NVAEasyJEE 2025Aromatic Compounds & Benzene

JEE Chemistry 2025 Question with Solution

The compound with molecular formula C6H6\mathrm{C_6H_6}, which gives only one monobromo derivative and takes up four moles of hydrogen per mole for complete hydrogenation has _____π\pi electrons.

Answer

Correct answer:6

Step-by-step solution

Standard Method

Given: The compound has molecular formula C6H6\mathrm{C_6H_6}, gives only one monobromo derivative, and shows aromatic character consistent with benzene.

Find: The number of π\pi electrons.

The compound with molecular formula C6H6\mathrm{C_6H_6} is benzene. Benzene has a cyclic conjugated structure with three double bonds represented in its resonance forms.

Each double bond contributes 22 π\pi electrons.

Total π electrons=3×2=6\text{Total } \pi \text{ electrons} = 3 \times 2 = 6

The fact that it gives only one monobromo derivative shows that all six hydrogen atoms are equivalent, which supports the benzene structure.

Therefore, the number of π\pi electrons is 66.

Using aromaticity idea

Given: An aromatic compound with formula C6H6\mathrm{C_6H_6} that gives only one monobromo derivative.

Find: The number of π\pi electrons.

Aromatic compounds follow Hückel's rule:

4n+24n + 2

For benzene,

4n+2=64n + 2 = 6

which corresponds to n=1n = 1. Hence benzene contains 66 π\pi electrons.

Therefore, the required numerical answer is 66.

Common mistakes

  • Assuming that the number of π\pi electrons equals the number of carbon atoms. This is wrong because π\pi electrons are counted from double bonds or conjugated p-orbitals, not directly from the carbon count. Count 22 π\pi electrons for each double bond instead.

  • Ignoring the clue that only one monobromo derivative is formed. This is wrong because that clue confirms that all ring hydrogens are equivalent, identifying the compound as benzene. Use this symmetry information to recognize the aromatic structure first.

  • Confusing hydrogenation data with direct counting of π\pi electrons. This is wrong because hydrogen uptake is only a structural clue here, while the actual π\pi-electron count comes from the conjugated double bonds. First identify the compound, then count the delocalized electrons.

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