Hydrocarbon (A) `C_(6)H_(10)` on treatment with `H_(2)/Ni, H_(2)//`Lindlar's catalyst or `Na//`liq. `NH_(3)` forms three different reduction products (B), (C), (D) respectively. (A) does not form any salt with ammonical `AgNO_(3)` solution, but (E) forms salt on heating with `NaNH_(2)` in an inert solvent. Compound (E) reacts with `CH_(3)l` to give (F). Compound (D) on oxidative ozonolysis gives n-butanoic acid along with other product.
(F) on ozonolysis will produce -

Options

A. acetic aicd
B. formic acid
C. propanoic acid
D. formaldehyde

Answer

To solve the problem step-by-step, we will analyze the hydrocarbon (A) with the molecular formula \(C_6H_{10}\) and deduce the products formed through various reactions.

### Step 1: Identify Hydrocarbon (A)
Given that hydrocarbon (A) has the formula \(C_6H_{10}\), it can be either a cycloalkene or an alkyne. Since (A) does not form a salt with ammonical \(AgNO_3\), it indicates that (A) is a non-terminal alkyne (terminal alkynes form salts with ammonical \(AgNO_3\)). Thus, we can represent (A) as:
\[ \text{(A) } CH_3CH_2C \equiv CCH_3 \]

### Step 2: Reduction of (A) to form (B), (C), and (D)
1. **Reduction with \(H_2/Ni\)**: This is a complete hydrogenation, converting the alkyne to an alkane:
\[ \text{(B) } CH_3CH_2CH_2CH_2CH_2CH_3 \quad \text{(Hexane)} \]

2. **Reduction with \(H_2\) using Lindlar's catalyst**: This leads to the formation of a cis-alkene:
\[ \text{(C) } CH_3CH_2CH_2C=CCH_3 \quad \text{(Cis-3-hexene)} \]

3. **Reduction with \(Na\) in liquid \(NH_3\)**: This is a Birch reduction, leading to the formation of a trans-alkene:
\[ \text{(D) } CH_3CH_2CH_2C=CH_2 \quad \text{(Trans-2-hexene)} \]

### Step 3: Formation of Compound (E)
When (A) reacts with \(NaNH_2\) in an inert solvent, it forms a sodium alkyne salt:
\[ \text{(E) } CH_3CH_2C \equiv CNa \]

### Step 4: Reaction of (E) with \(CH_3I\) to form (F)
When (E) reacts with \(CH_3I\), it forms a new alkyne:
\[ \text{(F) } CH_3CH_2C \equiv CH_3 \quad \text{(2-heptyne)} \]

### Step 5: Ozonolysis of Compound (D)
When compound (D) undergoes oxidative ozonolysis, it yields n-butanoic acid and another product:
\[ \text{(D) } CH_3CH_2CH_2C=CH_2 \xrightarrow{O_3} CH_3CH_2C(=O)OH \quad \text{(n-butanoic acid)} + \text{another product} \]

### Step 6: Ozonolysis of Compound (F)
When (F) undergoes ozonolysis, we can predict the products:
\[ \text{(F) } CH_3CH_2C \equiv CH_3 \xrightarrow{O_3} CH_3C(=O)OH + CH_3C(=O)OH \quad \text{(producing two equivalents of acetic acid)} \]

### Final Answer
Thus, the ozonolysis of (F) will produce:
\[ \text{Acetic acid (CH}_3COOH\text{)} \]