Orgo Reactions

Alcohol hydration ROH

Strong aqueous acid (H₂SO₄)

ROH alcohol or ROR ether

oxymercuration

1. Mg(OAc)₂ , H₂O or ROH

2. NaBH₄

ROH (antim-arkovnikov)

1. BH₃ , THF

2. H₂O₂ , OH^-

Alkyne —> Alkene (cis)

H₂ Lindlar Catalyst

Alkyne —> Alkene (trans)

1. Na (s)

2. NH₃

Ether

Grignard reagent

Mg + R

Cyclopropane rings

Simmons Smith reagent (I… ZNI)

Remove 2* and 3* alcohol

dehydration

H+, H₂O

Remove 1* and 2* alcohol

dehydration with tosylate

TsCl or TsOH —> oTs is removed with NaBr

Halogenate 3* alcohols

H-Br, H-Cl

Halogenate 2* and 1* alcohols

SOCl₂ or Ph₃PBr₂

Alcohol —> Aldehyde

1* alcohol oxidation with chromic acid Na₂Cr₂O₇, H₂SO₄

Alcohol —> Carboxylic acid

1* alcohol oxidation with Swern (DMSO)

ROR’ ether

RX or ROTs + R’O^-

Alkene —> epoxide

PBA or MCPBA, CH₃CO₃H

Ring with alkene —> ether

Br₂/H₂O

Cleavage of ether

H-Br, H-Cl, H-I

Ring opening of epoxides with substitution

basic: RO-, amine, or lewis base

grignard reagent: 1. MgBrR, 2. H₃0X

Ring opening of epoxides trans 1-2 diols

acidic: H+,

Syn addition diol

KMnO₄ or OsO₄, H₂O₂

Anti addition diol

PBA, MCPBA, CH₃CO₃H

Diol to aldehydes, ketones

NaIO4, H₂O, or HIO4, THF, H₂O