Dimethylformamide (DMF), HCON(CH3)2, is an example of a polar aprotic solvent, aprotic
Chapter 3, Problem 3.43(choose chapter or problem)
Dimethylformamide (DMF), HCON(CH3)2, is an example of a polar aprotic solvent, aprotic meaning it has no hydrogen atoms attached to highly electronegative atoms. (a) Draw its dash structural formula, showing unshared electron pairs. (b) Draw what you predict to be its most important resonance forms [one is your answer to part (a)]. (c) DMF, when used as the reaction solvent, greatly enhances the reactivity of nucleophiles (e.g., - CN from sodium cyanide) in reactions like this: NaCN + CH3CH2Br 9: CH3CH2C iw N + NaBr Suggest an explanation for this effect of DMF on the basis of Lewis acidbase considerations. (Hint: Although water or an alcohol solvates both cations and anions, DMF is only effective in solvating cations.)
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