Lab 6: Electrophilic Aromatic Substitution

Lab 6: Electrophilic Aromatic Substitution(1) Nitration of methyl group Benzoate(2) Synthesis of 1,4-Di-t-butyl-2,5-dimethoxybenzene byFriedel-Crafts Alkylation of 1,4-DimethoxybenzenePurpose1)To carry shade forward the nitration of methyl benzoate, and indeed identify the major intersection organize (position at which nitro-group substitute takes place) by thin-layer chromatography (TLC), the portion refund and the liquescent point range. 2)To synthesize 1,4-Di-t-butyl-2,5-dimethoxybenzene by Friedel-Crafts Alkylation of 1,4-Dimethoxybenzene, and then bump the percent yield and dissolve point range. Procedure* beguile mend to the lab sack 6 and Macroscale and Microscale Organic Experiments (Williamson, 2003). * vary II of the experiment (Synthesis of 1,4-Di-t-butyl-2,5-dimethoxybenzene by Friedel-Crafts Alkylation of 1,4-Dimethoxybenzene) was carried proscribed by Ashley and me. mapping I (nitration of methyl benzoate) was carried out by Jenny. Physical mensuration TableType of substanceMolecular FormulaMolecular incubus (g/mol)Density(g/cm3)M.P.(oC)B.P.(oC)Methyl benzoateC8H8O2136.161.094-15198-200Methyl 2-nitrobenzoateC8H7NO4181.141.289-13104Methyl 3-nitrobenzoateC8H7NO4181.14-78-80289Methyl 3,5-dinitrobenzoateC8H6N2O6226.14544-106-109-Methyl 4-nitrobenzoateC8H7NO4181.15-94-96-1,4-DimethoxybenzeneC8H10O2138.161.0555-582131,4-Di-t-butyl-2,5-dimethoxybenzeneC16H26O2250.37-104-105-2-methyl-2-propanolC4H10O74.12-25.482.4Hazard Concentrated sulfuric battery- sultry and nitric acerb ar highly corrosive. ObservationPart II Friedel-Crafts AlkylationThe concentrated sulfuric erosive utilize was yellow. 1,4-Dimethoxybenzene was in flannel crystal degree. The t-butyl alcohol coagulate in room temperature, so it took a while to conflagrate it up and return to liquifiable form. After concentrated sulfuric acid was added to the t-butyl alcohol, acetic acid and 1,4-Dimethoxybenzene mixture, the solution became light cook in color. After heating system for a while, white precipitous could be observed at the bottom of the tube.

After urine was added, the white precipitate fade away and the solution turned milky. The crystals obtained afterward recrystallization be in form of large slides. They are grinded into fine-grained or smaller granules for melt point test. DataPart IMass of methyl benzoate = 0.30gMass of recrystallized crop = 0.28436gMelting get Range of nitration overlap = 75 oC - 83 oCChemical CompoundsDistance from B to spot (cm)Distance from B to SF(cm)Distance from B to spots (cm)/Distance from B to SF (cm)Retention FactorRfMethyl benzoate1.684.501.68/4.500.37(ortho) Methyl 2-nitrobenzoate1.304.521.30/4.520.29(meta) Methyl 3-nitrobenzoate1.804.501.80/4.500.40Methyl 3,5-dinitrobenzoate1.304.401.30/4.400.30(para)Methyl 4-nitrobenzoate1.804.301.80/4.300.42Unknown Product1.804.301.80/4.300.42Table one... If you call for to get a broad essay, aver it on our website: Orderessay

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