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A compound 'A' having the molecular for...

A compound 'A' having the molecular formula `C_(5)H_(12)O`, on oxidation gives a compound 'B' with molecular formula `C_(5)H_(10)O`. Compound 'B' gave a 2, 4- dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound 'A' is

A

`CH_(3)-CH_(2)-CH_(2)-CH_(2)-CH_(2) -OH`

B

`CH_(3)-CH_(2)-CH_(2)-underset(OH) underset(|)(CH) -CH_(3)`

C

`CH_(3)-CH_(2)-underset(OH)underset(|)(CH)-CH_(2)-CH_(3)`

D

`CH_(3)-CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)-OH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the structure of compound 'A' with the molecular formula C5H12O, we follow these steps: ### Step 1: Analyze the Molecular Formula The molecular formula of compound 'A' is C5H12O. This indicates that it is likely an alcohol or an ether, as it contains an -OH group. **Hint:** Look for functional groups that can be present in the compound based on its molecular formula. ### Step 2: Understand the Oxidation Reaction Upon oxidation, compound 'A' yields compound 'B' with the molecular formula C5H10O. The loss of two hydrogen atoms during oxidation suggests that 'A' is likely a secondary alcohol, which oxidizes to a ketone. **Hint:** Remember that oxidation typically involves the removal of hydrogen or the addition of oxygen. ### Step 3: Identify Compound 'B' Compound 'B' gives a 2,4-dinitrophenylhydrazine derivative. This indicates that 'B' is either an aldehyde or a ketone. However, since it does not give a haloform test or a silver mirror test, it confirms that 'B' is a ketone. **Hint:** Recall the tests that distinguish between aldehydes and ketones. ### Step 4: Evaluate the Options 1. **Option 1: Pentan-1-ol** - Oxidizes to pentanal (an aldehyde), which would give a silver mirror test. This option is incorrect. 2. **Option 2: Pentan-2-ol** - Oxidizes to pentan-2-one (a ketone), but it contains a methoxy group, which can give a haloform test. This option is also incorrect. 3. **Option 3: Pentan-3-ol** - Oxidizes to pentan-3-one (a ketone) and does not contain any methoxy group, thus it will not give a haloform test or a silver mirror test. This option is correct. **Hint:** Eliminate options based on the tests they would pass or fail. ### Conclusion The structure of compound 'A' is **Pentan-3-ol** (C5H12O). Upon oxidation, it forms **Pentan-3-one** (C5H10O), which fits all the criteria given in the problem. **Final Answer:** The structure of compound 'A' is Pentan-3-ol.

To determine the structure of compound 'A' with the molecular formula C5H12O, we follow these steps: ### Step 1: Analyze the Molecular Formula The molecular formula of compound 'A' is C5H12O. This indicates that it is likely an alcohol or an ether, as it contains an -OH group. **Hint:** Look for functional groups that can be present in the compound based on its molecular formula. ### Step 2: Understand the Oxidation Reaction ...
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NCERT FINGERTIPS ENGLISH-ALDEHYDES, KETONES AND CARBOXYLIC ACIDS-MCQs( CHEMICAL REACTIONS )
  1. Identify (X), (Y) and (Z) reagents in the given sequence of reaction. ...

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  2. Which of the following does not answer iodoform test ?

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  3. A compound 'A' having the molecular formula C(5)H(12)O, on oxidation ...

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  4. To differentiate between pentan -2-one and pentan -3-one a test is ca...

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  5. An organic compound of molecular formula C(3)H(6)O did not give a silv...

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  6. Which is the correct method of synthesising acetamide from acetone?

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  7. Compound (X) with molecular formula C(3)H(8)O is treated with acidifie...

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  8. Which of the following compounds will give a coloured crystalline com...

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  9. Match the column I with column II and mark the appropriate choice .

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  10. Few simple chemical tests are given below to differentiate between the...

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  11. Which of the following will not give aldol condensation ?

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  12. The claisen schmidt condensation product of benzaldehyde and acetone i...

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  13. Study the following sequence of reaction and identify the product (Y)....

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  14. Identify (X), (Y) and (Z) in the given reaction. X +Y overset(Z) to ...

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  15. Propanal on treatment with dilute sodium hydroxide gives

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  16. Aldehydes that do not undergo aldol condensation are (1) propanal (...

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  17. The order of reactivity of CH(3)CHO, CH(3)COC(2)H(5) and CH(3)COCH(3) ...

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  18. The final product (Y) in the following sequence of chemical reaction i...

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  19. Which of the following is a correct statement ?

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  20. Which of the following is the most reactive isomer ?

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