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Toluene, Methyl Benzene Or Phenyl Methane

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Toluene, Methyl Benzene Or Phenyl Methane Toluene, methyl benzene or phenyl methane. Toluene is the simplest homolouge of benzene. It was first obtained by dry distillation of tolubalsam and hence named toluene. It is commercially known as tolual. (1) Methods of preparation CH3 (i) From benzene [Friedel-craft's reaction] : + AlCl3 CH3Cl + HCl Benzene Toluene Note: Alkyl halide employed may undergo an isomeric change CH AlCl3 3 C6 H 6 ClCH 2CH 2CH 3 C6 H 5 CH HCl n Propyl chloride CH 3 Isopropyl benzene (65 70%) Catalysts can be used in place of anhydrous AlCl 3 are, AlCl 3 SbCl 3 SnCl 4 BF3 ZnCl 2 HgCl 2 Ether Br + 2Na + BrCH3 CH3 + 2NaBr (ii) Wurtz fitting reaction: Bromobenzene Methyl bromide Toluene CH 3 Soda lime (iii) Decarboxylation: C6 H 4 NaOH C6 H 5 CH 3 Na 2 CO 3 COONa Toluene (o-,m- or p-) Sodium toluate CH3 CH3 OH (iv) Fromcresol: heat + Zn + ZnO o-Cresol Toluene CH3 CH3 (v) From toluene sulphonic acid: + HOH + H2SO4 SO3H Toluene p-Toluene sulphonic acid CH3 CH3 CH3 NaNO2 C2H5OH + N2 + CH3CHO + HCl HCl NH2 N2Cl Toluene p-Toluidine p-Toluene diazonium chloride (vi) Fromtoluidine: MgBr CH3 (vii) From grignardreagent: + CH3Br + MgBr2 Phenyl magnesium bromide Toluene (viii) Commercial preparation From coal tar: The main source of commercial production of toluene is the light oil fraction of coal-tar. The light oil fraction is washed with conc. H 2 SO 4 to remove the bases, then with NaOH to remove acidic substances and finally with water. It is subjected to fractional distillation. The vapours collected between 80 110 C is 90% benzol which contains 70 80% benzene and 14 24% toluene. 90% benzol is again distilled and the portionCH3 distilling between 108 110 C is collected. It is toluene. | (ix) From n- heptane and methyl cyclohexane CH3 H C CH 2 3 Cr2O3 / Al2O3 500-550°C H2C CH2 Toluene CH2 n-Heptane (2) Physical properties (i) It is a colourless mobile liquid having characteristic aromatic odour. (ii) It is lighter than water (sp. gr. 0.867 at 20°C). (iii) It is insoluble in water but miscible with alcohol and ether in all proportions. (iv) Its vapours are inflammable. It boils at 110°C and freezes at –96°C. (v) It is a good solvent for many organic compounds. (vi) It is a weak polar compound having dipole moment 0.4D. (3) Chemical properties:Toluene shows the behavior of both CH3 Side chain (Aliphatic) Benzene ring (Aromatic) (i) Electrophilic substitution reactions: Aromatic character (More reactive than benzene) due to electron releasing nature of methylCH 3group. CH3 CH3 E + E + Electrophile o-Derivative E + p-Derivative Note: E may be chlorine, HNO 3 , H 2SO 4 ,CH 3Cl . (ii) Reactions of side chain CH3 CH2Cl CHCl2 CCl3 Cl2 Cl2 Cl2 (a) Side chain halogenation : UV UV UV Toluene Benzyl chloride Benzal chloride Benzo trichloride Note: Benzyl chloride on hydrolysis with aqueous caustic soda forms benzyl alcohol. C6 H5CH 2Cl NaOH C6 H5CH 2OH NaCl (Phenyl methyl chloride) Benzal chloride on hydrolysis forms benzaldehyde. C6 H 5 CHCl 2 2NaOH C 6 H 5 CH (OH )2 2NaCl (Benzylide chloride) C6 H5CHO H 2O Benzotrichloride on hydrolysis forms benzoic acid. C6 H5CCl 3 3NaOH C6 H5C(OH)3 3NaCl (Benzylidyne chloride) C6 H5COOH H 2O (b) Oxidation: CH3 COOH + KMnO4 / H With hot acidic KMnO : + H2O 4 3[O] CHO Toluene Benzoic acid CH3 CrO2C2 + 2[O] + H2O With acidic manganese or chromyl chloride (Etards reaction) : Toluene Benzaldehyde Note:All alkyl benzenes on oxidation with hot acidic KMnO 4 or Na 2Cr2O7 form benzoic acid. The length of the side chain does not matter. R R (c) Hydrogenation: + 3H2 Na Birch/ liquid reduction NH 3 – Alkyl benzene Alkyl cyclohexane CH3 CH3 | | HC CH H2C CH2 3H + 2 Ni200°C HC CH H2C CH2 CH CH2 Methyl benzene Methylcyclohexane (d) Combustion: C6 H 5CH 3 9O2 7CO 2 4 H 2O (e) Ozonolysis: O O H O CH HC CH O C C CH Zn CH–C=O CHO +3O3 O +2 + 3H2O2 CH HOH HC CH C O H – C=O CHO O C Methyl glyoxal Glyoxal C H O O Toluene Triozonide (4) Uses (i) In the manufacture of benzyl chloride, benzal chloride, benzyl alcohol, benzaldehyde, benzoic acid, saccharin, etc. (ii) In the manufacture of trinitrotoluene (TNT), a highly explosive substance. (iii) As an industrial solvent and in dry-cleaning. (iv) As a petrol substitute. (v) In the manufacture of certain dyes and drugs. T.N.T. (Tri-nitro toluene) CH3 CH3 Preparation : O2N NO2 + 3HNO3 H2SO4 + 3H2O Fuming Toluene NO 2 Properties : It is pale yellow crystalline solid (M.P. = 81°C). Uses : It is used as an explosive in shells, bombs and torpedoes under the name trotyl. When mixed with 80% ammonium nitrate it forms the explosive amatol. TNT is also used as a mixture of aluminium nitrate, alumina and charcoal under the name ammonal. T.N.B. (Tri-nitro benzene) CH3 CH3 COOH O2 NO O2 NO O2 NO K2Cr2O7 Soda HHNO2SO3 4 Preparation : H2SO4 lime Toluene NO NO NO T.N.B. Properties and uses: It is colorless solid (M.P. = 122°C). It is more explosive than T.N.T. and used for making explosive. .
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