chem262lexp8 - AtLee Watson Experiment 8 Electrophilic...

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AtLee Watson Experiment 8: Electrophilic Aromatic Substitution: Nitration of 4-methylacetanilide After the nitration of 4-methylacetanilide, the product was recrystallized and then its purity was determined from a melting point determination and thin-layer chromatography (TLC). The percent yield of the 2-nitro-4-methylacetanilide was calculated to be 115%. The percent yield exceeding 100% was caused by excess water and impurities in the product. The melting point was determined to be 87.5 0 C-88.5 0 C, while the accepted value is 96 0 C. Upon analysis by TLC the R f values of the crude, purified, and the starting material 4-methylacetanilide were measured to be 0.85, 0.90, and 0.64 respectively. 1. 2. If 10:1 ratio of hexanes:ethanol were used, the eluent solvent would be much less polar. This would cause the purified and crude product of 2-nitro-4-methylacetanilide to not move because they are more polar than the solvent and it would not be displaced and travel along the plate, thus giving no separation. This would give an R f
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