Question

Reaction of iodoethane with CN $^{-}$ yields a small amount of isonitrile, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N} \equiv \mathrm{C},$ along with the nitrile $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{N}$ as the major prod- uct. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.

          Reaction of iodoethane with CN $^{-}$ yields a small amount of isonitrile, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N} \equiv \mathrm{C},$ along with the nitrile $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{N}$ as the major prod-
uct. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.

Added by Jeffery H.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

07/06/2022

Step 1

Step 2: The electron-dot structure for the nitrile, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{N}$ can be drawn as follows: \[ \mathrm{H} \quad \mathrm{H} \quad \mathrm{H} \quad \mathrm{C} \quad =\mathrm{N} \] The carbon atom has a formal charge of 0, Show more…

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Reaction of iodoethane with CN $^{-}$ yields a small amount of isonitrile, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N} \equiv \mathrm{C},$ along with the nitrile $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{N}$ as the major prod- uct. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.