Organic reactions, reagents and conditions

Alkane to halogenoalkane (+ mechanism name)

Cl2 or Br2; UV light (free radical substitution)

Alkene to halogenoalkane (+ mechanism name)

HX (gas); rtp (electrophilic addition)

halogenoalkane to alkene (+ mechanism name)

NaOH in ethanol; heat (elimination)

alkene to dihalogenoalkane (+ mechanism name)

Br2 or Cl2; rtp (electrophilic addition)

alcohol to halogenoalkane (+ mechanism name)

• HX (gas) at rtp

• KCl and conc. H2SO4 or H3PO4

• PCl3, heat

• PCl5 at rtp

• All nucleophilic substitution EXCEPT

• SOCl2 at rtp

halogenoalkane to alcohol (+ mechanism name)

NaOH (aq); heat OR AgNO3 (aq) in ethanol; warm (nucleophilic substitution)

Halogenoalkane to amine (+ mechanism name)

NH3 in ethanol; heated under pressure in a sealed tube (nucleophilic substitution)

halogenoalkane to nitrile (+ mechanism name)

KCN in ethanol; heat (nucleophilic substitution)

Alkene to polyalkene (+ mechanism name)

heat and high pressure

alkene to diol (+ mechanism name)

cold, dilute KMnO4 (oxidation)

Benzene to alkylbenzene

Chloroalkane and AlCl3 catalyst, heat

Acylation of benzene

acyl chloride and AlCl3 catalyst, heat

Halogenation of benzene

Cl and AlCl3 cat (or Br and AlBr3 cat)

nitration of benzene

Conc H2SO4, conc HNO3, 25-60*C

benzene to cyclohexane

Hydrogen gas with a Pt or Ni catalyst

benzene with a side chain to benzoic acid

Hot, alkaline KMnO4. THEN HCl (aq)

Carboxylic acid to acyl chloride

SOCl2 / PCl5 / PCl3 and heat

nitrobenzene to phenylamine

Sn and conc HCl and heat, THEN NaOH (aq)

Multiple bromination of phenylamine

Br2 (aq), rtp

phenylamine to diazonium salt

NaNO2 and HCl (aq), temp below 10*C

diazonium salt to azo dye

phenol and NaOH

diazonium salt to phenol

H20, warm

multiple brominnation of phenol

Br2 (aq), rtp

Phenol to phenoxide

NaOH (aq)

nitration of phenol

HNO3 (aq), rtp

Primary alcohol to carboxylic acid

acidified potassium dichromate, heat under reflux

primary alcohol to aldehyde

acidified potassium dichromate, heat with distillation

carboxylic acid to alcohol

lithium aluminium hydride in dry ether

Acyl chloride to ester

alcohol

ester to carboxylic acid and alcohol

H2SO4, heat, hydrolysis

nitrile to carboxylic acid

aqueous HCl and heat or aqueous NaOH and heat

carboxylic acid to carboxylate ion

NaOH (neutralisation)

Alkene to carboxylic acid

hot, acidified KMnO4 - works with alkenes that have an R group and a H on each carbon forming the double bond

ethanedioic acid to CO2

H2SO4 or KMnO4

methanoic acid to carbon dioxide

tollen’s / fehling’s / KMnO4 / K2Cr2O7

Difference between ester hydrolysis with aqueous acid and aqueous alkali

Acid - forms carboxylic acid. Alkali - forms carboxylate salt

acyl chloride to amide

amine

Phenoxide to benzene-ester (?)

acyl chloride