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Formation of epoxide

MCPBA, attacks more electron-filled double bond

Acid-catalyzed opening of epoxides in water

Acid (H⁺), Water (H₂O) (adds two OH groups on carbons)

Acid-catalyzed opening of epoxides in alcohols

Acid (H⁺), Alcohol (R—OH) (alkoxy group attacks more substituted side)

Acid-catalyzed opening of epoxides in alcohols

Acid (H⁺), Alcohol (R—OH) (alkoxy group attacks more substituted side)

Base-catalyzed opening of epoxides with alkoxides or hydroxide

Alkoxy group bonds to less substituted side

Electrophilic aromatic substitution

Halogenation:Br₂, FeBr₃ (for bromination)

Electrophilic aromatic substitution

Nitration:HNO₃, H₂SO₄ (NO2 added)

Friedel-Crafts Alkylation (adding alkyl group to benzene ring)

Alkyl chloride (R—Cl), AlCl₃

Friedel-Crafts Alkylation (adding alkyl group to benzene ring)

Alkyl chloride (R—Cl), AlCl₃

Protonation of Alkenes

HF will form cation, will attack aromatic ring

Clemmenson reaction

Acyl chloride+ AlCl3, then add ZnHg to take off the carbonyl to make it a long alkane group

Nucleophilic Aromatic Substitution

F>Cl>Br>I, Add nucleophile

Suzuki reaction adding alkene/aromatic/alkyl to aromatic ring

Aryl halide, boronic acid (R-B-(OH)2, Pd catalyst

Addition of chlorine to benzene

Reagent:Chlorine gas (Cl₂), Conditions:Heat and pressure or light

Grignard reaction with epoxides

Grignard reagent (RMgX), epoxide

Addition of chlorine to benzene

Reagent:Chlorine gas (Cl₂), Conditions:Heat and pressure or light

Oxidation of an alkyl side chain on benzene to a carboxylic acid

Reagent:Potassium permanganate (KMnO₄, hot and concentrated)

Halogenation of an alkyl side chain on benzene

Reagent:Bromine (Br₂) with light (hv)

Synthesizes ethers from alcohols and halides

Reagents:Alkoxide ion (R—O⁻) and primary alkyl halide (R'—X) (Williamson Ether Synthesis)

Nucleophilic substitution at a benzylic position

Reagent:Nucleophile (Nuc⁻), Conditions:Activated benzylic position

Oxidation of phenols to quinones

Reagents:Sodium dichromate (Na₂Cr₂O₇) in sulfuric acid (H₂SO₄)

Synthesizes ethers from alcohols and halides

Reagents:Alkoxide ion (R—O⁻) and primary alkyl halide (R'—X) (Williamson Ether Synthesis)

Synthesizes ethers via alkene addition

Reagents:Alkene, Mercury(II) acetate (Hg(OAc)₂), alcohol followed by reduction with Sodium borohydride (NaBH₄) (Alkoxymercuration-Demercuration)

The heck reaction; adding alkene to aromatic ring

Ar-X+ alkene-X+ Pd(OAc)2/Pph3, et3n= Ar-alkene-X