Which of the following species has a positive | vedclass

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(C) In resonance,a positive charge must be in conjugation with a $\pi$-bond or a lone pair of electrons. $(A)$ Benzyl carbocation: The positive charge

Vedclass · Accepted Answer

Anilinium ion $(C_6H_5NH_3^{\oplus})$

Vedclass · Answer

(C) In resonance,a positive charge must be in conjugation with a $\pi$-bond or a lone pair of electrons. $(A)$ Benzyl carbocation: The positive charge on the carbon is in conjugation with the benzene ring,so it participates in resonance. $(B)$ $CH_2 = CH - CH = CH - CH_2^{\oplus}$: The positive charge is in conjugation with the $\pi$-bonds,so it participates in resonance. $(C)$ Anilinium ion $(C_6H_5NH_3^{\oplus})$: The positive charge is on the nitrogen atom,which has no vacant $p$-orbital or lone pair to participate in resonance with the benzene ring. The nitrogen is $sp^3$ hybridized and cannot extend conjugation. Thus,the positive charge is not involved in resonance. $(D)$ Tropylium cation: The positive charge is part of a cyclic conjugated system,so it participates in resonance. Therefore,the correct option is $C$.

Which of the following species has a positive charge that is not involved in resonance?

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