Organic Reactions Edexcel A-level Chemistry

Alkane to Halogenoalkane

free radical substitution, halogen, UV light

Alkene to Alkane

reduction/addition, hydrogen gas, Nickel catalyst and 150°C

Alkene to Dihaloalkane

electrophilic addition, halogen, room temperature

Dihaloalkane to diol

nucleophilic substitution, KOH aqueous, heat under reflux,

Alkene to Alcohol

electrophilic addition, steam, catalyst conc H3PO4, 300°C and 60-70 atm

Alkenes to diol

oxidation, shake in H+/Potassium manganate solution, purple to colourless solution

Alkene to Halogenoalkane

electrophilic addition, hydrogen halide and room temp

Halogenoalkane to Alcohol

Nucleophilic substitution, reflux with warm aqueous KOH

Halogenoalkane to Nitrile

nucleophilic substitution, reflux with potassium cyanide in ethanol

Halogenoalkane to Primary amine

Nucleophilic substitution, warm with excess ethanolic ammonia in a sealed tube

Halogenoalkane to Alkene

elimination, reflux with KOH in ethanol

Alcohol to Chloroalkane

nucleophilic substitution, PCl5 and 20°C for primary and secondary, concentrated HCl if tertiary.

Alcohol to Bromoalkane

nucleophilic substitution, KBr, conc H2SO4 and 20°C

Alcohol to Iodoalkane

nucleophilic substitution, red phosphorus and iodine

Alcohol to Alkene

elimination, concentrated H3PO4

Primary alcohol to Aldehyde

oxidation, K2Cr2O7, H2SO4, heat and distil off

Primary alcohol to carboxylic acid

oxidation, excess K2Cr2O7, H2SO4 and heat under reflux

Secondary alcohol to Ketone

oxidation, excess K2Cr2O7, H2SO4 and heat under reflux

Aldehyde to Primary alcohol

reduction, LiAlH4 in dry ether

Ketone to Secondary alcohol

reduction, LiAlH4 in dry ether

aldehyde/ketone to hydroxy nitrile

nucleophilic addition, HCN or KCN

Nitrile to Carboxylic acid (acidic conditions)

Reflux with dilute HCl and then distil carboxylic acid

Carboxylic acid to Primary alcohol

reduction, LiAlH4 in dry ether

Carboxylic acid to Acyl chloride

nucleophilic acyl substitution, PCl5

Carboxylic acid to Ester

esterification, reflux with concentrated H2SO4 and alcohol, heat

Alcohol to ester

esterification, carboxylic acid and H2SO4, heat

Ester to Alcohol and Carboxylate ion

Reflux with dilute alkali (NaOH)

Acyl chloride to Ester

nucleophilic addition elimination, alcohol, room temperature

Acyl chloride to primary Amide

addition elimination, NH3, room temperature

Acyl chloride to secondary amide

addition elimination, primary amine, room temperature

Acyl chloride to carboxylic acid

addition elimination, H2O, room temp

Arene to bromoarene

electrophilic substitution, Br2, FeBr3 and room temperature

Arene to chloroarene

electrophilic substitution, Cl2, FeCl3, room temperature

Arene to Alkyl benzene

electrophilic substitution, reflux with chloroalkane and AlCl3 (Friedel-Crafts)

Arene to Phenylketone

electrophilic substitution, reflux with acyl chloride and AlCl3

Arene to Nitroarene

electrophilic substitution, warm with concentrated HNO3 and H2SO4

Phenol to 2,4,6-Tribromophenol

electrophilic substitution, shake with bromine water at room temperature to give white ppt

Aspirin formation

Salicylic acid and ethanoic anhydride with a few drops of phosphoric acid. Warm to 50°C, then add cold water and cool on ice. Filter the crystals then recrystallize the aspirin

Primary amine to secondary/tertiary amine

nucleophilic substitution, haloalkane, heat

Halogenoalkane to amine

nucleophilic substitution, excess concentrated ammonia in ethanol and heat in a sealed tube

Nitrile to Primary amine

reduction, warm with LiAlH4 in dry ether followed by dilute acid

Amide to primary amine

reduction, warm with LiAlH4 in dry ether followed by dilute acid

Nitrobenzene to phenyl amine

reduction, reflux with tin and concentrated HCl then add excess sodium hydroxide

Amine to secondary amide

nucleophilic addition elimination, acyl chloride, room temperature

acyl chloride to primary amide

addition elimination, ammonia in ethanol

acyl chloride to secondary/tertiary amide

reaction continues HCl reacts with the amide to form a salt

Amide to carboxylic acid (acidic conditions)

hydrolysis, H+ and H20

Amide to carboxylic acid (alkali conditions)

hydrolysis, OH-, produces carboxylate salt

Amine with water

acid base, react reversibly to form alkylammonium ions and hydroxide ions

Amine with acid

neutralisation, forms alkylammonium salt

Amine with transition metal ions

Forms a ligand

Amine with acyl chloride

addition elimination, secondary amide

Amine with haloalkane

nucleophilic substitution, salt of secondary alkylammonium ions (tertiary if excess haloalkane)

Dicarboxylic acid and diol

condensation polymerisation, polyester, H2O

Diacyl chloride and diol

condensation polymerisation, polyester, HCl

Polyester to carboxylic acid (acidic conditions)

hydrolysis, reforms both monomers

Polyester to carboxylic acid (alkali conditions)

hydrolysis, diol reformed, salt of dicarboxylic acid formed

diacyl chloride and diamines

condensation polymerisation, polyamides, HCl

dicarboxylic acid and diamides

condensation polymerisation, polyamides, H2O