Organic 2 Review Problem 390

Organic 2 Review Problem 390 - 374 PRACTICAL O RGANIC...

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374 PRACTICAL ORGANIC CHEMISTRY gently for 15 minutes. Pour into water: the solid anilide separates. Filter off, wash with water, and recrystallise from water or dilute methylated spirit. Note the m.p. (, pp. 550-551.) 3. (a) Benzoylation (p. 243). Mix together in a strong boiling-tube i ml. (or i g.) of the substance and 20 ml. of io% NaOH solution. Add 1-1-5 ml. of benzoyl chloride (0-5 ml. at a time) until shaking the mixture vigorously in the securely corked boiling-tube gives no further separation of the semi-solid benzoyl derivative. Then continue the shaking for 5 minutes, and finally filter off the solid, wash well with water, and recrystallise from methylated spirit. Take the m.p. (, pp. 550-55 1 O ( b ) Toluene-p-sulphonylation (p. 247). Proceed as in 3(0), but using 1-5 g. of toluene- p -sulphonyl chloride, either finely powdered or in concentrated acetone solution. Note. The sulphonyl derivative of a primary amine is soluble in aqueous sodium hydroxide, and the final
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