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Propionitrile()is deprotonated by very strong bases. Write resonance forms to show the stabilization of the carbanion that results.

Short Answer

Expert verified

Effect of a strong base

Strong bases abstract protons from the alpha carbon attached to the electron-withdrawing group.

Step by step solution

01

Step 1:

Effect of a strong base

Strong bases abstract protons from the alpha carbon attached to the electron-withdrawing group.

02

Step 2:

Proton abstraction by strong base in propionitrile

Here in propionitrile, the nitrile group is a strong electron-withdrawing group, and base abstract proton from the adjacent carbon results in the formation of carbanion. The carbanion formed is stabilized by the nitrile group as the negative charge moves from carbon to nitrogen of the nitrile group (shown above). In conclusion, we say that the resulting carbanion is stabilized by resonance.

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