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Why Glycine exist as $(H_3N+CH_2COO^−)$ while antranilic acid ($p − NH_2 − C_6H_4 − COOH)$ does not exist as dipolar ion ?

$\begin{array}{1 1}(a)\;-COOH\text{ is too weakly acidic to transfer }H^+\text{ to the weakly basic } −NH_2\text{ attached to the electron withdrawing benzene ring}\\(b)\;-COOH\text{ is too strong acidic to transfer }H^+\text{ to the weakly basic } −NH_2\text{ attached to the electron withdrawing benzene ring}\\(c)\;-COOH\text{ is too weakly acidic to transfer }H^+\text{ to the strong basic } −NH_2\text{ attached to the electron withdrawing benzene ring}\\(d)\;-COOH\text{ is too weakly acidic to transfer }H^+\text{ to the weakly basic } −NH_2\text{ attached to the electron donating benzene ring}\end{array} $

1 Answer

-COOH is too weakly acidic to transfer $H^+$ to the weakly basic $−NH_2$ attached to the electron withdrawing benzene ring.When attached to aliphatic car- bon , the $NH_2$ is sufficiently basic to accept $H^+$ form -COOH group.
Hence (a) is the correct answer.
answered Mar 26, 2014 by sreemathi.v
 
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