hv or heat

CH3CH2MgX, Ether

H3O+

CH3CH2MgX, Ether

H3O+

2 eq. CH3CH2MgX, Ether

H3O+

2 eq. CH3CH2MgX, Ether

H3O+

CO2, ether

H3O+

CH3CH2MgX, Ether

H3O+

CH3CH2MgX, Ether

H3O+

CH3CH2MgX, Ether

H3O+

CH3CH2MgX, Ether

H3O+

CH3CH2Cl, AlCl3

CH3CH2CH2Cl, AlCl3

ClCOCH3

AlCl3

Br2

FeBr3

Cl2

FeCl3

HNO3

H2SO4

SO3

H2SO4

H2SO4/ heat

CO, HCl

AlCl3

substituent also o/p director =edg

substituent (M = EWG because those code for meta)

R-Cl or ClCOR

AlCl3

R-Cl or ClCOR

AlCl3

KMnO4, OH-

H3O+ / heat

or

Na2Cr2O7

H2SO4

KMnO4, OH-

H3o+, heat

or

Na2Cr2O7

H2SO4

H2NNH2 or N2H4, OH-,heat

Zn(Hg), HCl, Heat

Zn(Hg), HCl, Heat

CH3COOOCCH3

pyridine

NaBH4, EtOH

H3O+

LAH, EtOH

H3O+

NaBH4, EtOH

H3O+

LAH, EtOH

H3O+

LAH, EtOH

H3O+

LAH, EtOH

H3O+

DiBAL-H, -78

H2O

LAH, EtOH

H3O+

LAH (OC(CH3)3)3

LAH, EtOH

H3O+

Br2

NaOH

takes out the carbon with a double bonded O on it

LAH, EtOH

H3O+

HX

HX

PBr3

PBr3

SOCl2, pyridine (or PCl3 or PCl5)

SOCl2, pyridine

TsCl

H3O+

Na2Cr2O7 or CrO3

H2SO4

Na2Cr2O7 or CrO3

H2SO4

Na2Cr2O7 or CrO3

H2SO4

PCC or DMP

PCC or DMP

HIO4

HIO4

NaH, Na, or K

HBr

HBr

HBr