An organic compound 'A' with empirical formula $\mathrm{C}_{6} \mathrm{H}_{6} \mathrm{O}$ gives sooty flame on burning. Its reaction with bromine solution in low polarity solvent results in high yield of B. B is

JEE Main · 2023 · 31 Jan 2023 · Shift 1 · Hydrocarbons

An organic compound 'A' with empirical formula

C_{6} H_{6} O

gives sooty flame on burning. Its reaction with bromine solution in low polarity solvent results in high yield of B. B is

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

The compound

C X_{6} H X_{6} O

that burns with a sooty flame is the aromatic compound phenol. In a solvent of low polarity the bromine is only weakly polarised, so monosubstitution takes place; the hydroxyl group directs to the ortho and para positions and, para being favoured on steric grounds, the major product is 4-bromophenol. B is p-bromophenol.

JEE Main · 2023 · 31 Jan 2023 · Shift 1 · Single correct option

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