Hydroxylamine Test for Nitriles

Hydroxylamine and its hydrochioride may have mutagenic effects. Wear latex gioves when handiing them. Shouid either of these substances contact your skin, immediateiy fiood the affected area with water. 

Preparation Sign in at www.cengage.com/login to read the MSDSs for the chemi-cais used or produced in this procedure. 

In a large test tube, prepare a mixture consisting of 2 ml of 1 M hydroxylamine hydrochloride in propylene glycol, 30-50 mg of the compound that has been dissolved in a minimum amount of propylene glycol, and 1 ml of 1 A/f potassium hydroxide. Heat the mixture to boiling for 2 min and then cool it to room temperature. Add 0.5-1.0 ml of a 0.5 M alcoholic ferric chloride solution. A red-to-violet color is a positive test. Yellow colors are negative, and brown colors and precipitates are neither positive nor negative. 

On hydrolysis in either acidic or basic solution, nitriles are ultimately converted to the corresponding carboxylic acids (Eqs. 25.66 and 25.67). It is then possible to prepare a derivative of the acid using methods provided in Section 25.13. 

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