Edexcel A Level (a2) Chemistry Organic Chemistry 5s6n72

Reaction of…

Reaction with…

Organic product

Mechanism/

Carbonyl compounds

Hydrogen cyanide, HCN 2,4-DNPH

Cyanohydrin (Hydroxynitriles) Derivative (hydrazone)

Nucleophilic addition Condensation

Conditions

Type of reaction

(Addition-elimination)

Aldehyde

Aldehyde

LiAlH4 (dry ether)

Primary alcohol

OR, Ketone

NaBH4 (water/ dry ether /ethanol) K2Cr2O7 /H+ I2 / NaOH

Reduction Secondary alcohol

Carboxylic acid Iodoform; Sodium carboxylate Carboxylic acid

Oxidation Iodoform reaction

Heat under reflux Warm if necessary

Hydrolysis

Catalyst -H2SO4

Nitrile

Water

Cyanohydrin

Water

Hydroxycarboxylic acid

PCl5

Acyl chloride

Halogenation

LiAlH4 Na2CO3 / NaHCO3 / NaOH Alcohol (Reversible)

Primary alcohol Salt, CO2, H2O

Reduction Neutralisation

Dry ether

Ester

Esterification/ Condensation

Strong acid; Warm; Add Na2CO3

Water

Carboxylic acid

Alcohol

Ester

SN

Ammonia (conc.)

1° amide

SN

Primary amines

2° amide

SN

[Dilute acid (strong)]

Carboxylic acid

Acyl chlorides

Nitrating mixture (Nitric acid)

Nitrobenzene (& water)

Nitration; SE

H2SO4; hur; Temp-55oC

Chloroalkane

Alkyl benzene

FC Alkylation; SE

Catalystanhydrous AlCl3

Acyl chloride

Phenyl ketone

FC Acylation; SE

Catalystanhydrous AlCl3

Bromine

Bromobenzene

Bromination; SE

Catalystanhydrous AlBr3/FeBr3

Oxidation of side chain

Benzaldehyde; Benzoic acid

Oxidation

Acidified/Alkaline

Oxygen

CO2, H2O

Combustion

Fuming sulfuric acid

Benzenesulfonic acid

Sulfonation

Hydrogen

Cyclohexane

Free radical addition

Catalyst - Raney nickel; 60oC

Bromine

1,2,3,4,5,6hexabromocyclo hexane

Free radical addition

UV radiation

NaOH soln

Sodium phenate (& water)

Ethanoyl chloride

Phenyl ethanoate (& HCl)

Bromine

2,4,6tribromophenol

Benzene

Phenol (WHITE PPT) (& HBr)

Nitric acid (dil.)

2,4,6-trinitrophenol (WHITE PPT) (& water)

KMnO4 soln; warm

Amine (Prep.) Halogenoalkanes

Ammonia

1°, 2°, 3° amines & 4° ammonium salts

Nitriles

Alkyl amine (1o)

Reduction

Amides

Alkyl amine (1o)

Reduction

Primary amines

Aqueous hydrogen ions

Alkyl/Phenyl ammonium ions

Aqueous copper (ii) ions

Tetraaminediaqua copper (ii) ion (& water)

Acyl chloride

2o amide

Nitrobenzene

Phenyl amine

Reduction

Ethanol solvent; Sealed; Heat Reducing agent-LiAlH4; Solvent-- Dry ether Hydrolysis with dil. HCl Distil with NaOH Reducing agent-LiAlH4; Solvent-- Dry ether Hydrolysis with dil. HCl Distil with NaOH

Tin and conc. HCl

Phenyl amine

Nitrous acid

Benzenediazonium ion

Temp0 oC -10 oC NaNO2 & HCl

Benzene diazonium ion

Phenol

Azo-dye

dil. NaOH soln