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An organic compound (A) with molecular f...

An organic compound (A) with molecular formula `C_(7)H_(8)O` dissolves in NaOH and gives characteristic colour with `FeCl_(3)`. On treatment with `Br_(2)`, it gives a tribromo product `C_(7)H_(5)OBr_(3)`. The compound is:

A

o-cresol

B

m- cresol

C

p-cresol

D

either of the three

Text Solution

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The correct Answer is:
To solve the problem step by step, let's analyze the information given in the question: ### Step 1: Identify the properties of the compound A The molecular formula of the compound A is C7H8O. The fact that it dissolves in NaOH suggests that it is likely a phenolic compound. Phenolic compounds contain a hydroxyl group (-OH) attached to an aromatic ring, which makes them soluble in basic solutions. **Hint:** Look for functional groups that indicate solubility in NaOH. ### Step 2: Characteristic color with FeCl3 The compound also gives a characteristic color with FeCl3 (ferric chloride). This is a typical reaction for phenolic compounds, which form colored complexes with ferric ions. This further confirms that compound A is a phenolic compound. **Hint:** Remember that phenols react with FeCl3 to form colored complexes. ### Step 3: Reaction with Br2 The next important point is that when treated with bromine (Br2), the compound yields a tribromo product with the formula C7H5OBr3. The formation of a tribromo compound indicates that three hydrogen atoms on the aromatic ring have been substituted by bromine atoms. **Hint:** Consider how many positions on the aromatic ring are available for substitution. ### Step 4: Determine the structure of the compound Since the compound is phenolic and gives a tribromo product, we can deduce that the hydroxyl group is activating and directs bromination to the ortho and para positions. However, since we get a tribromo product, it suggests that the meta position is more favored for substitution in this case. **Hint:** Analyze the positions of substitution on the aromatic ring based on the activating effects of the -OH group. ### Step 5: Identify the specific compound Given the molecular formula C7H8O and the characteristics of the reactions, the compound is likely to be meta-cresol (or meta-cresylic acid). This is because: - It has a -OH group (making it a phenolic compound). - It can undergo tribromination at the meta position, leading to the formation of C7H5OBr3. **Hint:** Compare the possible structures of cresols (ortho, meta, and para) to determine which one fits the given reactions. ### Conclusion Thus, the compound A is identified as **meta-cresol**. **Final Answer:** The compound is meta-cresol.
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