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An organic compound X with molecular for...

An organic compound X with molecular formula `C_6H_10`, when treated with HBr, forms a gem dibromide. The compound X upon warming with `HgSO_4` and dil. `H_2SO_4`, produces a ketone which gives a positive iodoform test. The compound X is

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Text Solution

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The correct Answer is:
To solve the problem, we need to identify the organic compound X with the molecular formula C₆H₁₀ based on the given reactions and properties. ### Step-by-Step Solution: 1. **Understanding the Molecular Formula**: - The molecular formula of the compound is C₆H₁₀. - We can calculate the degree of unsaturation (DU) using the formula: \[ \text{DU} = \frac{C - H + X}{2} + 1 \] where C is the number of carbon atoms, H is the number of hydrogen atoms, and X is the number of halogen atoms. - For C₆H₁₀, we have: \[ \text{DU} = \frac{6 - 10 + 0}{2} + 1 = \frac{-4}{2} + 1 = -2 + 1 = -1 \] - This indicates that there are 2 degrees of unsaturation, which could imply the presence of a triple bond or two double bonds. 2. **Reaction with HBr**: - The compound X forms a geminal dibromide when treated with HBr. - A geminal dibromide means that both bromine atoms are attached to the same carbon atom. This suggests that X likely has a double or triple bond. 3. **Reaction with HgSO₄ and Dilute H₂SO₄**: - The compound X, when warmed with HgSO₄ and dilute H₂SO₄, produces a ketone that gives a positive iodoform test. - The iodoform test is positive for methyl ketones (RCOCH₃), indicating that the ketone formed must have a methyl group adjacent to the carbonyl carbon. 4. **Identifying Possible Structures**: - Given the information, we can deduce that X must be an alkyne (due to the presence of a triple bond) that can produce a methyl ketone upon hydration. - The structure of X should be 3-heptyne (C₆H₁₀), which can be represented as: \[ \text{CH}_3C \equiv CCH_2CH_3 \] 5. **Confirming the Structure**: - When 3-heptyne reacts with HBr, it will add across the triple bond to form a geminal dibromide. - When treated with HgSO₄ and dilute H₂SO₄, it will yield 2-pentanone (a methyl ketone), which gives a positive iodoform test. ### Conclusion: The compound X is **3-heptyne**.
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