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Organic Lab Reactions 232

Organic Lab Reactions 232 - example given 3-nitrobiphenyl...

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MECHANISMS OF THE REACTIONS 227 1. Acetylation of the amine. 2. Nitrosation of the acetylamine by means of N 2 O 3 * or N0C1. —COCH 3 + N 2 O 3 NO 2 H N—COCH3 + N0C1 + CHjCOjjNa NO N—COCHs + H 2 O or, NO 2 NO 2 3. Reaction of the nitrosoacetylamine with a liquid aromatic com- pound. NO N—COCH3 + NaCl + CH3CO2H N—COCH3 + N 2 + CH 3 CO 2 H NOJS NO 2 The nitrosation is carried out by passing nitrous fumes into an ice- cold solution or suspension of the acetylamine in acetic acid and acetic anhydride, or by adding a solution of nitrosyl chloride to the acetylamine and sodium acetate in acetic acid. The nitroso derivative is precipitated by pouring the solution into ice water and is extracted by the aromatic liquid or filtered and added to the liquid with which it reacts. In the
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Unformatted text preview: example given, 3-nitrobiphenyl is obtained from ra-nitroacetanilide in 63% yield. MECHANISMS OF THE REACTIONS When a dilute solution of sodium hydroxide is added gradually to a solution of an aryldiazonium salt, such as diazotized p-bromoaniline or p-nitroaniline, a yellow solid is precipitated. The same yellow solid can be obtained by adding an acid to the sodium diazotates, RNaONa, formed by addition of the diazonium salt to an excess of sodium hydrox-ide. These products, which are exceedingly unstable and explosive in the * So-called nitrous fumes, a mixture of NO and NO2 actually is used in the reaction...
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