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Mechanisms in Organic Chemistry
Alkenes Aldehydes or ketones Halogenoalkanes Arenes Alkanes Electrophilic Addition HBr, Br2,Br2(aq) Free Radical Polymerisation Nucleophilic Addition Nucleophilic Substitution SN1 SN2 Electrophilic Substitution Free Radical Substitution
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home Electrophilic Addition 1 – Ethene + HBr + :Br_ H C C H d+ Br H H
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home Electrophilic Addition 2 – Ethene + Br2(hexane) + :Br_ C H C H Br
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home Electrophilic Addition 3 – Ethene + Br2(aq) + :OH2 C H C H OH Br
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home C :OH H3C H CN C O H3C H H+ C :O_ H3C H CN :CN_
Nucleophilic Addition – Reaction of HCN with Carbonyls d+ d_ C :OH H3C H CN C O H3C H H+ C :O_ H3C H CN :CN_ home
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home Nucleophilic Substitution – SN1 Mechanism + Rate = k[C4H9Br] C
H3C OH C CH3 H3C + C CH3 H3C Br d+ d- :OH- :Br- Rate = k[C4H9Br] home
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Nucleophilic Substitution – SN2 Mechanism
Br C H OH + _ :OH- :Br- Rate = k[C2H5Br][:OH-] home (NB Transition state)
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+ home Electrophilic Substitution 1 – Nitration of benzene
H2SO HNO3 NO HSO H2O NO2 +NO2 + NO2 H H+ home
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+ home Electrophilic Substitution 2 – Bromination of benzene
Br AlCl3 Br AlBrCl3- Br +Br + Br H HBr home AlCl3
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+ home Electrophilic Substitution 3 – Alkylation of benzene
CH3Cl AlCl3 CH AlCl4- CH3 +CH3 + CH3 H HCl home AlCl3
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+ home Electrophilic Substitution 4 – Acylation of benzene
CH3COCl AlCl3 CH3CO AlCl4- CH3 +C O + CH3 C O H CH3 C O HCl home AlCl3
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+ home Bromination of methylbenzene – ring substitution
Br AlBr3 Br AlBr4- CH3 CH3 + H Br CH3 Br Br+ HBr home AlBr3
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. CH3 + HCl . CH3 + Cl2 . CH3 + . CH3 . CH3 + . Cl home
Free Radical Substitution 1 – Methane + Cl2 u.v. light Initiation 2Cl. Cl Cl Propagation CH Cl. . CH HCl . CH Cl2 CH3Cl + Cl . Termination . CH3 + . CH3 C2H6 . CH Cl CH3Cl home
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home Free Radical Addition Polymerisation of Ethene heat Initiation
Propagation R C H C H R C C C H R home
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