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Edexcel organic reaction mechanisms

Edexcel organic reaction mechanisms. Click a box below to go to the mechanism. Click here for advice. Homolytic. Free Radical Substitution. Free Radical Addition. Heterolytic. Electrophilic Addition. S N 2. S N 1. Nucleophilic Substitution. Nitration. Br 2. Electrophilic Substitution.

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Edexcel organic reaction mechanisms

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  1. Edexcel organic reaction mechanisms Click a box below to go to the mechanism Click here for advice Homolytic Free Radical Substitution Free Radical Addition Heterolytic Electrophilic Addition SN2 SN1 Nucleophilic Substitution Nitration Br2 Electrophilic Substitution Alkylation Acylation Nucleophilic Addition

  2. Free radical substitution chlorination of methane i.e. homolytic breaking of covalent bonds Overall reaction equation CH4 + Cl2 CH3Cl + HCl Conditions ultra violet light excess methane to reduce further substitution

  3. Free radical substitution mechanism Cl Cl Cl Cl H Cl H3C H3C H3C H3C Cl Cl Cl H3C H Cl Cl H3C Cl H3CCl H3CCH3 CH3 ultra-violet initiation step two propagation steps termination step minor termination step

  4. Further free radical substitutions Overall reaction equations CH3Cl + Cl2 CH2Cl2 + HCl CH2Cl2 + Cl2 CHCl3 + HCl CHCl3 + Cl2 CCl4 + HCl Conditions ultra-violet light excess chlorine

  5. Free radical addition [ CH2CH2 ]n addition polymerisation of ethene i.e. homolytic breaking of covalent bonds Overall reaction equation n H2C=CH2 ethene polyethene Conditions free radical source (a species that generates free radicals that allow the polymerisation of ethene molecules)

  6. Free radical addition mechanism R R R R H2C CH2 H2C CH2 R H2C CH2 R H2C CH2 CH2CH2R H2C CH2R H2C(CH2)mR R(CH2)nCH2 R(CH2)nCH2 CH2(CH2)mR initiation step chain propagation steps Addition of H2C=CH2 repeats the same way until: termination step polyethene

  7. Electrophilic addition bromine with propene mechanism CH3CH=CH2 + Br2 CH3CHBrCH2Br 1,2-dibromopropane hydrogen bromide with but-2-ene mechanism CH3CH=CHCH3 + HBr CH3CH2CHBrCH3 2-bromobutane

  8. bromine with propene H H C C H H CH3 H C C H CH3 + Br - Br Br Br + Br Br H H - C C H CH3 Br Br Electrophilic addition mechanism reaction equation carbocation 1,2-dibromopropane

  9. hydrogen bromide with trans but-2-ene CH3 H C C H H CH3 H CH3 C C CH3 + + H H - Br Br H H - CH3 C C CH3 Br H Electrophilic addition mechanism reaction equation carbocation 2-bromobutane

  10. Nucleophilic substitution hydroxide ion with bromoethane mechanism CH3CH2Br + OH- (aqueous) CH3CH2OH + Br- ethanol hydroxide ion with 2-bromo,2-methylpropane mechanism (CH3)3CBr + OH- (aqueous) (CH3)3COH + Br- 2-methylpropan-2-ol

  11. hydroxide ion with bromoethane (SN2) H - + OH C CH3 H H - Br Br C CH3 - H OH Nucleophilic substitution mechanism ethanol SN2 reaction equation S(substitution) 2(species reacting in the slowest step) N(nucleophilic)

  12. OH- ion with 2-bromo,2-methylpropane (SN1) CH3 CH3 CH3 - + OH + C C CH3 Br C CH3 CH3 CH3 CH3 CH3 - - Br Br - OH Nucleophilic substitution mechanism 2-methylpropan-2-ol SN1 reaction equation S(substitution) 1(species reactingin the slowest step) N(nucleophilic)

  13. Nucleophilic substitution cyanide ion with iodoethane mechanism CH3CH2I (ethanol) + CN-(aq) CH3CH2CN + I- propanenitrile cyanide ion with 2-bromo,2-methylpropane mechanism (CH3)3CBr (ethanol) + CN- (aqueous) (CH3)3CCN + Br- 2,2-dimethylpropanenitrile

  14. cyanide ion with iodoethane (SN2) H - + CN C CH3 H H - I I C CH3 H - CN Nucleophilic substitution mechanism propanenitrile SN2 S(substitution) 2(species reacting in the slowest step) N(nucleophilic) reaction equation

  15. CN- ion with 2-bromo,2-methylpropane (SN1) CH3 CH3 CH3 - + CN + C C CH3 Br C CH3 CH3 CH3 CH3 CH3 - - Br Br - CN Nucleophilic substitution mechanism SN1 2,2-dimethylpropanenitrile S(substitution) 1(species reactingin the slowest step) N(nucleophilic) reaction equation

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