Orgo 2 mechanisms I forget, etc.

Amide → Nitrile

POCl₃

Permanganate oxidation

1) KMnO₄, H₂O, 100^°C

alkene → carboxylic acid +/ ketone

conc. KMnO₄

Phosphorus Ylide formation

1) PPh₃ + CH₂RBr

2) BuLi

Ketone → Alkene

(Wittig Reaction)

PPh₃CRH

Alkyne → Aldehyde (Hydration-Boration)

1) Sia₂BH

2) H₂O₂, ^-OH

anti-markovnikov hydration, tautomerism enol → keto

Friedels-Craft: HF

alkene + HF → carbocation

alcohol + BF₃/HF → Carbocation

• → carbocation reaction with phenol

aldehyde/ketone → alkane

(Wolff-Kishner)

1) NH₂NH₂, H⁺

2) KOH, Δ, DMSO

R (vinyl/aryl) + R’ → R—R’ (preserved stereochem)

(Suzuki Reaction)

R—X + R’—B(OH)₂

• boronate ester/acid made by:

  • R—= + H—B(OH)₂

R (vinyl/aryl) + R’ → R—R’ (trans)

(Heck reaction)

• R—X + =—R’

• with Pd/Et₃N

Reduction of Diazonium → Benzene

H₃PO₂

alkene → carboxylic acids

1) O₃

2) H₂O₂

alkyne → carboxylic acids

1) O₃

2 H₂O

OR

Hot, conc. KMnO₄

Primary Amine Formation: Azide

1) R—X, NaN₃

2) LiAlH₄

3) H₂O

OR

2) H₂/Pd

Primary Amine Formation: Gabriel Synthesis

1) Phthalimide anion + R—X

2) NH₂NH₂, Δ

R—OH → R—Br

PBr₃

R—Br → alkene

NaOCH₃ or NaOH

Elimination

aldehyde → alcohol

• NaBH₄

• NiH₂

• H₂/Pd

• DIBAL-H

Carboxylic acid (only) → alcohol

BH₃·THF/H₃O⁺

aldehyde (only) → carboxylic acid

Tollen’s:

Ag⁺/NH₃/H₂O

alcohol → Carboxylic acid

• excess NaOCl, TEMPO

• Na₂Cr₂O₇/H₂SO₄

• hot, conc. KMnO₄, H₂O

syn dihydroxylation

• cold, dilute KMnO₄, ^-OH, H₂O

• OsO₄, H₂O₂

alcohol→ alkane

1) TsCl/pyridine

2) LiAlH4

3° alcohol → R—X

H-X (SN1)

1°/2° alcohol → R—X

R—Cl: SOCl₂

R—Br: PBr₃

R—I: P + I₂