Alcohol Reactions - Organic Chemistry I Midterm 4

1º Alcohol + HX

Produces Haloalkane (R—X + H₂O)

1º and 2º Alcohols + PBr₃

Removes -OH group and replaces it with Br (inverts stereochemistry)

1º and 2º Alcohols + SOCl₂ (or SOBr₂), Et₃N (or pyridine)

Replaces -OH group with Cl (if used SOCl₂) or Br (if used SOBr₂); inverts stereochemistry

1º and 2º Alcohols + TsCl (or MsCl), Et₃N (or pyridine)

Produces a Sulfonate (-OTs)

Acid-Catalyzed Dehydration

3º and 2º Alcohols + H₂SO₄, heat

Removes -OH group and adds double bond (Zaitsev)

Acid-Catalyzed Dehydration

1º Alcohols (not common) + H₂SO₄, heat

Produces an alkene; Major product (zaitsev) and minor product (non-Zaitsev)

Oxidation of Alcohols (Jones Reagent)

1º alcohol —> carboxylic acid

2º alcohol —> ketone

3º alcohol —> no rxn

Oxidation of Alcohols (PCC)

1º alcohol —> aldehyde

2º alcohol —> ketone

3º alcohol —> no rxn

Oxidation of Alcohols (Periodic Acid:HIO₄)

Glycol (2 carbonyl groups); Splits between cis -OH groups