Organic Synthesis

What are the reagents and conditions to convert an alkene to a halogenoalkane?

HBr (or HCl/ HI ) hydrogen halide at room temperature

What type of reaction converts an alkene to a halogenoalkane?

Electrophilic addition

What are the reagents and conditions to convert an alkene to a dihalogenoalkane?

Br₂ (or Cl₂) at room temperature

What are the reagents and conditions to convert an alkene to an alcohol?

Steam (H₂O(g)) with H₃PO₄ catalyst at high temperature 300 degrees and pressure 60 atm

What is this reaction to go from alkene to alcohol called?

Hydration (addition)

What are the reagents and conditions to convert an alkene to an alkane?

H₂ with Ni catalyst at approximately 150°C

What is the reaction to go from alkene to alkane called? →

Hydrogenation (addition)

What are the reagents and conditions to convert a halogenoalkane to an alcohol?

NaOH (aqueous) with warming under reflux

What type of reaction converts a halogenoalkane to an alcohol?

Nucleophilic substitution

What are the reagents and conditions to convert a halogenoalkane to a nitrile?

KCN in aqueous ethanol under reflux

What type of reaction converts a halogenoalkane to a nitrile?

Nucleophilic substitution

What are the reagents and conditions to convert a halogenoalkane to a primary amine?

Excess NH₃ in ethanol with heat in a sealed container

What type of reaction converts a halogenoalkane to a primary amine?

Nucleophilic substitution

What are the reagents and conditions to convert a halogenoalkane to an alkene?

NaOH in ethanol (anhydrous) with heat under reflux

What type of reaction converts a halogenoalkane to an alkene?

Elimination

What are the reagents and conditions to convert an alcohol to an alkene? What type of reaction is it?

Concentrated H₂SO₄ or concentrated H₃PO₄ with warming at approximately 170°C. Elimination (dehydration)

What are the reagents and conditions to convert a primary alcohol to an aldehyde?

K₂Cr₂O₇ / H₂SO₄ with warming and distillation

What type of reaction converts a primary alcohol to an aldehyde?

Oxidation

What are the reagents and conditions to convert a primary alcohol to a carboxylic acid?

Excess K₂Cr₂O₇ / H₂SO₄ under reflux

What are the reagents and conditions to convert a secondary alcohol to a ketone?

K₂Cr₂O₇ / H₂SO₄ under reflux

What are the reagents and conditions to convert an alcohol to an ester?

Carboxylic acid with concentrated H₂SO₄ catalyst under warming and reflux

What type of reaction converts an alcohol to an ester?

Esterification (condensation)

What are the reagents and conditions to convert an aldehyde or ketone to an alcohol?

NaBH₄ in water or methanol

What type of reaction is the reduction from a carbonyl ketone/ aldehyde to an alcohol?

Nucleophilic addition, the hydride acts as a nuclephile

What are the reagents and conditions to convert an aldehyde or ketone to a hydroxynitrile?

KCN followed by H₂SO₄ (or HCN/KCN)

What type of reaction converts a carbonyl to a hydroxynitrile?

Nucleophilic addition

What are the reagents and conditions to convert an aldehyde to a carboxylic acid?

K₂Cr₂O₇ / H₂SO₄ under reflux

What are the reagents and conditions to convert a carboxylic acid to an ester?

Alcohol with concentrated H₂SO₄ catalyst under reflux

What type of reaction is ester formation from a carboxylic acid and alcohol?

Condensation (addition-elimination)

What are the reagents to convert a carboxylic acid to a salt?

NaOH or Na₂CO₃ at room temperature

What type of reaction is this neutralisation between a carboxylic acid and NaOH or Na₂CO₃?

Acid-base reaction

What are the reagents and conditions to convert an acyl chloride to an ester?

Alcohol under reflux

What type of reaction converts an acyl chloride to an ester?

Nucleophilic addition-elimination

What are the reagents and conditions to convert an acyl chloride to an amide?

Ammonia or amine under reflux

What type of reaction converts an acyl chloride to an amide?

Nucleophilic addition-elimination

What are the reagents and conditions to hydrolyse an ester to a carboxylic acid and alcohol?

Dilute acid (or NaOH) under reflux

What type of reaction is ester hydrolysis?

Hydrolysis

What are the reagents and conditions to convert a nitrile to a carboxylic acid?

Dilute HCl under reflux

What type of reaction is nitrile hydrolysis to a carboxylic acid?

Hydrolysis

What are the reagents and conditions to convert a nitrile to a primary amine?

H₂ with Ni catalyst (or LiAlH₄ in dry ether which is expensive)

What type of reaction converts a nitrile to a primary amine?

Reduction

What is the key difference when using NaOH aqueous versus NaOH in ethanol with a halogenoalkane?

Aqueous NaOH gives nucleophilic substitution (alcohol); Ethanolic NaOH gives elimination (alkene)

Why must KCN be used in aqueous ethanol?

It provides the CN⁻ nucleophile for substitution