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OCR organic reaction mechanisms. Click here for advice. Click a box below to go to the mechanism. AS. Free Radical Substitution. Electrophilic Addition. Nucleophilic Substitution. Electrophilic Substitution. A2. Nucleophilic Addition. Free radical substitution. chlorination of methane.
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OCR organic reaction mechanisms Click here for advice Click a box below to go to the mechanism AS Free Radical Substitution Electrophilic Addition Nucleophilic Substitution Electrophilic Substitution A2 Nucleophilic Addition
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
Free radical substitution mechanism Cl + Cl CH4 + Cl CH3 + HCl CH3 + Cl2 CH3Cl + Cl CH3 + Cl CH3 + CH3 ultra-violet Cl2 initiation step two propagation steps termination step CH3Cl minor termination step CH3CH3
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
Electrophilic addition bromine with ethene Overall reaction equation CH2=CH2 + Br2 CH2BrCH2Br 1,2-dibromoethane mechanism
bromine with ethene H H C C H H H H C C H H + Br - Br Br Br + Br Br H H - C C H H Br Br Electrophilic addition mechanism carbocation 1,2-dibromoethane reaction equation
Nucleophilic substitution water with bromoethane mechanism CH3CH2Br + H2O CH3CH2OH + HBr ethanol hydroxide ion with bromoethane mechanism CH3CH2Br + OH- (aqueous) CH3CH2OH + Br- ethanol
water with bromoethane H - + OH C CH3 H + H O H C H CH3 Br C H CH3 H H O - Br H H H Br Nucleophilic substitution mechanism ethanol reaction equation
hydroxide ion with bromoethane H - + OH C CH3 H H - Br Br C CH3 - H OH Nucleophilic substitution mechanism ethanol reaction equation
Electrophilic Substitution Nitration of benzene C6H6 + HNO3 C6H5NO2 + H2O Conditions / Reagents concentrated HNO3 and concentrated H2SO4 50oC mechanism
electrophilic substitution mechanism (nitration) NO2 + 1. Formation of NO2 H + + NO2 O SO3H- + NO2 NO2 H O SO3H the nitronium ion HNO3 + 2H2SO4 + H3O+ + 2HSO4- 2. Electrophilic attack on benzene 3. Forming the product and re-forming the catalyst reaction equation
Nucleophilic Addition HCN + OH- addition of hydrogen cyanide to carbonyls to form hydroxynitriles + HCN RCOR RC(OH)(CN)R RCH(OH)CN + HCN RCHO Conditions / Reagents HCN (aq) andNaOH(aq) to form the CN- nucleophile CN- + H2O Room temperature and pressure
Nucleophilic Addition Mechanism C N - O + O O H H CN CN C CH3 C CN CH3 C CN CH3 CH3 CH3 CH3 CN hydrogen cyanide with propanone + HCN CH3COCH3 CH3C(OH)(CN)CH3 HCN / NaOH (aq) is a source of cyanide ions 2-hydroxy-2-methylpropanenitrile
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References Steve Lewis for the Royal Society of Chemistry