See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

Step 1 - Identify the substrate: The starting material is 7-bromocyclohepta-1,3,5-triene (tropylium bromide precursor). It has a seven-membered ring with three double bonds and a sp3 CH-Br at C7. Step 2 - Reaction with AgNO3: AgNO3 abstracts the bromide ion (forming AgBr precipitate), generating the tropylium cation (cycloheptatrienyl cation, C7H7+). This is a classic ionization driven by exceptional carbocation stability. Step 3 - Nature of the product (A): The tropylium cation is a planar, cyclic, fully conjugated system with 6 pi electrons (4n+2, n=1). By Huckel's rule it is aromatic. So statement (a) is CORRECT. Step 4 - Evaluate statement (b): The tropylium cation is a charged species (full positive charge delocalized over all 7 carbons). Charged ionic species typically have high dipole moments or are ionic in nature. Statement (b) saying it has high dipole moment is effectively correct for an ionic/charged species in solution context. Step 5 - Evaluate statement (c): The tropylium cation has very HIGH resonance energy because it is fully aromatic (6 pi electrons over 7 carbons, all equivalent by symmetry). Saying it has LESS resonance energy is INCORRECT - it actually has exceptionally HIGH resonance/delocalization energy due to aromaticity. This is the incorrect statement. Step 6 - Evaluate statement (d): The product is an ionic species (tropylium salt, tropylium nitrate after ion pairing). Ionic compounds are soluble in polar solvents. Statement (d) is CORRECT. Step 7 - Conclusion: Statement (c) claiming the product has less resonance energy is the incorrect statement, since the tropylium cation is aromatic and has very high resonance stabilization energy. Therefore, the correct answer is C.