1 ORGANIC CHEMISTRY BIBLE OF CHEMICAL REACTIONS This bible includes chemical reactions that are covered in the ZIMSEC Advanced Level syllabus. Reactions of Alkanes Type of reaction Combustion Free radical substitution reagents Oxygen (excess) Oxygen (limited) r.t.p. Conditions Main products CO2 and H2O Example 2C2H6 + 7O2 4CO2 + 6H2O CO and H2O 2C2H6 + 5O2 4CO + 6H2O Heat Ultraviolet light Halogenoalkanes C2H6 Cl2 C2H5Cl + HCl C2H5Cl + Cl2 C2H4Cl2 + HCl Conditions 300℃ 60 atm r.t.p. Main products Alcohol Halogenoalkane C2H4 +HCl C2H5Cl chloroethane r.t.p. Halogenoalkane C2H4 + Cl2 CH2Cl-CH2Cl C2H4 + H2 C2H6 Reactions of Alkenes Type of reaction Electrophilic addition Catalytic addition Oxidation reagents Steam conc H3PO4 Hydrogen halide Halogen Hydrogen Nickel cat. Alkaline dil. KMnO4 140 ℃ r.t.p Example C2H2 + H2O C2H5OH ethane Alkane Alcohol (diol) ethanol 1,2-dichloroethane ethane C2H4 + [O] + H2O CH2OH-CH2OH ethan-1,2-diol Alkaline conc. KMnO4 Heat Ketones Carboxylic acids CH3 C CH CH CH2 + 7[O] 4,4-dimethyl 1,3-diene CH3 Addition polymerization CH3 O O C O + C C CH3 OH OH propanone ethanedioic acid (oxalic acid) n(C2H4) (C2H4)n ethene polythene Monomers + Catalyst Heat Pressure Polymer reagents Halogen + FeX3/Fe Conditions r.t.p. Main products Example Halogenobenzene C6H6 +Br2 conc HNO3 conc H2SO4 Reflux below 60℃ Reactions of Arenes Benzene Type of reaction Electrophilic substitution (Halogenation) Electrophilic substitution (Nitration) M. Kole benzene Nitrobenzene C6H6 + HNO3 C6H5Br + HBr bromobenzene C6H5NO2 + H2O nitrobenzene 2 Elimination (Friedel-Crafts) Haloalkane AlCl3 cat r.t.p. reagents Halogen Conditions r.t.p. Alkylbenzene C6H6 + CH3Cl C6H5CH3 +HCl methylbenzene Methylbenzene Type of reaction Electrophilic substitution (Halogenation) Electrophilic substitution (Nitration) Free radical substitution Oxidation Main products Halogenomethylbenzene conc. HNO3 conc.H2SO4 30 ℃ Halogen r.t.p. uv light r.t.p. Halogenoarene Example 2C6H5CH3 + 2Br2 2 2C6H4(Br)CH3 + 2-bromomethylbenzene + 4-bromomethylbenzene nitromethylbenzene 2C6H5CH3 + 2HNO3 2H2O 2C6H4(NO2)CH3 + 2-nitromethylbenzene + 4-nitromethylbenzene Aldehyde C6H5CH3 + Cl2 C6H5CH2Cl + Cl2 C6H5CH3 + 2[O] C6H5CH2Cl +HCl C6H5CHCl2 + HCl C6H5CHO + H2O Heat Carboxylic acid C6H5CH3 + 3[O] C6H5COOH + H2O reagents H2O NaOH (aq) Conditions Boil Main products Alcohol Example C2H5Cl + NaOH C2H5OH + NaOH KCN in alcohol Reflux CH3CH2I + KCN CH3CH2CN + KI iodoethane propanenitrile Excess conc. NH3 Heat NaOH in alcohol NaOH HNO3 AgNO3 Boil dil. acidified KMnO4 dil. acidified KMnO4 Reactions of Halogenoalkanes Type of reaction Nucleophilic substitution (Hydrolysis) Nucleophilic substitution (formation of nitrile) Nucleophilic substitution (formation of amine) Elimination Test for halogenoalkane chloroethane Boil with NaOH, add HNO3 then AgNO3 Nitrile Amine Alkene Silver halide ethanol CH3CH2Br + NH3 CH3CH2NH2 + HBr bromoethane ethanamine CH3CH2Br + NaOH CH2=CH2 + HBr - CH3CH2Br + OH Ag+(aq) + Br-(aq) ethene CH3CH2OH + Br- ethanol AgBr (s) silver bromide AgCl (white) AgBr (cream) AgI (yellow) M. Kole 3 Reactions of hydroxyl compounds Alcohols Type of reaction Combustion Nucleophilic substitution (with halide) Displacement Oxidation (primary alcohol) Type of reaction