Organic Chemistry: Synthetic Transformations

HBr, ROOR, hv

Break double bond, add Br Anti-Mark

PCC

Primary alcohol to aldehyde

KMnO₄

Secondary alcohol to ketone, or primary alcohol to carboxylic acid

1) Cold, dilute KMnO₄ 2) H₂O₂

Break double bond, syn addition of 2xOH

1) O₃ 2) Zn, acetic acid

Cleave double bond and add O to each

1) Hot KMnO₄ 2) H₃O+/H₂O

Cleave double bond, add O to each and OH to one

HX, cold, dark, no ROOR

Triple to double bond, add X Mark. Remove double bond and add X Mark

X₂

Triple to double bond, add 2xX (Br or Cl) Trans, break double bond add 2xX (Br or Cl) Trans

H₂O, H₂SO₄, HgSO₄

Triple bond to carbonyl Mark

NaNH₂

Alkyne to acetylide ion

H₂O, H₂SO₄

Nitrile to carboxylic acid

H-X or PBr₃

Replace alcohol with halogen

Ethanol and Heat

Alkyl halide to alkene (both E and Z!)

Acid and Heat

Alcohol to alkene (both E and Z!)

Cl₂ and hv

Add Cl to alkane, HCL

Br₂ (or NBS) and hv

Tertiary alkyl bromide, HBr

1) R-MgBr 2) H₃O+/H₂O

Carbonyl to alcohol and add R

1) R-MgBr 2) R-X

Carbonyl to ether, add R and R

1) LiAlH₄ or NaBH₄ 2) H₃O+/H₂O

Carbonyl to alcohol

1) Li 2) CuI

Make cuprate (carbanion)

1) Hg(OAc)₂, H₂O, THF 2) NaBH₄

Break double bond, add OH Mark

1) BH₃ / THF 2) H₂O₂, NaOH

Break double bond, add OH Anti-Mark (racemic) or Triple bond to =O Anti-Mark

MCPBA (or RO₃H)

Epoxide formation

1) RO- 2) dilute acid

Ring opening, add OH and OR Anti-Mark

H+, HOR

Ring opening, add OH and OR Mark

Br₂, HOR

Break double bond, add Br and OR Mark

H₂/Pt

Break double bond, add 2xH (cis only!) or break triple bond, add 4xH

H₂/Lindlar

Triple to double bond, Cis

Na/NH₃

Triple to double bond, Trans