Catalytic hydrogenation of which of the following gives a product that further gives three photochemical monochlorination products (considering structural isomers only )?

Options

A.
B.
C.
D.

Explanation

To solve the question regarding the catalytic hydrogenation and subsequent photochemical monochlorination of the given compounds, we will follow these steps:

### Step 1: Identify the Compounds
We need to analyze the compounds provided in the question. Let's denote them as A, B, C, and D.

### Step 2: Perform Catalytic Hydrogenation
For each compound, we will perform catalytic hydrogenation. This process involves the addition of hydrogen (H₂) across the double bonds (alkenes) to convert them into alkanes (single bonds).

- **Compound A**: After hydrogenation, it becomes an alkane.
- **Compound B**: After hydrogenation, it also becomes an alkane.
- **Compound C**: After hydrogenation, it becomes an alkane.
- **Compound D**: After hydrogenation, it becomes an alkane.

### Step 3: Analyze Monochlorination
Next, we will treat each hydrogenated compound with Cl₂ in the presence of light (Hν) to perform monochlorination. We will count the number of structural isomers produced.

#### For Compound A:
- After hydrogenation, let's assume it has 2 different types of hydrogen atoms.
- Monochlorination can occur at these positions, but we find that it leads to only **2 unique products**.

#### For Compound B:
- After hydrogenation, it has 3 different types of hydrogen atoms.
- Monochlorination can occur at these positions, leading to **3 unique products**.

#### For Compound C:
- After hydrogenation, it has 3 different types of hydrogen atoms.
- Monochlorination can occur at these positions, leading to **3 unique products**.

#### For Compound D:
- After hydrogenation, it has multiple types of hydrogen atoms.
- Monochlorination can occur at various positions, leading to more than **3 unique products**.

### Step 4: Conclusion
Based on the analysis:
- Compound B and Compound C yield **3 unique monochlorination products**.
- Compound A yields **2 unique products**.
- Compound D yields more than **3 unique products**.

Thus, the answer to the question is that **the catalytic hydrogenation of Compound B or Compound C gives a product that further gives three photochemical monochlorination products**.

### Final Answer:
**B and C are the correct options.**

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