Organic 2 Review Problem 314

Organic 2 Review Problem 314 - 298 PRACTICAL ORGANIC...

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298 PRACTICAL ORGANIC CHEMISTRY When the crude reaction product is made alkaline and steam-distilled, a mixture of quinoline and some unchanged aniline passes over. Pure quinoline can be isolated from this mixture by one of the following methods: (1) The mixed bases are dissolved in dilute hydrochloric acid and sodium nitrite solution added. The aniline is thus diazotised and, if the mixture is subsequently boiled, converted into phenol. The solution is then made alka- line and steam-distilled, the quinoline passing over, while the phenol remains behind in the alkaline solution. (2) The mixed bases are boiled with an acetic acid-acetic anhydride mixture to convert the aniline into acetanilide. The product is poured into water, when the acetanilide crystallises out while the quinoline remains in solution as quinoline acetate. The acetanilide is filtered off, and the filtrate made alkaline and steam-distilled. (3) The mixed amines are dissolved in hydrochloric acid and zinc chloride
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