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A compound (P) having molecular formula ...

A compound `(P)` having molecular formula `C_(6)H_(10)` contains two `DU`. It yields `Q(C_(6)H_(12))` when reacts with excess of `H_(2)` of the presence of `Ni`. On ozonolysis `P` gives cyclopentanone and compound `Y`.
The compound `Q` gives the number of of monochlorination products

A

`3`

B

`4`

C

`5`

D

`6`

Text Solution

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The correct Answer is:
To solve the problem step by step, we will analyze the information given about compound P, its reactions, and the resulting compound Q. ### Step 1: Analyze the Molecular Formula and Degree of Unsaturation - The molecular formula of compound P is \( C_6H_{10} \). - The degree of unsaturation (DU) is calculated using the formula: \[ \text{DU} = \frac{(2C + 2 + N - H - X)}{2} \] where \( C \) is the number of carbons, \( H \) is the number of hydrogens, \( N \) is the number of nitrogens, and \( X \) is the number of halogens. - For \( C_6H_{10} \): \[ \text{DU} = \frac{(2 \times 6 + 2 - 10)}{2} = \frac{(12 + 2 - 10)}{2} = \frac{4}{2} = 2 \] - This indicates that compound P has either two double bonds, one ring and one double bond, or two rings. **Hint for Step 1:** Remember that the degree of unsaturation helps determine the presence of rings or multiple bonds in the structure. ### Step 2: Determine the Structure of Compound P - Given that P yields cyclopentanone and another compound Y upon ozonolysis, we can deduce that P likely contains a cyclopentene structure. - If we assume P is a cyclic compound with a double bond, one possible structure is 1-cyclopentene with a substituent that allows for the formation of cyclopentanone upon ozonolysis. **Hint for Step 2:** Ozonolysis can help identify the fragments produced, which gives clues about the structure of the original compound. ### Step 3: Reaction of Compound P with Hydrogen - When P reacts with excess hydrogen (H2) in the presence of nickel, it becomes saturated, resulting in compound Q with the formula \( C_6H_{12} \). - This indicates that all double bonds in P are reduced, leading to a fully saturated compound Q. **Hint for Step 3:** The presence of a catalyst like nickel allows for the hydrogenation of double bonds, converting alkenes to alkanes. ### Step 4: Determine the Structure of Compound Q - The structure of Q can be derived from the structure of P. If P is 1-cyclopentene, Q could be cyclohexane or a substituted cyclohexane depending on the substituents on the cyclopentene. **Hint for Step 4:** Visualizing the structure of Q helps in identifying potential sites for chlorination. ### Step 5: Count Unique Monochlorination Sites in Compound Q - To find the number of unique monochlorination products, we need to identify the unique hydrogen atoms in Q that can be replaced by chlorine. - If Q is cyclohexane, it has 6 hydrogen atoms, but due to symmetry, not all chlorination will yield unique products. - The unique chlorination sites can be counted as follows: - If Q is cyclohexane, there are 6 positions, but due to symmetry, there are 2 unique sites (1,2- and 1,3- positions). **Hint for Step 5:** Consider the symmetry of the molecule when counting unique chlorination sites, as identical positions will yield the same product. ### Conclusion - The number of unique monochlorination products for compound Q is 4. **Final Answer:** The compound Q gives 4 unique monochlorination products.

To solve the problem step by step, we will analyze the information given about compound P, its reactions, and the resulting compound Q. ### Step 1: Analyze the Molecular Formula and Degree of Unsaturation - The molecular formula of compound P is \( C_6H_{10} \). - The degree of unsaturation (DU) is calculated using the formula: \[ \text{DU} = \frac{(2C + 2 + N - H - X)}{2} \] ...
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