Organic Conditions and Reagents

All conditions and reagents of important organic reactions and/or mechanisms for AQA A-Level Chemistry

Thermal cracking

Overall: alkene → alkanes (+ H₂)

Conditions: 900^oC, 70 atm

Catalytic cracking

Overall: alkene → branched/cyclic alkanes, motor fuels

Conditions: 450^oC, 1-2 atm, zeolite catalyst

Nucleophilic substitution (using hydroxide ions)

Overall: halogenoalkane → alcohol

Reagents: NaOH or KOH

Conditions: warm, aqueous

Nucleophilic substitution (using ammonia)

Overall: halogenoalkane → amine

Reagents: excess NH3

Conditions: ethanolic, heat under pressure

Nucleophilic substitution (using cyanide ions)

Overall: halogenoalkane → nitrile

Reagents: KCN

Conditions: ethanolic, heat under reflux

Elimination (using hydroxide ions)

Overall: halogenoalkane → alkene

Reagents: NaOH or KOH

Conditions: ethanolic, heat under reflux

Electrophilic addition (using bromine)

Overall: alkene → dihalogenoalkane

Reagents: Br₂

Conditions: room temperature

Electrophilic addition (using hydrogen halides)

Overall: alkene → halogenoalkane

Reagents: HBr or HCl

Conditions: room temperature

Electrophilic addition (using sulfuric acid as a catalyst)

Stage 1:

Overall: alkene → alkylhydrogensulfate

Reagents: concentrated H₂SO₄

Conditions: room temperature

Stage 2:

Overall: alkylhydrogensulfate → alcohol

Reagents: water

Conditions: warm mixture

Electrophilic addition (acid-catalysed hydration of ethene)

Overall: ethene → ethanol

Reagents: steam, concentrated H₃PO₄ catalyst

Conditions: 300^oC, 70 atm

Partial oxidation (of primary alcohols)

Overall: primary alcohol → aldehyde

Reagents: limiting K₂Cr₂O₇ solution, dilute H₂SO₄

Conditions: gentle warming, distil immediately

Full oxidation (of primary alcohols)

Overall: primary alcohol → carboxylic acid

Reagents: excess K₂Cr₂O₇ solution, dilute H₂SO₄

Conditions: heat under reflux

Oxidation (of secondary alcohols)

Overall: secondary alcohol → ketone

Reagents: K₂Cr₂O₇ solution, dilute H₂SO₄

Conditions: heat under reflux

Acid-catalysed elimination (dehydration)

Overall: alcohol → alkene

Reagents: concentrated H₂SO₄ or H₃PO₄ catalyst

Conditions: warm, under reflux

Fermentation (of glucose)

Overall: glucose → ethanol + CO₂

Reagents: glucose, yeast

Conditions: 38^oC, in the absence of air

Nucleophilic addition (reduction of aldehydes)

Overall: aldehyde → primary alcohol

Reagents: NaBH₄ or LiAlH₄

Conditions: aqueous, ethanolic, room temperature and pressure

Nucleophilic addition (reduction of ketones)

Overall: ketone → secondary alcohol

Reagents: NaBH₄ or LiAlH₄, followed by dilute HCl

Conditions: aqueous, ethanolic, room temperature and pressure

Nucleophilic addition (using cyanide ions)

Overall: aldehyde or ketone → hydroxynitrile

Reagents: KCN and dilute H₂SO₄

Conditions: room temperature and pressure

Esterification (of carboxylic acids)

Overall: carboxylic acid + alcohol → ester + water

Reagents: carboxylic acid, alcohol, concentrated H₂SO₄ catalyst

Conditions: heat under reflux

Acid hydrolysis (of esters)

Overall: ester → alcohol + carboxylic acid

Reagents: dilute HCl

Conditions: heat under reflux

Base hydrolysis (of esters)

Overall: ester → alcohol + carboxylate salt

Reagents: excess dilute NaOH

Conditions: heat under reflux

Nucleophilic addition elimination (of acyl chlorides with water)

Overall: acyl chloride → carboxylic acid + HCl

Reagents: water

Conditions: room temperature

Observations: white misty fumes of HCl are given off

Nucleophilic addition elimination (of acid anhydrides with water)

Overall: acid anhydride → carboxylic acid (x2)

Reagents: water

Conditions: room temperature

Nucleophilic addition elimination (esterification of acyl chlorides)

Overall: acyl chloride → ester

Reagents: alcohol

Conditions: room temperature

Observations: white misty fumes of HCl are given off

Nucleophilic addition elimination (esterification of acid anhydrides)

Overall: acid anhydride → ester

Reagents: alcohol

Conditions: room temperature

Nucleophilic addition elimination (of acyl chlorides with ammonia)

Overall: acyl chloride → primary amide

Reagent: excess ammonia

Conditions: room temperature

Observations: white smoke of NH₄Cl is given off

Nucleophilic addition elimination (of acid anhydrides with ammonia)

Overall: acid anhydride → primary amide

Reagents: excess ammonia

Conditions: room temperature

Nucleophilic addition elimination (of acyl chlorides with primary amines)

Overall: acyl chloride → secondary amide

Reagents: excess primary amine

Conditions: room temperature

Nucleophilic addition elimination (of acid anhydrides with primary amines)

Overall: acid anhydride → secondary amide

Reagents: excess primary amine

Conditions: room temperature

Electrophilic substitution (nitration of benzene)

Overall: benzene → nitrobenzene

Reagents: concentrated HNO₃ in the presence of a concentrated H₂SO₄ catalyst

Electrophilic substitution (Friedel-Crafts acylation)

Overall: benzene → phenylketone

Reagents: acyl chloride in the presence of an anhydrous AlCl₃ catalyst

Conditions: 50^oC, heat under reflux

Reduction (of nitroarenes)

Overall: nitroarene → aromatic amine

Reagents: HCl, Sn catalyst

Conditions: heating

Reduction (of nitriles)

Overall: nitrile → primary amine

Reagents: LiAlH₄ in dry ether, followed by dilute HCl

Conditions: room temperature and pressure