REACTIONS AND IDENTIFICATION 361 (B) RCONH 2 + NaOH = RCOONa + NH 3 CO /COOXa (C) R< >NH + 2NaOH = R< + NH 3 ^CO COONa (D) RCN + NaOH + H 2 O = RCOOXa + NH 3 Place together in a 50 ml. conical flask about i g. of the substance and io ml. of 10% NaOH solution (or use apparatus in Fig. 38, p. 63). Add a few pieces of unglazed porcelain, fit a reflux water-condenser, and boil gently for about 20 minutes. Nitriles require longer heating than amides, usually about 30 minutes. The completion of the hydrolysis of an insoluble nitrile (e.g., benzonitrile) is indicated by the disappearance of oily drops in the liquid. Cool the flask, add an excess of dil. H 2 SO 4 and cool thoroughly. (a) A white precipitate indicates an aromatic acid: filter ofT, wash well with water and (i) carry out tests for benzoic, salicylic and phthalic acids (Section 14, p. 347), or (ii), recrystallise from water and take m.p. Phthalic acid is moderately soluble in cold water, and is therefore precipitated only if the volume of the liquid is kept
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