Mechanisms in Organic Chemistry

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Presentation transcript:

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

home Electrophilic Addition 1 – Ethene + HBr + :Br_ H C C H d+ Br H H

home Electrophilic Addition 2 – Ethene + Br2(hexane) + :Br_ C H C H Br

home Electrophilic Addition 3 – Ethene + Br2(aq) + :OH2 C H C H OH Br

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

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

Nucleophilic Substitution – SN2 Mechanism Br C H OH + _ :OH- :Br- Rate = k[C2H5Br][:OH-] home (NB Transition state)

+ home Electrophilic Substitution 1 – Nitration of benzene H2SO4 + HNO3 NO2+ + HSO4- + H2O NO2 +NO2 + NO2 H H+ home

+ home Electrophilic Substitution 2 – Bromination of benzene Br2 + AlCl3 Br+ + AlBrCl3- Br +Br + Br H HBr home AlCl3

+ home Electrophilic Substitution 3 – Alkylation of benzene CH3Cl + AlCl3 CH3+ + AlCl4- CH3 +CH3 + CH3 H HCl home AlCl3

+ home Electrophilic Substitution 4 – Acylation of benzene CH3COCl + AlCl3 CH3CO+ + AlCl4- CH3 +C O + CH3 C O H CH3 C O HCl home AlCl3

+ home Bromination of methylbenzene – ring substitution Br2 + AlBr3 Br+ + AlBr4- CH3 CH3 + H Br CH3 Br Br+ HBr home AlBr3

. CH3 + HCl . CH3 + Cl2 . CH3 + . CH3 . CH3 + . Cl home Free Radical Substitution 1 – Methane + Cl2 u.v. light Initiation 2Cl. Cl Cl Propagation CH4 + Cl. . CH3 + HCl . CH3 + Cl2 CH3Cl + Cl . Termination . CH3 + . CH3 C2H6 . CH3 + . Cl CH3Cl home

home Free Radical Addition Polymerisation of Ethene heat Initiation Propagation R C H C H R C C C H R home