The most likely protonation site in the follo | vedclass

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Question

(A) The molecule is $8,8-dimethylheptafulvene$. Protonation at the $C-1$ position (the exocyclic double bond) leads to the formation of a $tropylium$

Vedclass · Accepted Answer

$C-1$

Vedclass · Answer

(A) The molecule is $8,8-dimethylheptafulvene$. Protonation at the $C-1$ position (the exocyclic double bond) leads to the formation of a $tropylium$ cation, which is a stable aromatic species ($6\pi$ electrons, $H$ückel's rule). Since the resulting carbocation is aromatic and highly stable, the $C-1$ position is the most reactive site towards protonation. Protonation at any other position on the seven-membered ring would disrupt the conjugation or fail to produce an aromatic system, making those sites less favorable.

The most likely protonation site in the following molecule is:

Similar Questions

Which of the following statements is $NOT$ correct for heterolysis?

Which different types of reaction mechanisms are observed in addition reactions?

The order of decreasing reactivity in electrophilic addition of the following compounds is
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