Reagents

Using PBr3

Converts 1° and 2° alcohols → alkyl bromides

Using SOCl₂

Converts alcohols → alkyl chlorides

Dehydration with POCl₃

Converts alcohol → alkene

Uses POCl₃ + pyridine

NaBH₄

• Reduces:

  • Aldehydes → 1° alcohols

  • Ketones → 2° alcohols

• Does NOT reduce esters or acids

LiAlH₄ (LAH)

• Strong

• Reduces:

  • Aldehydes

  • Ketones

  • Esters

  • Carboxylic acids

Jones Reagent (CrO₃, H₂SO₄)

• 1° alcohol → carboxylic acid

• 2° alcohol → ketone

• Strong oxidizer

PCC

• 1° alcohol → aldehyde (stops here)

• 2° alcohol → ketone

Swern Oxidation

• 1° alcohol → aldehyde

• 2° alcohol → ketone

• Uses DMSO

Synthesis of Grignard Reagent

Alkyl halide + Mg → RMgX

grignard adds to carbonyl:

formaldehyde → 1° alcohol

aldehyde → 2° alcohol

ketone → 3° alcohol

ester (2 equivalents) → 3° alcohol

Aldehyde to carboxylic acid

H2CrO4