CHEM241 Exam 2 Reagents

Reagents for (1) Ketones and Aldehydes, (2) Carboxylic Acids, and (3) Carboxylic Acid Derivatives

Mild oxidizing reagents to prepare aldehydes and ketones

PCC or Dess-Martin; solvent: CH₂Cl₂

Note: For primary alcohols

Strong oxidizing reagents to prepare aldehydes and ketones

Jones Reagent – H₂CrO₄; solvent: H₂O, acetone

Note: Not for primary alcohols; they will become carboxylic acids due to reagent strength

Oxidizing reagents for adjacent diols

HIO₄ (periodic acid)

Note: For 1,2-diols

Reagents for ozonolysis and mild reduction of alkenes

1) O₃

2) (CH₃)₂S

Note: Order of steps matters

Reagents for hydroboration and oxidation

1) (sia)₂BH

2) H₂O₂, NaOH

Note: Order of steps matters

Reagents for oxymercuration and hydrolysis

H₂SO₄; solute: HgSO₄

Reagents for pinacol rearrangement

H₂SO₄ (catalyst); heat

Reagents when Grignard reagent is the nucleophile

Mg, solvent: ether or THF

Note: No water

Reagents when organolithium is the nucleophile

HCl; solvent: H₂O

Note: More active and difficult to handle than Grignard

Reagents when terminal alkyne anion is the nucleophile

Reagents when cyanide is the nucleophile