Chapter 8A - Reactions involving Organic Compounds
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Substitution Reaction
When one or more atoms are substituted for another atom or a group of atoms * two products are formed
Types of substitution reactions
• Alkane + Halogen = Haloalkane + hydrogen halide • Primary Haloalkane + Metal hydroxide = primary alcohol + metal halide • Primary Haloalkane + water = primary alcohol + hydrogen halide • Primary Haloalkane + Ammonia = primary amine + ammonium halide • Primary Alcohol + Ammonia = Primary amine + water
Alkane + Halogen = Haloalkane + hydrogen halide
Reaction conditions: UV light + high temperature Redox reaction
Why do we need UV light for substitution reactions?
Provides the energy to break the covalent bonds in the halogen molecule to produce two reactive halogen atoms, each w/ an unpaired electron (free radicals)
Polysubstitution
A series of substitution reactions can occur until all hydrogen atoms have been substituted
Alkane + Halogen = Haloalkane + hydrogen halide
Reaction conditions: dilute solutions contain OH - ions & heat
Primary Haloalkane + water = primary alcohol + hydrogen halide
Reaction is very slow & requires a catalyst
Primary Haloalkane + Ammonia = primary amine + ammonium halide
Reaction conditions: concentrated ammonia (NH3) in ethanol Heat/Pressure
What are the stages of the substitution reaction between a primary haloalkane and ammonia?
Stage 1: Haloalkane is heated under pressure to form a salt Stage 2: a hydrogen atom is removed from the salt to produce the primary amine (reversible reaction hence, increasing ammonia will favour forwards reaction)
Primary Alcohol + Ammonia = Primary amine + water
Reaction conditions: alumina catalyst (Al2O3), NH3 (g) and heat
Addition Reactions
two or more molecules combine to form one product * double C=C bond in alkenes is broken, allowing other bonds to be added
Types of addition reactions
• Alkene + hydrogen halide = haloalkane • Alkene + Hydrogen = Alkane • Alkene + Halogen = Dihaloalkane • Alkene + Water vapour = Alcohol • Alkene = addition polymer with n repeating units
Alkene + hydrogen halide = haloalkane
No reaction conditions
Alkene + Hydrogen = Alkane
• hydrogenation • requires nickel/platinum catalyst (s) • redox reaction
Alkene + Halogen = Dihaloalkane
• halogenation • fluorine is too explosive • redox reaction
Alkene + Water vapour = Alcohol
Reaction conditions: H3PO4 (l), heat (300 degrees) and pressure * also called hydration
Alkene = addition polymer with n repeating units
Reaction conditions: catalyst, heat and high pressure * polymerisation
Oxidation reaction - using oxidising agents
Alcohol - Aldehyde - Carboxylic acids Strong oxidants: Potassium Permanganate/ Acidified Potassium Dichromate (aq) Reaction conditions: Heat
How can we maximise the production of aldehydes
• limit temperature • limit oxidising reagent • remove aldehyde as it is being produced by distillation
Natural oxidation of alcohols
• using O2 (g) from the air (slow) • Silver catalyst + Heat speeds the reaction up
Esterification
• reaction b/w primary alcohol and carboxylic acid • condensation reaction producing water • concentrated sulfuric acid (catalyst) • heat
Hydrolysis Reaction
Addition of water to an ester to produce a carboxylic acid and an alcohol molecule * requires heat and dilute H+
How to ensure an ester reaction and vice versa goes to completion?
Condensation: minimal water (l) Hydrolysis: excess water used (aq)
Transesterification Reactions
• biodiesel produced from triglyceride and methanol • produces 3 methyl esters (biodiesel molecules) + glycerol • NaOH and KOH as catalysts