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Aliphatic Organic Reactions

Aliphatic Organic Reactions. Substitution. Addition. Reduction. Oxidation. Elimination. K 2 Cr 2 O 7 H 2 SO 4 (aq). Condensation. Hydrolysis. Reflux. [O]. Amide. Carboxylate salt. RCOOH. RTP. RNH 2. CH 3 CONHR’. NaOH (aq). CH 3 COO - Na +. NaOH (aq). RTP. RTP. [H].

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Aliphatic Organic Reactions

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  1. Aliphatic Organic Reactions Substitution Addition Reduction Oxidation Elimination K2Cr2O7 H2SO4 (aq) Condensation Hydrolysis Reflux [O] Amide Carboxylate salt RCOOH RTP RNH2 CH3CONHR’ NaOH (aq) CH3COO-Na+ NaOH (aq) RTP RTP [H] Reflux LiAlH4 (ether) HCl (aq) warm CH3CH2CH2NH2 Reflux CH3CH2COOH Amine Nitrile Carboxylic Acid Acid anhydride CH3CH2NH2 CH3CH2CN CH3COOH (CH3CO)2O ROH NaBH4(aq) Conc NH3 (alc) KCN (alc) ROH Heat Reflux SOCl2 Reflux Reflux [H] H2SO4 Cat Heat Radical substitution Alkane Halogenoalkane Aldehyde Acyl Chloride Ester Cl2 UV light CH3CH3 CH3CH2Br CH3CHO CH3COCl CH3COOR ROH RTP NaOH (alc) NaOH (aq) RCOOCH2CH3 H2 (g) Ketone Reflux Reflux NaBH4(aq) K2Cr2O7 H2SO4 (aq) Hydrogenation Ni Cat HBr HBr Reflux CH3COCH3 150 o C 500KPa Distil [H] K2Cr2O7 H2SO4 (aq) RTP Reflux [O] Heat Alkene Alcohol Reflux Primary Secondary [O] RCOOH Conc H2SO4 Reflux CH2=CH2 CH3CH2OH CH3 CH(OH)CH3 RTP Dehydration H2SO4 Cat Br2 H2O(g) 300o C Reflux H3PO4 cat H2O 7MPa H2SO4 NaOH(aq) or H2SO4(aq) H2O Reflux Hydration warm dihalogenoalkane Alkyl hydrogensulphate CH2BrCH2Br CH2(HSO4)CH3

  2. Aromatic Organic Reactions NO2 NH3+Cl- NH2 [ + NN ] Cl- O-Na+ [H] diazotization Sn NaNO2 NaOH(aq) Conc HCl HCl (aq) Substitution Reflux <5oC Reduction Acid-Base nitrobenzene phenylammonium chloride phenylamine diazonium salt Sodium phenoxide Nitration OH Conc H2SO4 NaOH(aq) or Na (s) Coupling reaction Conc HNO3 <5oC <55oC azo group RTP NaOH(aq) N=N OH <5oC HNO3(aq) RTP Br2(aq) RTP Benzene Azo dye Phenol Br2 FeBr3 Reflux Cl2 AlCl3 Reflux OH OH O2N NO2 Br Br Br Cl Halogenations White solid Chris Wright 2012 NO2 Br bromobenzene chlorobenzene 2,4,6-trinitrophenol 2,4,6-tribromophenol

