H NMR (60 MHz, CDCl3) delta 3.05, 6H, s; delta 6.69, 2H, d; delta 7.71, 2H, d; d
ID: 861959 • Letter: H
Question
H NMR (60 MHz, CDCl3) delta 3.05, 6H, s; delta 6.69, 2H, d; delta 7.71, 2H, d; delta 9.70, 1H, s. A brown liquid (I) boiled at 193-195 degree C. It contained nitrogen but gave negative tests for sulfur and the halogens. It was insoluble in water but soluble in dilute acid. It did not react with acetyl chloride or benzenesulfonyl chloride. Treatment of a hydrochloric acid solution of the unknown compound with sodium nitrite, followed by neutralization, gave a compound (II) that melted at 164 degree C. Compound II was insoluble in alkalies but dissolved in boiling concentrated sodium hydroxide solution, with the liberation of a gas (III). This gas (III) was absorbed in water, and the aqueous solution was treated with phenyl isothiocyanate to form a compound (IV) with a melting point of 134-135 degree C. Careful acidification of the alkaline solution, followed by extraction, gave a compound (V) that melted at 125-126 degree C. The 1H NMR spectrum of compound V (60 MHz, acetone) showed delta 6.63, 2H, d; delta 7.67, 2H, d; delta 8.7, 1H, bs. The delta 8.7 signal was so broad as to be detectable only by electronic integration. A colorless liquid was found to be soluble in water and in ether. It boiled at 94 - 96 degree C, and gave negative tests for the halogens, nitrogen, and sulfur. It a dilute potassium permanganate solution, decolorized bromine inExplanation / Answer
The color less liquid is propanol. its boiling point is 96 o C. When it mix with dilue potassium permanganate solution it get oxidized to propanal and propanoic acid, and decolorizes potassium permanganate .
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