Amines are less reactive in substitution reactions. Their reactivity is much lesser than alcohols and alkylflourides towards substitution. Protonation of the amino group makes it a better leaving group, but not nearly as good a leaving group as a protonated alcohol. Protonated amino groups cannot be displaced by `OH^(-)` because it would react immediately with the acidic hydrogen which would convert it in to a poor nucleophile. The leaving group in quarternary ammonium ion has about the same leaving tendency as a protonated amino group but does not have acidic hydrogen. the reaction of a quarternary ammonium ion with hydroxide ion is known as Hoffmann elimination reaction. The leaving group is tertiary amine. Since a tertiary amine is only a moderately good leaving group, the reaction requires heat. The carbon to hwich the tertiary amine is attached is designated as `alpha` carbon. When the hydroxide ion starts to remove a `beta` H form from a quarternary ammonium ion, the leaving group does not immediately start to leave because a tertiary amine is not a good leaving group. As a result, a partial negative charge bulds up on the carbon from which the proton is removed.
Which of the following statements is correct?
A. `PK_(a)` value of protonated amine is more than that of protonated alcohol
B. `PK_(a)` valued of the protoned amine is less than that of protonated alcohol
C. `PK_(a)` value of protonated amine is equals to that of protonated alcohol
D. `PK_(a)` value of amine is less than that of alcohol

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1 Answers

Correct Answer - A
Based on relative strengths of amines and alcohols

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