lec 5 reactions

Primary oxidation: CH₃CH₂OH ──[O]──▶

CH₃CHO ──[O]──▶ CH₃COOH 🔥⬆️⬆️

Secondary oxidation: CH₃CH(OH)CH₃ ──K₂Cr₂O₇/H⁺⚡──▶

CH₃COCH₃ ⚖️⬆️

Tertiary oxidation: (CH₃)₃COH ──[O]──▶

∅ 🚫

Dehydration (ether): 2 C₂H₅OH ──H₂SO₄🧪🔥(140)──▶

C₂H₅–O–C₂H₅ + H₂O 🔗💧

Dehydration (alkene): C₂H₅OH ──H₂SO₄🧪🔥🔥(180)──▶

CH₂=CH₂ + H₂O 💨💧

Esterification: CH₃COOH + C₂H₅OH ⇌H⁺⚡⇌

CH₃COOC₂H₅ + H₂O 🍍💧

General ester: Ar/R–OH + R'–COOH ⇌H⁺⚡⇌

Ar/R–OCOR' + H₂O 🔄💧

Aspirin: Salicylic + (CH₃CO)₂O ──H⁺⚡──▶

Aspirin + CH₃COOH 💊

Alcohol + Na: 2 ROH + 2 Na ──▶

2 RONa + H₂⬆️ ⚡

Ether prep: 2 R–OH ──H₂SO₄🧪🔥(130–140)──▶

R–O–R + H₂O 🔗💧

Ether cleavage (aliphatic): R–O–R' + HI/HBr⚡ ──▶

R–OH + R'–X ✂️

Ether cleavage (aromatic): Ar–O–R + HX⚡ ──▶

Ar–OH + R–X 🧠

Anisole bromination: Ar–OCH₃ + Br₂ ──CH₃COOH⚡──▶

p + o 🎯

Anisole nitration: Ar–OCH₃ + HNO₃/H₂SO₄🧪⚡ ──▶

p + o 💥

Friedel alkylation: Ar–OCH₃ + CH₃Cl ──AlCl₃⚡/CS₂──▶

p + o 🧲

Friedel acylation: Ar–OCH₃ + CH₃COCl ──AlCl₃⚡──▶

p + o 🧪

Dow process: C₆H₅Cl + NaOH💧 ──🔥🔥(623K)

300atm──▶

Sulfonic route: C₆H₆ ──Oleum🧪──▶ C₆H₅SO₃H ──NaOH💧/H⁺⚡──▶

C₆H₅OH 🔄

Phenol + Na: 2 C₆H₅OH + 2 Na ──▶

2 C₆H₅ONa + H₂⬆️ ⚡

Phenol + NaOH: C₆H₅OH + NaOH💧 ──▶

C₆H₅ONa + H₂O 💧

Phenol nitration (dil): C₆H₅OH + HNO₃💧 ──▶

o + p 🎯

Phenol nitration (conc): C₆H₅OH + HNO₃🧪 ──▶

2

Phenol bromination (273K): C₆H₅OH + Br₂ ──CS₂⚡❄️(273K)──▶

p + o 🧭

Phenol bromination (excess aq): C₆H₅OH + 3Br₂💧 ──▶

2

Zn reduction: C₆H₅OH + Zn ──▶

C₆H₆ + ZnO 🧹

Phenol oxidation: C₆H₅OH + Na₂Cr₂O₇/H₂SO₄🧪⚡ ──▶

C₆H₄O₂ ⚙