Organic Chemistry Synthesis Reaction

Alkene to Vicinal Dihalide

X2

Anti-Product

Alkene to Vicinal Diol

1) OsO4
2) NaHSO3

Syn-Product

Alkene to Alkane

H2 gas , Pd/Ni/etc.

Syn-Product

Alkene to Haloalkane

HX

Markovnikov
Carbocation Rearrangement

Alkene to Alcohol (Markovnikov, Carbocation Rearrangement)

H2O, Catalytic acid (H2SO4)

Alkene to Alcohol (Non Markovnikov)

1) BH3
2) H2O2, NaOH

Alkene to Alcohol (Markovnikov, no Carbocation Rearrangement)

1) HgOAc, H2O
2) NaBH4

Alkene to Ether

R-O-H, Catalytic Acid (H2SO4)

Markovnikov
Carbocation Rearrangement

Alkene to Aldehyde or Ketone

1) O3
2) (CH3)2S

Alkene to Halohydrin

H2O, X2

Markovnikov for the OH group

Vicinal Dihalide to Alkyne (internal)

2 moles NaNH2

Vicinal Dihalide to Alkyne (terminal)

1) 3 moles NaNH2
2) H3O+ (if no anion is wanted)

Alkyne to Geminal Dihalide

2 mol HX

Alkyne to Tetrahaloalkane

2 mol X2

Alkyne to Aldehyde or Ketone (Internal)

1) BH3
2) H2O2, NaOH*

Alkyne to Aldehyde or Ketone (Terminal)

1) (sia)2BH
2) H2O2, NaOH

Alkyne to Alkene (Syn-Product)

H2, Lindlar's Catalyst

Alkyne to Alkene (Anti-Product)

Na, NH3