# 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. (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 → CH3CH2C≡N + NaBr Suggest an explanation for this effect of DMF on the basis of Lewis acid–base considerations. (Hint: Although water or an alcohol solvates both cations and anions, DMF is only effective in solvating cations.)

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###### Problem Details

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.

(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 → CH3CH2C≡N + NaBr

Suggest an explanation for this effect of DMF on the basis of Lewis acid–base considerations. (Hint: Although water or an alcohol solvates both cations and anions, DMF is only effective in solvating cations.)

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Solomons 10th Edition. You can also practice Organic Chemistry - Solomons 10th Edition practice problems.