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 `(C)overset("Moist"Ag_(2)O)rarr(P)underset(CH_(2)Cl_(2))overset(PC C)rarr(Q)`
The product (Q) is

Options

A. formaldehyde
B. formic acid
C. ethanoic acid
D. acrylic acid

Answer

To solve the problem step-by-step, we will analyze the information provided and deduce the required product (Q).

### Step 1: Determine the empirical formula of the compound
1. **Combustion Data**: We have 0.108 g of an isomer that produces 0.308 g of CO₂ and 0.072 g of H₂O.
2. **Calculate moles of carbon and hydrogen**:
- From CO₂:
- Molar mass of CO₂ = 44 g/mol, thus moles of CO₂ = 0.308 g / 44 g/mol = 0.0070 mol.
- Moles of carbon = 0.0070 mol (since 1 mol of CO₂ contains 1 mol of C).
- From H₂O:
- Molar mass of H₂O = 18 g/mol, thus moles of H₂O = 0.072 g / 18 g/mol = 0.0040 mol.
- Moles of hydrogen = 0.0040 mol (since 1 mol of H₂O contains 2 mol of H, so 0.0040 mol H₂O gives 0.0080 mol H).
3. **Calculate moles of oxygen**:
- Total mass = 0.108 g, mass of C = 0.084 g (from 0.0070 mol C × 12 g/mol), mass of H = 0.008 g (from 0.0080 mol H × 1 g/mol).
- 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 mol.
4. **Empirical formula**:
- C: 0.0070 mol / 0.0010 mol = 7
- H: 0.0080 mol / 0.0010 mol = 8
- O: 0.0010 mol / 0.0010 mol = 1
- Therefore, the empirical formula is C₇H₈O.

### Step 2: Identify the isomers A and B
1. **Isomer A**: Insoluble in NaOH and NaHCO₃ suggests it is likely an ether or aromatic compound (anisol, C₇H₈O).
2. **Isomer B**: Soluble in NaOH indicates it is likely a phenol or alcohol.

### Step 3: Analyze the reactions of A and B
1. **Reaction of A with HI**:
- A (anisole) reacts with HI to form methyl iodide (C) and phenol (D).
- C (methyl iodide) is soluble in AgNO₃, while D (phenol) is soluble in NaOH.

### Step 4: Further reactions of C
1. **C reacts with moist Ag₂O**:
- C (methyl iodide) reacts with moist Ag₂O to form methanol (P).
2. **P reacts with PCC in CH₂Cl₂**:
- PCC oxidizes methanol (P) to formaldehyde (Q).

### Conclusion
The product (Q) is **formaldehyde** (HCHO).