OCR A LEVEL CHEMISTRY SYNTHETIC ROUTES

Alkane → Halo alkane

Halogen, UV light, Radical substitution

Halo alkane → Nitrile

KCN in ethanol, Nucleophilic substitution

Halo alkane → Amine

NH3 in ethanol, heat , Nucleophilic substitution

Haloalkane → Alcohol

NaOH (aq) > heat > Nucleophilic substitution

Alkene → Haloalkane

Hydrogen halide (eg. HBr) > electrophilic addition

Alkene → Alkane

H2 Ni catalyst, 150°C > Hydrogenation

Alkene → Alcohol

steam / H3PO4 / high temperature / high pressure (electrophilic addition) .

Alcohol → Haloalkane

Nax + H2SO4 , substitution

Alcohol → Alkene

conc H2SO4 or H3PO4 > heat .

Primary Alcohol → Aldehyde

K2Cr2O7/H2SO4 / heat/ distillation

primary alcohol → carboxylic acid

Acidified potassium dichromate/ heat/ reflux

secondary alcohol → ketone

Acidified potassium dichromate/ heat/ reflux

Alcohol → ester

carboxylic acid or acid anhydride + conc sulfuric acid

Aldehyde → Hydroxynitrile

NaCN (aq), H+ (aq)

ketone → Hydroxynitrile

NaCN(aq)/H+(aq)

Aldehyde → Carboxylic acid

K2Cr2O7, H2SO4, reflux

ketone → secondary alcohol

NaBH4

Aldehyde → primary alcohol

NaBH4

Nitrile → carboxylic acid

hydrochloric acid or water + heat

Nitrile → amine

H2/Ni

hydroxynitrile → carboxylic

acid

Dilute HCL + heat

Ester → carboxylate salt

NaOH + heat

carboxylic acid → acyl chloride

SOCl2

Acyl chloride → Ester

Alcohol

Acyl chloride → carboxylic acid

H2O

Acyl chloride → primary amide

NH3

Acyl Chloride → secondary amide

primary amine

Benzene → Nitrobenzene

conc nitric acid + conc sulfuric

acid

Nitrobenzene → phenylamine

Sn + conc HCL

Benzene → 2,4,6 tri-bromophenylamine

Br 2

Benzene → Bromo benzene

Br2 + ALBr3 or FeBr3

Benzene → chlorobenzene

Cl2, FeCl3 or AlCl3

Benzene → Methyl benzene

CH3Cl + AlCl3

Benzene → Phenyl ketone

CH3COCl + AlCl3

Phenyl ethanone → hydroxy compound

Na BH4

Phenol → 2,4,6 tri-bromophenol

Br2

Phenol → sodium Phenoxide

NaOH(aq)

Phenol → 2 nitrophenol + 4 nitrophenol

Dilute HNO3