Oxidation (secondary alcohol) Elimination (dehydration) Elimination/ Condensation (esterification) reagents Oxygen Hydrogen halide (HX) (from NaX + H2SO4) Phosphorus halide (PX) Sodium K2Cr2O7/H+ Conditions Heat Heat in conc. H3PO4 Main products CO2 , H2O Halogenoalkane r.t.p. Halogenoalkane r.t.p. Reflux Example CH3CH2OH + 3O2 CH3CH2OH + HBr 2CO2 + 3H2O CH3CH2Br + H2O 3CH3CH2OH + PI3 3CH3CH2I + H3PO3 CH3CH2OH + Na CH3CH2OH + [O] CH3CH2ONa + 1/2H2 CH3CHO +H2O ethanol Sodium alkoxide Aldehyde bromoethane iodoethane ethanal reagents K2Cr2O7/H+ Conditions Reflux conc. H2SO4 cat. or Al2O3 cat. Carboxylic acid conc. H2SO4 cat. 170 ℃ reagents Sodium metal Acyl chloride Conditions r.t.p Main products Ketone Example CH3CH(OH)CH3 + [O] CH3COCH3 + propan-2-ol Heat Heat Alkene Ester propanone H2O CH3CH2OH CH2=CH2 + H2O ethanol ethene CH3CH2OH + CH3COOH ethanol ethanoic acid CH3COOCH2CH3 + H2O ethylethanoate Phenols Type of reaction Displacement Elimination (acylation) Neutralization Electrophilic substitution (bromination) Electrophilic substitution (nitration) M. Kole Main products Sodium phenoxide Example C6H5OH +Na phenol r.t.p. Ester CH3COCl + C6H5OH ethanoyl chloride Base Bromine, Br2 r.t.p r.t.p. Metal ethoxide 2,4,6tribromophenol Nitric acid, HNO3 r.t.p. Nitrophenol + HCl C6H5OH + NaOH C6H5OH + 3Br2 C6H5OH + 2HNO3 2C6H4OHNO2 2-nitrophenol and 4-nitrophenol C6H5O-Na+ sodium phenoxide H3COOC6H5 phenylethanoate C6H5O-Na+ + H2O C6H2Br3OH + 3HBr C6H5OH + 4 Reactions of carboxylic acids Type of reaction reagents Base Neutralization Conditions r.t.p. Carbonate Displacement Elimination/ condensation (esterification) Formation of acyl chlorides Main products Salt and water Sodium metal r.t.p. Salt and carbon dioxide Salt and hydrogen Example CH3COOH + NaOH ethanoic acid CH3COONa + H2O sodium ethanoate water CH3COOH + NaCO3 CH3COONa + CO2 CH3COOH + Na CH3COONa + 1/2H2 See alcohols PCl5 Heat Acyl chloride PCl3 SOCl2 Heat r.t.p. CH3COOH + PCl5 CH3COCl + POCl3 + HCl phosphorus pentachloride ethanoyl chloride CH3COOH + PCl3 CH3COCl + H3PO4 CH3COOH + SOCl2 CH3COCl + SO2 + HCl Reactions of acyl chlorides Type of reaction Hydrolysis Elimination (esterification) reagents Water, H2O Alcohol Conditions r.t.p. r.t.p. Main products Carboxylic acid Ester Example CH3COCl + H2O CH3COOH + HCl CH3COCl + CH3CH2OH CH3COOCH2CH3 + HCl ethyl ethanoate Phenol in alkaline solution r.t.p. Ester CH3COCl + C6H5OH HCl CH3COOC6H5 + phenylethanoate Reactions of carbonyl compounds Aldehydes Type of reaction Nucleophilic addition reagents Conditions Main products Example HCN from KCN + H2SO4 in NaOH(aq) NaBH4 in NaOH r.t.p Hydroxynitrile CH3CHO + HCN CH3CH(OH)CN Primary alcohol CH3CHO + 2[H] CH3CH2OH 2,4-dinitrophenyl hydrazone (orange ppt) C6H3NO2NO2NH2 + CH3CHO ethanal 2-hydroxypropanenitrile Warm Reduction (aq) Additionelimination LiAlH4 in dry r.t.p. ether 2,4-dinitro r.t.p. phenylhydranine 2,4-dinitrophenylhydrazine C6H3NO2NO2NH-NCHCH3 + H2O 2,4-dinitrophenylhydrazone Oxidation M. Kole Tollen’s reagent, 2[Ag(NH3)2]+(aq) Fehling’s reagent Cu2+(aq)/ OH-(aq) r.t.p. Silver (mirror) CH3CHO +2[Ag(NH3)2]+ + 3OHCH3COO- + Ag + 4NH3 + 2H2O Warm Copper (I) oxide C2O (s) (brick-red ppt) CH3CHO + 2Cu2+ + 5OHCH3COO- + Cu2O + 3H2O 5 Triiodomethane test/iodoform test Oxidation