From 2 methyl pentan -2-ol sodium hydroxide
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A. 2-Hydroxybutanenitrile. A 3-L, three-necked, round-bottomed flask is fitted with a mechanical stirrer and thermometer and charged with 312 g (3.0 mol) of sodium bisulfite and 1050 mL of water. The stirrer is started and after the sodium bisulfite has dissolved, the flask is placed in an ice–salt bath. A solution of 147 g (3.0 mol) of sodium cyanide (Note 1) in 450 mL of water and 174 g (3.0 mol) of propanal (Note 2) are separately cooled to 0°C in ice–salt baths. When the temperature of the vigorously stirring sodium bisulfite solution has stabilized at 0°C the cold propanal is added in one portion. The temperature of the reaction solution immediately increases to ca. 35°C and then returns to ca. 0°C. After 30 min the cold sodium cyanide solution is added in one portion. The reaction mixture again warms to ca. 15°C and then returns to ca. 0°C. This mixture is stirred for 2 hr at 0°C, during which time a thick white precipitate of sodium sulfite forms. The supernatant liquid is decanted into a 4-L separatory funnel and the precipitate is washed with 1 L of ice–water. The combined aqueous solution is extracted with three 1-L portions of ethyl ether. The combined ether extracts are washed with 1 L of saturated brine and dried by stirring (magnetic stirring bar) over magnesium sulfate for 2 hr. The solution is filtered through a coarse, sintered-glass funnel and the ether is removed with a rotary evaporator at water aspirator pressure. After the pH of the residue is adjusted to 5 with a few drops of concentrated hydrochloric acid (Note 3), the residue is distilled to give 154–192 g (60–75%) of 2-hydroxybutanenitrile, bp 108–114°C (30 mm), as a colorless liquid (Note 4).
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