An organic compound containing C, H and O gives following observations:
(i) It exists in two isomeric forms (A) and (B).
(ii) 0.108 g of one of the isomers on combustion gave 0.308 g of `CO_(2)` and 0.072 g of `H_(2)O`
(iii) (A) is insoluble in NaOH and `NaHCO_(3)` while (B) is soluble in NaOH.
(iv) (A) reacts with Hl to give compound (C ) and (D). (C ) can be separated from (D) by ethanolic `AgNO_(3)` solution and (D) is soluble in NaOH.
(v) (B) readily reacts with bromine water to give compound (E) of molecular formula `C_(7)H_(5)OBr_(3)`
Compound `(D)underset((iii)HCl)underset(4-7" atm,"125K)overset((i)NaOH)overset((ii)CO_(2))rarr(X)overset(CH_(3)COCl)rarr(Y)`
The product (Y) is

Options

A. an antiseptic
B. an antiallergic
C. an antipyretic
D. an antibiotic

Answer

To solve the problem step by step, we will analyze the information provided and derive the necessary conclusions.

### Step 1: Determine the empirical formula of the compound
Given that 0.108 g of one of the isomers on combustion produces:
- 0.308 g of CO₂
- 0.072 g of H₂O

**Calculating moles of carbon and hydrogen:**
1. **Moles of Carbon (C)**:
- From CO₂: 1 mole of CO₂ contains 1 mole of C.
- Molar mass of CO₂ = 44 g/mol.
- Moles of CO₂ = 0.308 g / 44 g/mol = 0.0070 moles of CO₂.
- Therefore, moles of C = 0.0070 moles.

2. **Moles of Hydrogen (H)**:
- From H₂O: 1 mole of H₂O contains 2 moles of H.
- Molar mass of H₂O = 18 g/mol.
- Moles of H₂O = 0.072 g / 18 g/mol = 0.0040 moles of H₂O.
- Therefore, moles of H = 2 × 0.0040 moles = 0.0080 moles.

3. **Calculating moles of Oxygen (O)**:
- Total mass = 0.108 g.
- Mass of C = 0.0070 moles × 12 g/mol = 0.084 g.
- Mass of H = 0.0080 moles × 1 g/mol = 0.008 g.
- Mass of O = Total mass - (mass of C + mass of H) = 0.108 g - (0.084 g + 0.008 g) = 0.016 g.
- Moles of O = 0.016 g / 16 g/mol = 0.0010 moles.

### Step 2: Determine the empirical formula
Now we have:
- C: 0.0070 moles
- H: 0.0080 moles
- O: 0.0010 moles

**Dividing by the smallest number of moles (0.0010):**
- C: 0.0070 / 0.0010 = 7
- H: 0.0080 / 0.0010 = 8
- O: 0.0010 / 0.0010 = 1

Thus, the empirical formula is C₇H₈O.

### Step 3: Analyze the isomers A and B
- **Isomer A** is insoluble in NaOH and NaHCO₃, indicating it is likely an ether or an aromatic compound (like anisol).
- **Isomer B** is soluble in NaOH, indicating it is likely a phenol or alcohol.

### Step 4: Reactions of Isomers
- **Isomer A (Anisol)** reacts with HI to form methyl iodide (C) and phenol (D).
- **Isomer B** reacts with bromine water, indicating it has a double bond and forms a compound E with the formula C₇H₅OBr₃.

### Step 5: Reaction of Compound D
- Compound D (phenol) reacts with NaOH and CO₂ to give the sodium salt of salicylic acid (X).
- X reacts with HCl to form salicylic acid.
- Salicylic acid (X) reacts with CH₃COCl to form aspirin (Y).

### Step 6: Identify the final product Y
The product Y is aspirin, which is known to be an antipyretic.

### Final Answer
The product (Y) is an antipyretic.

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