Iodine in NaOH r.t.p. (aq) Triiodomethane, CHI3 (yellow ppt) CH3CHO + 3I2 + 4NaOH CHOO-Na+ + CHI3 + 3NaI + 3H2O triiodomethane Acidified K2Cr2O7 Warm Carboxylic acid CH3CHO + [O] reagents Conditions Main products Example HCN from NaCN + H2SO4 in NaOH (aq) r.t.p. Hydroxynitrile CH3COCH3 + HCN orange Cr2O7 CH3COOH 2- turns green Cr 3+ Ketones Type of reaction Nucleophilic addition propanone CH3C(OH)(CN)CH3 2-hydroxybutan-2-nitrile NaBH4 in NaOH Warm Reduction (aq) r.t.p. Additionelimination LiAlH4 in dry ether 2,4-dinitro phenylhydrazine Iodine in NaOH r.t.p. Triiodomethane test/iodoform test CH3COCH3 + 2[H] propan-2-ol Secondary alcohol r.t.p. (aq) 2,4-dinitrophenyl hydrazine (orange ppt) Triiodomethane, CHI3 (yellow ppt) CH3CH(OH)CH3 C6H3NO2NO2NH2 + CH3COCH3 C6H3NO2NO2NH-NC(OH)CH3 + H2O CH3CH2COCH3 + 3I2 + 4NaOH butanone CH3CH2COO-Na+ + CHI3 + 3NaI + 3H2O Reactions of organic nitrogen compounds Type of reaction Nucleophilic substitution (formation of nitrile from triiodomethane) Reduction reagents Conditions Main products Example KCN in alcohol reflux nitrile CH3I + CN - CH3CN ethanenitrile LiAlH4 in dry ether reflux Primary amine CH3CN + 4[H] CH3CH2NH2 Type of reaction Electrophilic substitution reagents Conditions Main products Example Bromine, Br2 (aq) r.t.p. Tribromophenylamine C6H5NH2 + 3Br2 (aq) Diazotization HNO2 from HCl + NaNO3 Below 5℃ ethylamine (formation of amine from nitrile) Phenylamine M. Kole Diazonium salt phenylamine + 3HBr (g) C6H5NH2 + HCl H2O C6H2Br3NH2 tribromophenylamine C6H5N2+Cl- + benzenediazonium chloride 6 Diazonium salt Type of reaction Hydrolysis Electrophilic substitutionelimination (coupling) reagents Conditions Main products Example Water, H2O Warm Phenol C6H5N2+Cl- + H2O Phenol in NaOH(aq) Below 5℃ (ice bath) reagents Conditions Main products Example Acyl chloride r.t.p. Amide CH3COCl + NH3 Azodye C6H5OH + N2 phenol + HCl C6H5N2+ + C6H5OH C6H5N=NC6H4OH + H+ 4-hydroxyphenylazobenzene (orange dye) Amine Type of reaction Nucleophilic substitutionelimination CH3CONH2 ethanoyl chloride ethanamide Amide Type of reaction Hydrolysis (of amides) Hydrolysis (of substituted amides) reagents Conditions Dilute acid/H2O Main products Example Carboxylic acid CH3CONH2 + H2O CH3COOH + ethanoic acid NH3 CH3CONH2 + NaOH CH3COO-Na+ sodium ethanoate + NH3 CH3CONHCH3 + H2O Boil Dilute alkali Acid salt Dilute acid/H2O Carboxylic acid and amine Boil methylethanamide CH3COOH + CH3NH2 methylamine Dilute alkali Acid salt and amine CH3CONHCH3 + NaOH CH3COO--Na+ + CH3NH2 Polymers Type of reaction Addition polymerisation Condensation polymerization (elimination) reagents Conditions Main products Example Monomers Heat, moderate pressure, catalyst Heat plymer n(CH2=CH2) Diamine + dioic acid in conc H2SO4 Diamine + acyl chloride Diol + dioic acid (CH2=CH2)n ethene monomers n(CH2=CHC6H5) phenylethene monomers Polyamide polythene polymer (CH2=CHC6H5)n polyphenylethene n[H2N(CH2)6NH2+ HOOC(CH2)COOH] 1,6-diaminohexane hexane-1,6-dioic acid [-HN(CH2)6NHOC(CH2)CO-]n nylon-6,6 r.t.p Polyamide Conc. H2SO4 Polyester n[H2N(CH2)6NH2 + ClOCCOCl] [-HN(CH2)6NHOC(CH2)CO-]n n[HO(CH2)2OH + HOOCC6H4COOH] ethanediol benzenedicarboxylic acid [-O(CH2)2OOCC6H4CO-]n terylene M. Kole
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