organic synthesis

• To convert an alkane into a halogenoalkane:

  • Reagent: Chlorine or bromine
  • Conditions: UV light
  • Mechanism name: Free radical substitution

  
• To turn a halogenoalkane into an alkene:

  • Reagent: Ethanolic potassium hydroxide
  • Conditions: Heated under reflux
  • Name of reaction: Elimination

  
• To turn a halogenoalkane into a nitrile:

  • Reagent: Potassium cyanide
  • Conditions: Ethanolic/water mixture (so it doesn't dissociate) and heated under reflux
  • Name of reaction: Nucleophilic substitution

  
• To turn a halogenoalkane into a primary amine:

  • Reagent: EXCESS concentrated ammonia (so more of the primary amines are made rather than secondary or tertiary)
  • Conditions: Ethanolic, heated under reflux in a pressurised sealed container (so it doesn't dissociate)
  • Name of reaction: Nucleophilic substitution

  
• To turn a halogenoalkane into an alcohol:

  • Reagent: Potassium/sodium hydroxide
  • Conditions: AQUEOUS and heated under reflux
  • Name of reaction: Nucleophilic substitution

  
• To turn a halogenoalkane into an alkene:

  • Reagent: Potassium hydroxide
  • Conditions: Ethanolic and done under reflux
  • Name of reaction: Elimination

  
• To turn an alkene into a dihalogenoalkane:

  • Reagent: Bromine/chlorine
  • Conditions: Room temperature
  • Name of reaction: Electrophilic addition

  
• To turn a dihalogenoalkane into a diol:

  • Reagent: Potassium hydroxide
  • Conditions: Aqueous, heat under reflux
  • Name of reaction: Nucleophilic substitution

  (mechanism is the same as a normal haloalkane)

  
• To turn an alkene into a poly(alkene)

  Reagent: Alkene (acts as a monomer)

  Conditions: High pressure and a catalyst

  No mechanism required
• To turn an alkene into an alcohol (using an acid catalyst):

  • Reagent: Ethene/Alkene
  • Conditions: High temperature (300C), high pressure (7100 kPa) and CONCENTRATED phosphoric acid catalyst
  • Name of reaction: Hydration/addition

  
• To turn an alkene into an alkyl hydrogensulfate:

  • Reagent: CONCENTRATED sulfuric acid
  • Conditions: Room temperature
  • Type of reaction: Electrophilic addition

  
• To turn an alkyl hydrogensulfate into an alcohol:

  • Reagent: Water
  • Conditions: Warm mixture
  • Type of reaction: Hydrolysis

  
• To turn a primary alcohol into an aldehyde:

  • Reagent: LIMITED concentrated potassium dichromate and sulfuric acid
  • Conditions: Heated and distilled when formed
  • Type of reaction: Partial oxidation
• To turn a primary alcohol into a carboxylic acid:

  • Reagent: EXCESS concentrated potassium dichromate and sulfuric acid
  • Conditions: Heated under reflux
  • Type of reaction: Oxidation
• To turn a secondary alcohol into a ketone:

  • Reagent: Concentrated potassium dichromate and sulfuric acid
  • Conditions: Heated under reflux
  • Type of reaction: Oxidation
• To turn an aldehyde/ketone into an alcohol:

  • Reagent: NaBH₄ in aqueous ethanol solution
  • Conditions: Room temperature
  • Type of reaction: Reduction/nucleophilic addition

  Catalytic hydrogenation using hydrogen and a nickel catalyst at a high pressure also achieves this

  
• To turn an aldehyde/ketone into a hydroxynitrile:

  • Reagent: Sodium cyanide and dilute sulfuric acid
  • Conditions: Room temperature
  • Type of reaction: Nucleophilic addition

  
• To form an ester:

  • Reagent: Carboxylic acid and alcohol
  • Conditions: Concentrated sulfuric acid and heated
  • Type of reaction: Esterification

  This reaction is not very efficient, as the reaction is very slow and the reaction is also reversible
• To form a secondary amide:

  • Reagent: Acyl chloride/acid anhydride and primary amine
  • Conditions: Room temperature
  • Type of reaction: Nucleophilic addition-elimination

  
• To form a primary amide:

  • Reagent: Acyl chloride/acid anhydride and ammonia
  • Conditions: Room temperature
  • Type of reaction: Nucleophilic addition-elimination

  
• To form a carboxylic acid from an acyl chloride/acid anhydride:

  • Reagent: Acyl chloride/acid anhydride and water
  • Conditions: Room temperature
  • Name of reaction: Nucleophilic addition-elimination

  
• To form an ester using an acyl chloride/acid anhydride:

  • Reagent: Acyl chloride/acid anhydride and alcohol
  • Conditions: Room temperature
  • Name of reaction: Esterification

  This reaction is much more efficient for making esters compared to carboxylic acids. This is due to the reaction being far quicker, and the reaction is non-reversible

  
• Hydrolysing esters using acids:

  • Reagent: Dilute hydrochloric acid and ester
  • Conditions: Heated under reflux
  • Products: Carboxylic acid and alcohol

  This reaction is reversible, and so the product yield isn't very high.

  
• Hydrolysing esters using a base:

  • Reagent: Dilute sodium hydroxide and ester
  • Conditions: Heated under reflux
  • Products: Carboxylate salt and alcohol

  This reaction is non-reversible and so has a higher yield. Adding a strong acid to the mixture turns the carboxylate salt into a carboxylic acid

  
• To form an alkane from an alkene:

  • Reagent: Hydrogen gas in the presence of a nickel catalyst
  • Conditions: High temperatures and pressure
  • Name of reaction: Hydrogenation
• To turn a halogenoalkane into an alcohol:

  • Reagent: Aqueous potassium hydroxide
  • Conditions: Heated under reflux
  • Name of reaction: Nucleophilic substitution

  
• To turn a halogenoalkane into a nitrile:

  • Reagent: Hydrogen/potassium cyanide dissolved in ethanol/water solution
  • Conditions: Heated under reflux
  • Name of reaction: Nucleophilic substitution

  
• To turn a halogenoalkane into an amine:

  • Reagent: Ammonia dissolved in ethanol
  • Conditions: Heated under reflux in a sealed container
  • Name of reaction: Nucleophilic substitution

  Using an excess of ammonia increases the yield of the amine, as if the ammonia is limited then further substitutions between the halogenoalkanes and amines can occur

  
• To turn a nitrile into an amine:

  • Reagent: LiAlH₄
  • Conditions: Ether solution/hydrogen gas using a nickel catalyst
  • Name of reaction: Reduction