Common Reagents used in Organic Synthesis

Oxidizing Agents

CrO3, H2SO4, H2O (= H2CrO4)
(H2CrO4in acetone = Jones Reagent)

Pyridinium Chlorochromate (PCC)
CrO3, Pyridine.HCl

Reducing Agents

NaBH4

LiAlH4(LAH)

Carbon Nucleophiles

Grignard Reagents
RMgX

example: CH3MgBr

Comments

Powerful Oxidizing Agent

1oOH to Carboxylic Acids
2o OH to Ketones

Mild and Selective Oxidizing Agent

1oOH to Aldehydes
2o OH to Ketones

Comments

Mild, Selective reducing agent

Carboxylic Acid - No Reaction
Ester - Slow (not Useful)
Ketone to 2oOH
Aldehyde to 1oOH

Powerful Reducing Agent

Carboxylic acid to 1oOH

reduces any carbonyl containing functional
groups to corresponding alcohol
α,βunsaturated ketones to 2o- OH leaves
double bond intact

Comments

Excellent Source of a Carbon Anion
Useful for forming C-C single bonds

Adds a methyl group

Can not use in the presence of acidic
hydrogens