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An organic compound 'X' with molecular ...

An organic compound 'X' with molecular formula `C_7H_8O` in insoluble in aqueous `NaHCO_3` but dissolved in NaOH. When treated with bromine water 'X' rapidly give 'Y' `(C_7H_5OBr)`. The compound 'X' and 'Y' respectively are

A

o - cresol

B

p - cresol

C

m - cresol

D

anisole

Text Solution

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The correct Answer is:
To solve the problem, we need to identify the organic compounds 'X' and 'Y' based on the given information. ### Step-by-Step Solution: 1. **Identify the Molecular Formula of Compound 'X':** The molecular formula of compound 'X' is given as C₇H₈O. 2. **Solubility in Aqueous NaHCO₃:** The problem states that compound 'X' is insoluble in aqueous NaHCO₃. This indicates that 'X' is not a carboxylic acid, as carboxylic acids typically react with NaHCO₃ (a weak base) to produce carbon dioxide gas. Therefore, 'X' is likely a phenolic compound or an alcohol. 3. **Solubility in NaOH:** Compound 'X' is soluble in NaOH, which is a strong base. This suggests that 'X' is a weak acid (like a phenol) since weak acids can dissolve in strong bases. 4. **Reaction with Bromine Water:** When treated with bromine water, compound 'X' gives compound 'Y' (C₇H₅OBr). The reaction with bromine water indicates that 'X' has an active site for bromination, typically found in phenolic compounds. 5. **Determine the Structure of 'X':** Given that 'X' is a phenolic compound with the formula C₇H₈O, a likely candidate is meta-cresol (or 3-methylphenol), which has the structure: - C₆H₄(OH)(CH₃) (where the hydroxyl group is on the benzene ring and the methyl group is in the meta position). 6. **Determine the Structure of 'Y':** The compound 'Y' has the formula C₇H₅OBr. Since 'Y' is formed by bromination of 'X', we can deduce that the bromine atoms are added to the ortho and para positions of the phenolic compound. The likely structure for 'Y' is 2,4,6-tribromo-3-methylphenol. 7. **Final Identification:** - Compound 'X' is meta-cresol (3-methylphenol). - Compound 'Y' is 2,4,6-tribromo-3-methylphenol. ### Summary: - **Compound 'X':** Meta-cresol (3-methylphenol) - **Compound 'Y':** 2,4,6-tribromo-3-methylphenol
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