Determine the order of bond length for the C- | vedclass

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(A) In structure $x$ (cyclohexylamine),the $C-N$ bond is a pure single bond because there is no resonance. In structure $z$ (aniline),the lone pair on

Vedclass · Accepted Answer

$x > z > y$

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(A) In structure $x$ (cyclohexylamine),the $C-N$ bond is a pure single bond because there is no resonance. In structure $z$ (aniline),the lone pair on the nitrogen atom is in conjugation with the benzene ring,which imparts partial double bond character to the $C-N$ bond,thereby shortening it. In structure $y$ ($p$-nitroaniline),the $-NO_2$ group is a strong electron-withdrawing group that increases the extent of resonance between the $-NH_2$ group and the benzene ring. This results in a greater partial double bond character in the $C-N$ bond compared to aniline $(z)$. Therefore,the bond length order is $x$ (single bond) $>$ $z$ (partial double bond) $>$ $y$ (greater partial double bond character). The correct order is $x > z > y$.

Determine the order of bond length for the $C-N$ bonds labeled as $x$,$y$,and $z$ in the given structures.

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