  3. Aliphatic Organic Reactions K2Cr2O7 H2SO4 (aq) Reflux [O] Amide Carboxylate salt RCOOH RTP RNH2 CH3CONHR’ NaOH (aq) CH3COO-Na+ NaOH (aq) RTP RTP Substitution [H] Reflux LiAlH4 (ether) Addition HCl (aq) warm CH3CH2CH2NH2 Reflux CH3CH2COOH Reduction Amine Nitrile Carboxylic Acid Acid anhydride Oxidation CH3CH2NH2 CH3CH2CN CH3COOH (CH3CO)2O Elimination ROH NaBH4(aq) Condensation Conc NH3 (alc) KCN (alc) ROH Heat Reflux SOCl2 Hydrolysis Reflux Reflux [H] H2SO4 Cat Heat Radical substitution Alkane Halogenoalkane Aldehyde Acyl Chloride Ester Cl2 UV light CH3CH3 CH3CH2Br CH3CHO CH3COCl CH3COOR ROH RTP NaOH (alc) NaOH (aq) RCOOCH2CH3 H2 (g) Ketone Reflux Reflux NaBH4(aq) K2Cr2O7 H2SO4 (aq) Hydrogenation Ni Cat HBr HBr Reflux CH3COCH3 150 o C 500KPa Distil [H] K2Cr2O7 H2SO4 (aq) RTP Reflux [O] Heat Alkene Alcohol Reflux Primary Secondary [O] RCOOH Conc H2SO4 Reflux CH2=CH2 CH3CH2OH CH3 CH(OH)CH3 RTP Dehydration H2SO4 Cat Br2 H2O(g) 300o C Reflux H3PO4 cat H2O 7MPa H2SO4 NaOH(aq) or H2SO4(aq) H2O Reflux Hydration warm dihalogenoalkane Alkyl hydrogensulphate CH2BrCH2Br CH2(HSO4)CH3

  4. Aliphatic Organic Reactions Amide Carboxylate salt CH3CONHR’ CH3COO-Na+ Amine Nitrile Carboxylic Acid Acid anhydride CH3CH2NH2 CH3CH2CN CH3COOH (CH3CO)2O Alkane Halogenoalkane Aldehyde Acyl Chloride Ester CH3CH3 CH3CH2Br CH3CHO CH3COCl CH3COOR Ketone CH3COCH3 Alkene Alcohol Primary Secondary CH2=CH2 CH3CH2OH CH3 CH(OH)CH3 dihalogenoalkane Alkyl hydrogensulphate CH2BrCH2Br CH2(HSO4)CH3

  5. Aromatic Organic Reactions NO2 NH3+Cl- NH2 [ + NN ] Cl- O-Na+ [H] Substitution Reduction Acid-Base Add 1) Names 2) Reagents 3) Conditions OH N=N OH OH OH O2N NO2 Br Br Cl Br White solid NO2 Br Chris Wright 2013

  6. Hydrolysis of Esters and Amides O O = = R – C – O - R – C – O – H Ester (sec) Amide O RCOOR’ O RCONHR’ = = H R – C –N – R’ R – C –O – R’ Acid hydrolysis e.g. HCl + Reflux + Acid hydrolysis e.g. HCl + Reflux H – N – R’ H – N – R’ H H+ OH- H+ H+ H+ OH- H H O = R – C – O – H H – O – R’ R’NH3+ RCOOH R’OH RCOOH Carboxylic acid Carboxylic acid Alcohol Salt of Amine Ester (sec) Amide O O RCOOR’ RCONHR’ = = R – C –O – R’ R – C –N – R’ Alkaline hydrolysis e.g. NaOH + Reflux Alkaline hydrolysis e.g. NaOH + Reflux H H+ OH- OH- OH- H+ OH- O = R – C – O - H – O – R’ H – N – R’ H R’OH RCOO- RCOO- R’NH2 Carboxylate salt Alcohol Carboxylate salt Amine

  7. Hydrolysis of Esters and Amides Ester (sec) Amide O RCOOR’ O RCONHR’ = = R – C –N – R’ R – C –O – R’ Acid hydrolysis e.g. HCl + Reflux Acid hydrolysis e.g. HCl + Reflux H H+ OH- H+ H+ H+ OH- Ester (sec) Amide O O RCOOR’ RCONHR’ = = R – C –O – R’ R – C –N – R’ Alkaline hydrolysis e.g. NaOH + Reflux Alkaline hydrolysis e.g. NaOH + Reflux H H+ OH- OH- OH- H+ OH- O

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