Compare the ease of carbon-carbon bond rotati | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(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 $C$.

Similar Questions

Shown below is the structure of methyl acetate with three different $\alpha, \beta$ and $\gamma$ carbon-oxygen bonds.
The correct order of bond lengths of these bonds is:

Identify the compound in which steric inhibition of resonance is present.

Which one among the following resonating structures is not correct?

Resonance effect is not observed in

Which of the following is not a valid resonating structure of the others?

Vedclass Test Series

Exam Paper Generator

Online Exam Module