Can the benzene ring attached to aniline be detached in an aqueous solution (specifically groundwater) under certain conditions? Would the two compounds be detected as separate entities in a laboratory analysis?
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$\begingroup$ You can turn aniline back into benzene but that requires a few steps and usually loses the amino group altogether. Since benzene and aniline are two separate compounds, what makes you think that they would not be detected separately? $\endgroup$– JanOct 20, 2015 at 20:13
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2$\begingroup$ In aniline there's no benzene, but phenyl group and amino group, which can't be simply separated. $\endgroup$– MithoronOct 20, 2015 at 20:43
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$\begingroup$ Simplest way to convert aniline to benzene is $\ce{NaNO2}/\ce{HCl}$ followed by $\ce{H3PO2}$ en.wikipedia.org/wiki/Diazonium_compound $\endgroup$– orthocresolOct 20, 2015 at 22:31
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Aniline is not easily converted to benzene in aqueous conditions. A google search turns up several papers describing the breakdown products of aniline in groundwater but benzene is not one of them. Methanogenic and denitrifying bacteria seem to play a key part in aniline breakdown, releasing methane and carbon dioxide as byproducts. The other main products seem to be polymerisation products resulting from condensation and oxidation reactions.
In answer to your question about detection; no you would not expect to see benzene as a breakdown product in a sample of groundwater that has been contaminated by aniline.