A compound (A) has molecular formula `C_(5)H_(9)CI` It does not react with bromine in `C CI_(4)` On treatment with a strong base it produces a single compound (B) (B) has a molecular formula `C_(5)H_(8)` and reacts with Baeyer's reagent . Reductive ozonotysis of (B) produces a compound (C ) which has a molecular formula `C_(5)H_(8) O_(2)`
What would be the oxidative ozonolysis product of B ?

Options

A.
B.
C.
D.

Answer

To solve the problem step by step, we will analyze the given information about the compounds A, B, and C, and deduce the oxidative ozonolysis product of compound B.

### Step 1: Analyze Compound A
- **Molecular Formula**: C₅H₉Cl
- **Reactivity**: It does not react with bromine in CCl₄, indicating that it is not an alkene or alkyne. This suggests that compound A is likely a saturated compound, possibly a haloalkane.
- **Degree of Unsaturation (DU)**:
\[ \text{DU} = \frac{(C + 1) - H}{2} = \frac{(5 + 1) - 9}{2} = \frac{6 - 9}{2} = \frac{-3}{2} \text{ (not possible)} \]
This calculation indicates that there is 1 degree of unsaturation, which suggests a ring structure (cyclopentane derivative).

### Step 2: Identify Compound B
- **Reaction with Strong Base**: Compound A reacts with a strong base to produce compound B (C₅H₈).
- **Molecular Formula of B**: C₅H₈ indicates that B has one less hydrogen than A, suggesting that a hydrogen was eliminated (dehydrohalogenation).
- **Reactivity**: B reacts with Baeyer's reagent (KMnO₄), indicating that it is an alkene.

### Step 3: Reductive Ozonolysis of B
- **Reductive Ozonolysis**: This reaction breaks double bonds and forms carbonyl compounds.
- **Product C**: The molecular formula of C is C₅H₈O₂, which suggests that B is likely a compound with a double bond that, upon ozonolysis, produces two carbonyl groups (aldehydes or ketones).

### Step 4: Determine the Structure of B
- Given that B is an alkene (C₅H₈) and has 1 degree of unsaturation, it could be cyclopentene or a linear alkene.
- The structure of B could be 1-pentene or cyclopentene.

### Step 5: Perform Oxidative Ozonolysis of B
- **Oxidative Ozonolysis**: This reaction converts carbonyl groups to carboxylic acids.
- If B is cyclopentene, the oxidative ozonolysis will yield:
- Two carboxylic acids from the cleavage of the double bond.

### Step 6: Final Product of Oxidative Ozonolysis
- The oxidative ozonolysis of B (assuming it is cyclopentene) will yield:
- A dicarboxylic acid with the formula C₅H₈O₄, specifically 3,4-pentanedicarboxylic acid (glutaric acid).

### Conclusion
The oxidative ozonolysis product of compound B is a dicarboxylic acid.

### Final Answer
The oxidative ozonolysis product of B is **3,4-pentanedicarboxylic acid**.

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