Which of the following is the least stable resonating structure:

C H_{2} = C H - \oplus C H - ⊖ C H - O C H_{2} - C H_{2} - C H_{3}

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⊖ C H_{2} - \oplus C H - C H = C H - O C H_{2} - C H_{2} - C H_{3}

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⊖ C H_{2} - C H = C H - C H = \oplus O C H_{2} - C H_{2} - C H_{3}

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C H_{2} = C H - ⊖ C H - C H = \oplus O C H_{2} - C H_{2} - C H_{3}

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Solution

The correct option is B $⊖ C H_{2} - C H = C H - C H = \oplus O C H_{2} - C H_{2} - C H_{3}$
If all structures have formal charge, the most stable one is that in which the negative and positive charges reside on the most electronegative and the most electropositive atoms respectively. Both these points are disfavored by the resonance structure of option C.

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A g N O_{3}

I . ⊖ C H_{2} - \oplus C H - C H = C H - O - C H_{3}

I I . ⊖ C H_{2} - C H = C H - \oplus C H - O - C H_{3}

I I I . C H_{2} = C H - ⊖ C H - \oplus C H - O - C H_{3}

I V . C H_{2} = C H - ⊖ C H - C H = \oplus O - C H_{3}

C H_{2} = C H - C H = C H - O - C H_{3}

A . C H_{3} - C H = C H_{2} + H C l ⟶ C H_{3} - C | C l H - C H_{3}

B . C H_{3} - C H = C H_{2} + H B r ⟶ C H_{3} - C H_{2} - C H_{2} B r

C . C H_{3} - C H = C H_{2} + H B r p e r o x i d e - ---- \to C H_{3} - C H_{2} - C H_{2} - B r

D . C H_{3} - C H = C H_{2} + H I p e r o x i d e - ---- \to C H_{3} - C | I H - C H_{3}

C H_{3} - C H_{3}, C H_{2} = C H_{2}

C H \equiv C H

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