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.) 

🤓 Based on our data, we think this question is relevant for Professor Bertrand's class at UCSD.

FREE Expert Solution
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.) 

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Solvents concept. You can view video lessons to learn Solvents. Or if you need more Solvents practice, you can also practice Solvents practice problems.

What is the difficulty of this problem?

Our tutors rated the difficulty ofDimethylformamide (DMF), HCON(CH3)2, is an example of a pola...as medium difficulty.

How long does this problem take to solve?

Our expert Organic tutor, Jonathan took undefined 56 seconds to solve this problem. You can follow their steps in the video explanation above.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Bertrand's class at UCSD.

What textbook is this problem found in?

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.