Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2021/paper-1/2/b/iii/solution

Acetonitrile is suitable: it dissolves the organic reagents, is polar enough to stabilize the developing ionic products and is an aprotic, relatively unreactive medium. It does not strongly hydrogen-bond-solvate the amine lone pair or compete efficiently as the methylating nucleophile. Sufficient solubility and chemical compatibility matter as well as polarity.

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