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SL Reaction pathways

SL Reaction pathways. Deduce reaction pathway given the starting materials and the product, e.g : CH 3 CH 2 OH CH 3 CH 2 CHO Conversions with more than two stages will not be assessed. Reagents, conditions and equations should be included

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SL Reaction pathways

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  1. SL Reactionpathways • Deduce reaction pathway given the starting materials and the product, e.g: CH3CH2OH CH3CH2CHO • Conversions with more than two stages will not be assessed. Reagents, conditions and equations should be included • The compound and reaction types in this topic are summarized in the schemes on the next slides K2Cr2O7

  2. propanoicacid oxidation polypropene propanal oxidation (M) polyaddition 1-propanol +H2O addition propene (M) substitution +OH- addition +HCl addition 1-chloro-propane +H2 (M) substitution via radical reaction 1,2-dichloro-propane (M) substitution via radical reaction propane (M) further radical substitution to tri- and tetra-chloropropane

  3. propanoicacid Oxidation of primary alcohol with acidified K2Cr2O7. Reflux to get the product propanal polypropene Oxidation of primary alcohol with acidified K2Cr2O7. Distillation to get the product Poly-addition. Radical mechanism. Initiation, prolongation and termination 1-propanol Addition reaction. Hydrogen halide (HCl), spontaneous at STP (M) substitution reaction with NaOH; SN1 or SN2 propene 1-chloro-propane Addition reaction. H2and Ni-catalyst (M) substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light (M) substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light 1,2-dichloro-propane propane (M) further radical substitution to tri- and tetra-chloropropane

  4. carboxylicacid polyalkene oxidation aldehyde (M) polyaddition oxidation primaryalcohol alkene (M) substitution +OH- addition +HCl addition +Cl2 chloroalkane (M) substitution via radical reaction (M) substitution via radical reaction dichloroalkane alkane (M) further radical substitution to tri- and tetra-chloropropane

  5. What is formed? oxidation oxidation (M) polyaddition addition +HCl (M) substitution +OH- addition 1-chloro-butane +H2 (M) substitution via radical reaction (M) substitution via radical reaction butane (M) further radical substitution to tri- and tetra-chloropropane

  6. propanone polypropene oxidation (M) polyaddition 2-propanol 1-propene addition +OH- (M) substitution +HCl addition +H2 2-chloro-propane 1,2-dichloro-propane (M) substitution via radical reaction (M) substitution via radical reaction propane (M) further radical substitution to tri- and tetra- chloropropane

  7. propanone Oxidation of secondary alcohol with acidified K2Cr2O7 polypropene 2-propanol (M) polyaddition (M) substitution +OH- addition 1-propene 2-chloro-propane +HCl addition (M) substitution via radical reaction +Cl2 (M) substitution via radical reaction 1,2-dichloro-propane propane (M) further radical substitution to tri- and tetra chloropropane

  8. ketone polyalkene oxidation (M) polyaddition secondary alcohol addition (M) substitution +OH- +HCl alkene secondary chloroalkane addition +H2 (M) substitution via radical reaction (M) substitution via radical reaction alkane dichloroalkane (M) further radical substitution to tri- and tetra chloropropane

  9. What is formed? oxidation substitution +OH- 2-chloro-butane substitution via radical reaction butane

  10. Draw structuralformulaofreactants and products, namethem and givereactionpathway K2Cr2O7 CH3CH2CHO H2 CH3CH=CHCH3 NaOH K2Cr2O7 CH3Br UV-light, Cl2 CH3CH3 HI CH3CH=CHCH2CH3

  11. Answers K2Cr2O7 CH3CH2CHO CH3CH2COOH oxidation propanal propanoicacid H2 CH3CH=CHCH3 addition CH3CH2CH2CH3 butane 2-butene NaOH K2Cr2O7 CH3Br CH3OH CH2O substitution oxidation methylbromide methanal methanol UV-light, Cl2 CH3CH3 radical substitution CH2ClCH3 ethane chloroethane HI CH3CH=CHCH2CH3 addition CH3CHICH2CH2CH3 2-pentene 2-iodopentane

  12. 1-3. Substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light. 4. Addition reaction. Hydrogen halide, spontaneous at STP 5. Addition reaction. H2 and Ni-catalyst 6. Addition reaction. Halogene, spontaneous at STP 7. Poly-addition. Radical mechanism. Initiation, prolongation and termination 8. Substitution reaction with NaOH; SN1 or SN2 9. Oxidation of primary alcohol with acidified K2Cr2O7. Distillation to get the product 10. Oxidation of primary alcohol with acidified K2Cr2O7. Reflux to get the product 11. Oxidation of secondary alcohol with acidified K2Cr2O7

  13. HL Reaction pathways (M) Substitution reaction. SN1 or SN2 CN- 1-chloro-propane butanenitrile propene (M) Elimination reaction. Hot, concentrated and reflux Reduction with H2 and Ni-catalyst • (M) Substitution reaction. • SN1 or SN2 • NH3 1-propanol propylamine, butylamine Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester). Equilibrium reaction. Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction. propanoicacid 1-propyl propanoate propyl amide

  14. HL Reaction pathways nitrile alkene (M) Substitution CN- (M) Elimination Reduction chloropropane (M) Substitution alcohol amine Condensation carboxylicacid Condensation ester amide

  15. What is formed? substitutionCN- 1-chloro-butane elimination reduction H2 substitution NH3 1-butanol Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester). Equilibrium reaction. Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction. butanoicacid

  16. HL Reaction pathways alkene 1. Elimination reaction. Hot, concentrated and reflux 2. Substitution reaction. SN1 or SN2 3. Substitution reaction. SN1 or SN2. (Can be substituted up 4 times to a quarternaryammonum salt) 4. Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester). Equilibrium reaction. 5. Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction. 6. Nitrile to amin: Reduction with H2 and Ni-catalyst 6

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