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An organic compound 'X' is oxidized by u...

An organic compound 'X' is oxidized by using acidified `K_(2)Cr_(2)O_(7)`. The product obtained reacts with phenyl hydrazine but does not answer silver mirror test. The possible structure of 'X' is `:`

A

`CH_(3)COCH_(3)`

B

`(CH_3)_(2)CHOH`

C

`CH_(3)CHO`

D

`CH_(3)CH_(2)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question, we need to analyze the information provided about the organic compound 'X' and the reactions it undergoes. ### Step-by-Step Solution: 1. **Identify the Oxidation Reaction**: - The compound 'X' is oxidized using acidified \( K_2Cr_2O_7 \). This reagent is a strong oxidizing agent that can oxidize alcohols to ketones or carboxylic acids, depending on the type of alcohol. - We need to determine what type of compound 'X' could be to produce a ketone after oxidation. 2. **Determine the Product 'Y'**: - The product obtained from the oxidation of 'X' is denoted as 'Y'. Since 'Y' reacts with phenyl hydrazine but does not give a silver mirror test (which is indicative of aldehydes), we conclude that 'Y' must be a ketone. - Therefore, 'X' must be a secondary alcohol (since secondary alcohols are oxidized to ketones). 3. **Evaluate the Options**: - We have four options to consider for 'X': - A: \( CH_3COCH_3 \) (acetone) - This is already a ketone and would not be oxidized. - B: \( CH_3CHOHCH_3 \) (2-propanol) - This is a secondary alcohol that can be oxidized to acetone (a ketone). - C: \( CH_3CHO \) (acetaldehyde) - This is an aldehyde, which would be oxidized to acetic acid, not a ketone. - D: \( CH_3CH_2OH \) (ethanol) - This is a primary alcohol that would be oxidized to acetic acid, not a ketone. 4. **Confirm the Reaction with Phenyl Hydrazine**: - The ketone produced from the oxidation of 'X' (which we identified as 2-propanol) will react with phenyl hydrazine to form a phenylhydrazone. - The reaction proceeds as follows: \[ \text{Ketone} + \text{Phenylhydrazine} \rightarrow \text{Phenylhydrazone} + \text{Water} \] - Since 'Y' is a ketone, it will react with phenyl hydrazine, confirming that option B is correct. 5. **Final Conclusion**: - Since option B is the only one that fits all the criteria (oxidizes to a ketone, reacts with phenyl hydrazine, and does not give a silver mirror test), we conclude that the structure of 'X' is: \[ \text{B: } CH_3CHOHCH_3 \]
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