Edexcel A level (A2) Chemistry Organic Chemistry

Reaction o f  Carbonyl compounds …

Reaction with  Hydrogen cyanide, HCN 2,4-DNPH …

Aldehyde

Aldehyde

LiAlH 4 (dry ether )

Organic product Cyanohydrin (Hydroxynitriles) Derivative (hydrazone)

Nitrile

NaBH4 (water/ dry ether /ethanol) K2Cr 2O7 /H+ I2 / NaOH Water

Conditions

Type of reaction 

Nucleophilic addition Condensation (Addition-elimination)

Primary alcohol

OR, Ketone

Mechanism/

Reduction Secondary alcohol

Carboxylic acid Iodoform; Sodium carboxylate Carboxylic acid

Oxidation Iodoform reaction

Heat under reflux Warm if necessary

Hydrolysis Hydrolysis

Catalyst   - --

H2SO4 [Dilute acid (strong)]

Cyanohydrin

Carboxylic acid

Water

Hydroxycarboxylic acid

PCl5

Acyl chloride

Halogenation

Primary alcohol Salt, CO2, H2O

Reduction Neutralisation

Dry ether

Ester

Esterification/ Condensation

Strong acid; Warm;  Add Na2CO3

LiAlH 4 Na2CO3 / NaHCO3 / NaOH  Alcohol (Reversible)

Water

Carboxylic acid

 Alcohol

Ester

SN

 Ammonia (conc.)

1  amide  amide

SN

Primary amines

2  amide  amide

SN

Acyl chlorides °

°

Nitrating mixture (Nitric acid)

Nitrobenzene (& water)

Nitration; SE

H2SO4; hur; Temp-55oC

Chloroalkane

Alkyl benzene

FC Alkylation; S E

Catalyst  -

anhydrous AlCl 3  Acyl chloride

Phenyl ketone

FC Acylation; S E

Catalyst  -

anhydrous AlCl 3

Benzene

Catalyst  -

Phenol

Bromine

Bromobenzene

Bromination; S E

anhydrous  AlBr 3/FeBr 3

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

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 (WHITE PPT) (& HBr)

Nitric acid (dil.)

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

KMnO4 soln; warm

nickel; 60oC

Amine (Prep.) 1 , 2 , 3  amines & 4 ammonium salts °

Halogenoalkanes

 Ammonia

°

°

°

Nitriles

 Alkyl amine (1 o)

Reduction

Amides

 Alkyl amine (1 o)

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-LiAlH 4; Solvent-- Dry ether Hydrolysis with dil. HCl Distil with NaOH Reducing agent-LiAlH 4; 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