Chapter 28: Further Synthetic Routes
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What products can benzene react to form?
• Nitrobenzene • Halobenzene • Alkylbenzene • Phenylketone
Benzene to nitrobenzene. Reactants, conditions and mechanism if applicable.
• Reactants: concentrated nitric acid and benzene • Conditions: concentrated sulfuric acid catalyst • Mechanism: electrophilic substitution • HNO3 (conc) + H2SO4 (conc) -> NO2+ + HSO4- + H2O • C6H6 + NO2+ -> C6H5NO2 + H+ • H+ + HSO4- -> H2SO4
Benzene to bromobenzene. Reactants, conditions and mechanism if applicable.
• Reactants: bromine and benzene • Conditions: halogen carrier catalyst • Mechanism: electrophilic substitution • Br2 + FeBr3 -> FeBr4- + Br+ • C6H6 + Br+ -> C6H5Br + H+ • H+ + FeBr4- -> FeBr3 + HBr
Benzene to alkylbenzene. Reactants, conditions and mechanism if applicable.
• Reactants: haloalkane and benzene • Conditions: halogen carrier catalyst • Mechanism: electrophilic substitution • Benzene + haloalkane -> alkyl benzene + hydrogen halide
Benzene to phenylketone. Reactants, conditions and mechanism if applicable.
• Reactants: acyl chloride and benzene • Conditions: iron (III) chloride/ aluminium chloride • Mechanism: electrophilic substitution • Benzene + acyl chloride -> phenylketone + hydrogen chloride
What can phenol react to form?
• 2,4,6-tribromophenol • Nitrophenol • Metal phenoxide • Ester
Phenol to 2,4,6-tribromophenol. Reactants, conditions and mechanism if applicable. Give 2 extra details.
• Reactants: phenol and bromine water • Conditions: room temperature, no catalyst • Mechanism: electrophilic substitution • C6H5OH + 3Br2 -> 2,4,6-tribromophenol + 3HBr • Bromine water is decolourised • A white precipitate (2,4,6-tribromophenol) is formed
Phenol to nitrophenol. Reactants, conditions and mechanism if applicable. Give 1 extra detail.
• Reactants: phenol and dilute nitric acid • Conditions: room temperature, no catalyst • Mechanism: electrophilic substitution • Phenol + dilute nitric acid -> 2-nitrophenol/ 4-nitrophenol + water • A mixture of 2-nitrophenol and 4-nitrophenol is formed
Phenol to sodium phenoxide. Reactants, conditions and mechanism if applicable. Give 1 extra detail.
• Reactants: phenol and sodium hydroxide • Conditions: room temperature, no catalyst • Products: sodium phenoxide and water • Neutralisation
Phenol to ester. Reactants, conditions and mechanism if applicable. Give 1 extra detail.
• Reactants: phenol and acid anhydride/ acyl chloride • Conditions: room temperature, no catalyst • Products: ester and carboxylic acid/ hydrogen chloride • Carboxylic acids are not reactive enough to esterify phenol
What can aldehydes react to form?
• Carboxylic acids • Primary alcohols • Hydroxynitriles
Aldehyde to carboxylic acid. Reactants, conditions and mechanism if applicable. Give 1 extra detail.
• Reactants: aldehyde and [O] • Conditions: heat under reflux, K2Cr2O7/ H2SO4 • Water is not formed as it was already formed in the step going from an alcohol to an aldehyde
Aldehyde to primary alcohol. Reactants, conditions and mechanism if applicable.
• Reactants: aldehyde and 2[H] • Conditions: NaBH4/ H2O • Mechanism: nucleophilic addition
Aldehyde to hydroxynitrile. Reactants, conditions and mechanism if applicable.
• Reactants: aldehyde and HCN • Conditions: NaCN/ H2SO4 • Mechanism: nucleophilic addition
What can ketones react to form?
• Secondary alcohols • Hydroxynitriles
Ketone to secondary alcohol. Reactants, conditions and mechanism if applicable.
• Reactants: ketone and 2[H] • Conditions: NaBH4/ H2O • Mechanism: nucleophilic addition
Ketone to hydroxynitrile. Reactants, conditions and mechanism if applicable.
• Reactants: ketone and HCN • Conditions: NaCN/ H2SO4 • Mechanism: nucleophilic addition
What can carboxylic acids react to form?
• Esters • Acyl chlorides
Carboxylic acid to ester. Reactants, conditions and mechanism if applicable. Give 1 extra detail.
• Reactants: carboxylic acid and alcohol • Conditions: H2SO4, heat • Products: ester and water • This reaction is esterification
Carboxylic acid to acyl chloride. Reactants, conditions and mechanism if applicable.
• Reactants: carboxylic acid and SOCl2 (thionyl chloride) • Products: acyl chloride, sulfur dioxide and hydrogen chloride • Conditions: room temperature, no catalyst
What can esters react to form?
• Carboxylic acid • Carboxylate ion/ carboxylate salt
Ester to carboxylic acid. Reactants, conditions and mechanism if applicable. Give 2 extra details.
• Reactants: ester and water • Conditions: heat under reflux, aqueous H2SO4 • Products: carboxylic acid and alcohol • This reaction is known as hydrolysis • It is reversible (esterification)
Ester to carboxylate ion/ carboxylate salt. Reactants, conditions and mechanism if applicable. Give 2 extra details.
• Reactants: ester and hydroxide ion/ NaOH • Conditions: heat under reflux, aqueous NaOH • Products: carboxylate ion/ sodium carboxylate and alcohol • This reaction is known as hydrolysis • It is irreversible
What can acyl chlorides react to form? Which mechanism do acyl chlorides undergo?
• Esters • Carboxylic acids • Primary amides • Secondary amides • Nucleophilic addition-elimination