Bromide ion → 4-Pentenenitrile

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A flask was equipped with stirrer, reflux condenser, thermometer, and charged with 75 ml of water and 36.8 grams (0.75 mole) sodium cyanide. Stirring was commenced and there was added 8.5 grams of tricapryl(methyl)ammonium chloride (ALIQUAT 336 phase-transfer catalyst) followed by 67.5 grams (0.50 mole) of the bromide product mixture comprising 55.7% cyclopropylmethyl bromide, 37.2% bromocyclobutane, and 7.1% bromobutene. The mixture slowly exothermed to about 50° C. After about 1 hour, heating was commenced so as to maintain the temperature of the mixture at 45° C. After 7 hours, gas chromatographic analysis of the organic phase indicated that cyclopropylmethyl bromide and 4-bromo-1-butene (i.e., bromobutene) were consumed, that cyclobutyl bromide was unchanged, and that cyclopropylacetonitrile and 1-cyano-3-butene were formed. The ratio (area %) of cyclopropylacetonitrile to 1-cyano-3-butene was 88:12. A minute trace (less than 1 area %) of cyanocyclobutane was detected.

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