Compare the ease of carbon-carbon bond rotati | vedclass

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(C) The ease of rotation about the carbon-carbon bond depends on the extent of double bond character. The double bond character is determined by the s

Vedclass · Accepted Answer

$B > A > C$

Vedclass · Answer

(C) The ease of rotation about the carbon-carbon bond depends on the extent of double bond character. The double bond character is determined by the stability of the zwitterionic resonance structure formed by charge separation.$1$. In structure $B$,charge separation leads to two aromatic rings (cyclopropenyl cation and cyclopentadienyl anion),which is highly stable.$2$. In structure $A$,charge separation leads to one aromatic ring (cyclopropenyl cation) and one non-aromatic ring.$3$. In structure $C$,charge separation leads to one aromatic ring and one anti-aromatic ring (cyclopropenyl anion),which is highly unstable.Since the stability of the zwitterionic form is $B > A > C$,the extent of double bond character (and thus the energy barrier for rotation) follows the order $C > A > B$. Therefore,the ease of rotation is $B > A > C$.

Compare the ease of carbon-carbon bond rotation across $A, B,$ and $C$.

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