Reaction + Reagents/Product [Alcohol, Oxidation, Reductions]

Alcohol Chemisitry (MAIN GOAL)

Turn OH into Good LG

• Trap Oxygen lone pair in Resonance {aka Pseudohalides}

• Protonate -OH for positive charge

• Use enthalpy/entropy to make it so that reaction can’t resist breaking the C-O bond

Pseudohalide Mechanism

Reagents: 1. Ms/Ts-X, Pyridine 2. (Nucleophile)- +(spec ion)

Product: OH replaced with Nucleophile

Dehydration

Reagents: H2SO4 (Strong Acid), heat

Product: OH removed and creates alkene (double bond)

Enthalpy (Sn2)

Reagents: PCl3 or PBr3

Product: Alcohol removed and replaced with Cl or Br in flipped orientation (ex: OH was dashed, Cl is Wedged)

Enthalpy (E2)

Reagents: POCl3 or POBr3, Pyridine (2 equivalent)

Product: OH and beta H removed to create double bond/alkene between beta carbon and alpha carbon

Entropy (Sn2)

Reagents: SOCl2, Pyridine

Product: OH replaced by Cl in flipped orientation + gaseous SO2Cl

Oxidation Synthesis

Carbon losing electrons/decreasing in oxidation number

• Primary OH —> Aldehyde

• Secondary OH —> Ketone

• Hydrate —> Carboxylic Acid

PCC

OXIDATION:

Reagent: PCC

Product: Ketone or Aldehyde (depending on if reactant was primary or secondary)

Dess Martin Synthesis

Reagent: DMP, CH2Cl2 (Aprotic Solvent)

Products: Ketone or Aldehyde (depending on if reactant was primary or secondary)

Jones Oxidation

Reagents: H2SO4, H2O2, H2O, Me2O (Acetone), CrO3

Product: Carboxylic Acid (from a PRIMARY ALCOHOL)

Reduction Synthesis

Cabron gaining electrons/Increasing Oxidation Number

“Reverse Oxidation” (Ketone —> Secondary OH; Aldehyde —> Primary OH)

Hydride

REDUCTION

Reagents: 1. NaBH4 or LiAlH4, MeOH (solv) 2. H3O+

Products: Ketone / Aldehyde become primary or secondary OH

Organometallic Reduction

Reagents: 1. Alkyne - + Na, gringard reagent (R-MgX) or Organolithium (R-Li; more reactive), THF (polar, aprotic solvent) 2. H3O+

Product: Tertiary or Secondary OH