Organic 2 Chapter 19 Reactions

PCC or DMP, CH₂Cl₂

or 1) DMSO, (COCl)₂

2) Et₃N

Oxidation of an alcohol to a primary aldehyde

1) O₃

2) DMS

Ozonolysis of an alkene to an aldehyde

1) R₂BH

2) H₂O₂, NaOH

Hydroboration-Oxidation of a terminal Alkyne to an aldehyde.

Na₂Cr₂O₇

H₂SO₄, H₂O

Chromic Acid Oxidization

H₂SO₄, H₂O

HgSO₄

Acid-Catalyzed Hydration of terminal alkynes

Acyl Chloride

AlCl₃

Friedel-Crafts Acylation

1) RMgBr

2) H₂O

Grignard Reaction

H₂O

NaOH/H₂SO₄

Forms a diol at the carbonyl

2ROH

TsOH/H₂SO₄

-H₂O

Formation of an Acetal

H₂SO₄

RNH₂

-H₂O

Imine formation

H₂SO₄

R₂NH

-H₂O

Enamine formation

H₂SO₄

2RSH

-H₂O

Thioacetal formation

1) LAH

2) H₃O⁺

or

NaBH₄, MeOH

Reduction of a ketone to a secondary alcohol

HCN

Cyanohydrin Formation

Cyanohydrin + 1) LAH

2) H₂O

Results in a primary amine

Cyanohydrin + H₃O⁺

Results in a carboxylic acid

Ph₃PCH₂

Witting Reaction

1) XR, PPh₃

2) BuLi

Wittig Reagent Formation

RCO₃H

Baeyer-Villiger Oxidation

H > 3* > 2* or Ph > 1* > Me

Baeyer-Villiger Oxidation Migration rate