chem 262 reaction mechanisms

alkene

HX

alkene

1) O3 2) DMS

alkene

1) OsO4 2) NaHSO3 H2O
or

KMnO4 NaOH, cold

alkene

1) RCO3H

2) H3O+

alkene

Br2, H2O

alkene

Br2

alkene

H2, Pt

alkene

1) BH3 * THF

2) H2O2 NaOH

alkene

H3O+

or

1) Hg(OAc)2 H2O

2) NaBH4

alkene

HBr ROOR

alkane

Br2, hv

alkyne

HX (1 eq)

alkyne

alkyne

H2SO4 H2O

HgSO4

alkyne

1) R2BH

2) H2O2 NaOH

alkyne

X2 (1 eq)

alkyne

xs X2

alkyne

1) O3

2) H2O

alkyne

1) NaNH2

2) RX

alkyne

Na NH3 (l)

alkyne

H2 Pt

alkyne

H2 Lindlar’s cat

image to alkyne

1) xs NaNH2

2) H2O

image to alkyne

1) xs NaNH2

2) H2O

alkyne

xs HX

OH

conc H2SO4 heat

or

1) TsCl py

2) t-BuOk

ketone

1) LiAlH4

2) H3O+

OH

H2CrO4

or

PCC CH2Cl2

ROH (any degree) → RBr

HBr

ROH (any degree) → RI

HI

ROH (any degree) → RCl

HCl ZnCl2

ROH (1-2 degree) → RX

1) TsCl, py

2) NaX

ROH (1-2 degree) → RBr

PBr3

ROH (1-2 degree) → RCl

SOCl2, py

ketone (w/ Oh and Et)

1) MeMgBr

2) H3O+