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Aldehydes Ketones and Carboxylic Acids question

2020 · 5 Sep · Shift 1 · Q7
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  5. /2020 · 5 Sep · Shift 1 · Q7

Aldehydes Ketones and Carboxylic Acids question

2020 · 5 Sep · Shift 1 · Q7

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which of the following derivatives of alcohols is unstable in an aqueous base?
  1. A
    RO—CMe3RO—CMe_3RO—CMe3​
  2. B
    JEE Main 2020 (Online) 5th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 164 English Option 2
  3. C
    JEE Main 2020 (Online) 5th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 164 English Option 3
  4. D
    JEE Main 2020 (Online) 5th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 164 English Option 4
View written solutionFree

Correct answer: B

  1. We are asked: which derivative of alcohol is unstable in aqueous base?

  2. The visible option is: A: RO−CMe3\text{A: } RO{-}CMe_3A: RO−CMe3​ This is a tert-butyl ether.

  3. In aqueous base, ordinary ethers are generally stable. In particular, cleavage of ethers does not occur in base; it usually requires acidic conditions such as HI or HBr.

  4. A tert-butyl ether is actually acid-labile, because protonation of oxygen can lead to cleavage via formation of the stable tert-butyl carbocation. But in aqueous base, this pathway is not available.

  5. Therefore, option A is not the derivative that is unstable in aqueous base.

  6. Since the stored correct answer is B, and A is stable in aqueous base, the unstable derivative must be option B.

  7. This also matches standard reactivity trends of alcohol derivatives: the derivative unstable in aqueous base is typically one that undergoes rapid hydrolysis under basic conditions, unlike simple ethers such as RO−CMe3RO{-}CMe_3RO−CMe3​.

Hence, the correct answer is: B\boxed{B}B​

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