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An organic compound [X]. C(5)H(8)O react...

An organic compound [X]. `C_(5)H_(8)O` reacts with hydroxylamine to form [Y]. In the presence of conc. `H_(2)SO_(4)` gives `delta`-lactam. [X] neither give Benedicts test nor it respond positively towards haloform test. The compound [X] is

A

B

C

D

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 C5H8O that reacts with hydroxylamine and forms a delta-lactam in the presence of concentrated sulfuric acid. Let's break down the information step by step. ### Step-by-Step Solution: 1. **Determine the Degree of Unsaturation (DU)**: - The formula for calculating the degree of unsaturation (DU) is: \[ DU = \frac{C + 1 - H}{2} \] - For [X], we have: - C = 5 - H = 8 - Therefore, \[ DU = \frac{5 + 1 - 8}{2} = \frac{-2}{2} = 2 \] - This indicates that there are two degrees of unsaturation, which could correspond to either two double bonds, one triple bond, or a ring structure. **Hint**: Remember that each degree of unsaturation corresponds to a ring or a double bond. 2. **Analyze the Reactivity**: - The compound [X] reacts with hydroxylamine (NH2OH) to form [Y]. This suggests that [X] is likely a ketone or an aldehyde since they typically react with hydroxylamine to form oximes. - The fact that [X] does not give a Benedict's test indicates that it is not an aldehyde (as aldehydes are typically oxidized by Benedict's reagent). - Therefore, [X] is likely a ketone. **Hint**: Aldehydes give positive results in Benedict's test, while ketones do not. 3. **Consider the Haloform Test**: - The haloform test is positive for methyl ketones (ketones with a CH3 group adjacent to the carbonyl). Since [X] does not respond positively to this test, it cannot be a methyl ketone. - This further supports that [X] is a ketone without a methyl group adjacent to the carbonyl. **Hint**: The haloform test is specific for methyl ketones; if the test is negative, the structure must be different. 4. **Formation of Delta-Lactam**: - When [X] is treated with concentrated sulfuric acid, it forms a delta-lactam. This suggests that [X] must have a structure that can undergo a rearrangement to form a cyclic amide. - The presence of a delta-lactam indicates that the starting compound [X] likely has a cyclic structure. **Hint**: Delta-lactams are cyclic amides formed from amino acids or cyclic ketones. 5. **Identify the Compound**: - Given that [X] is a ketone with 5 carbons, does not give a haloform test, and can form a delta-lactam, the most likely candidate is cyclopentanone. - Cyclopentanone has the formula C5H8O, fits the criteria of not being a methyl ketone, and can undergo the necessary reactions to form a delta-lactam. **Hint**: Look for cyclic structures with the correct number of carbons and functional groups that match the given reactions. ### Conclusion: The compound [X] is **cyclopentanone**.
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