If a quarternary ammonium ion can undergo an elimination reaction with a strong

Question

If a quarternary ammonium ion can undergo an elimination reaction with a strong base, why can't a protonated tertiary amine undergo the same reaction?If a quarternary ammonium ion can undergo an elimination reaction with a strong base, why can't a protonated tertiary amine undergo the same reaction?

A) because required for E2 elimination anti-conformation of a protonated tertiary amine is destabilized by close interaction of two positive charges B) because the nitrogen atom of a protonated tertiary amine is more sterically hindered than the nitrogen atom of a quaternary ammonium salt. C) because there is no hydrogen at the -carbon in the protonated tertiary amine and therefore there is nothing to remove D) because the strong base will immediately remove a proton from the protonated amine, and then the leaving group would be a strong basic amide ion, which is too strong a base to be able to leave.

Explanation / Answer

D) because the strong base will immediately remove a proton from the protonated amine, and then the leaving group would be a strong basic amide ion, which is too strong a base to be able to leave.

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