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From the video we see that the ammonia and butylamine react quite vigorously with the ethanoyl chloride. The ethyl 4-aminobenzoate is noticeably less reactive. There are a couple of possible explanations for this. First, being a solid we might expect that reaction would be slower as it cannot mix so well with the other reactant. Second, we saw that the arylamine was a weaker base because the lone pair of electrons on the nitrogen atom was partly delocalised in the benzene ring. For the same reason the lower electron density on the nitrogen atom makes the molecule less good as a nucleophile.
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The white fumes seen in the first experiment are ammonium chloride formed by the reaction between the ammonia and the hydrogen chloride gas given off by the experiment:
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The reaction between ammonia and ethanoyl chloride produces the white solid, ethanamide:
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CH3COCl(l) + NH3(aq) ⇒ CH3CONH2(aq) + HCl(g) |
With butylamine an N-substituted amide is produced called N-butyl ethanamide:
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CH3COCl(l) + C4H9NH2(l) ⇒ CH3CONHC4H9 + HCl(g) |
