AQA A-Level Organic Synthesis

Alkane to Halogenoalkane

X2, UV light
Mechanism = free radical substitution

Halogenoalkane to Alkene

KOH, dissolved in ethanol and heated under reflux
Mechanism = Elimination

Alkene to Halogenoalkane

HX at room temperature
Mechanism = Electropholic Addition

Halogenoalkane to Alcohol

Warm NaOH/KOH, heated under reflux
Mechanism = Nucleophilic Substitution

Halogenoalkane to Nitrile

KCN, dissolved in ethanol and heated under reflux
Mechanism = Nucleophilic Substitution

Halogenoalkane to Primary Amine

Use a primary Halogenoalkane, excess ammonia and heat
Mechanism = Nucleophilic Substitutuon

Halogenoalkane to Secondary/Tertiary Amines, their Salts and Quaternary Ammonium Salts

Use a non primary Halogenoalkane and excess ammonia and heat
Mechanism = Nucleophilic Substitution

Nitrile to Primary Amine

LiAlH4 with a dilute acid
OR
H2 gas with a nickel catalyst at a high temperature
Reaction type = Reduction

Alkene to Dibromoalkane

This is the test for an Alkene.
Add bromine water at room temperature
Solution will decolourise if Alkene is present.

Alkene to Alcohol

H3PO4 catalyst, steam at 300 deg at 60 atm
Reaction type = Hydration
OR
H2O with a cold H2SO4 catalyst
Mechanism = electrophilic Addition

Alcohol to Alkene

Concentrated H2SO4 heated under reflux
Mechanism = Elimination

Alcohol to Aldehyde

Primary Alcohol, acidified potassium dichromate and heated under distillation
Reaction type = Oxidation

Alcohol to Ketone

Secondary Alcohol, acidified potassium dichromate and heated under reflux
Reaction type =
Oxidation

Aldehyde/Ketone to Alcohol

NaBH4, in Water with Methanol
Mechanism = Nucleophilic Addition

Aldehyde to Carboxylic Acid

Acidified potassium dichromate heated under reflux
Reaction type = Oxidation

Aldehyde/Ketone to Hydroxynitrile

KCN, H2SO4 at room temperature
Mechanism = nucleophilic Addition

Alcohol to Carboxylic Acid

Primary alcohol acidified potassium dichromate heated under reflux
Reaction type = Oxidation

Ester to Carboxylic Acid

Dilute H2SO4 catalyst, H2O, heated under reflux
Reaction type = Acid Hydrolysis
OR
Dilute NaOH, heated under reflux
Reaction type = Base Hydrolysis

Carboxylic Acid to Ester

Alcohol, concentrated H2SO4 catalyst and heat
Reaction type =
Esterification

Acyl Chloride / Acid Anhydride to Carboxylic Acid

H20 at room temperature
Mechanism = Nucleophilic Addition Elimination

Acyl Chloride / Acid Anhydride to Ester

Alcohol at room temperature Mechanism = Nucleophilic Addition Elimination

Acyl Chloride / Acid Anhydride to Primary Amine

NH3 at room temperature
Mechanism = Nucleophilic Addition Elimination

Acyl Chloride / Acid Anhydride to N-substituted Amide

Amine at room temperature
Mechanism = Nuclephilic Addition Elimination

Benzene to Nitrobenzene

Concentrated H2SO4, Concentrated HNO3 (to make the NO2+) below 50 deg
Mechanism = Electrophilic Substitution (when attaching to benzene)

Benzene to Phenylketone

RCOCL, ALCL3 catalyst, heated under reflux and in a non-aqueous environment
Reaction type = Friedel-Crafts Acylation

Nitrobenzene to Aromatic Amine

Tin, Concentrated HCl, heated under reflux then add NaOH
Reaction type = Reduction

Aromatic Amine to N-Phenylethanamide

CH3COCl, r.t.p

The test to distinguish between aldehyde and ketones

Tollen's reagent. If aldehyde is present then a silver mirror will form on the test tube (silver precipitate)