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NITRO DERIVATIVES OF TOLUENE 309

strongly reinforced by the induction effect of three nitro groups. This is why trinitro-

toluene readily reacts with p- nitrosodimethylaniline in the presence of hydroxides

to form an anil (XV), which then hydrolyses to trinitrobenzaldehyde:

(13)

Trinitrotoluene reacts in a similar way with benzaldehyde in an alkaline medium

to form a stilbene derivative:

(14)

The reaction is strongly exothermic. For example, a mixture of trinitrotoluene and

benzaldehyde, in the absence of a solvent, reacts when a few drops of piperidine

are added. The reaction is so violent that the mixture may ignite. The methyl group

of trinitrotoluene reacts with other aldehydes in a similar way. For this reason

trinitrotoluene should be protected against the action of aldehydes, especially in
alkaline media. Aldehydes may be formed under the influence of acids on wood.

Hence, wooden vats which were formerly used for washing TNT are hardly used.
now.