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Alcohols Phenols and Ethers question

2023 · 10 Apr · Shift 2 · Q7
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Alcohols Phenols and Ethers question

2023 · 10 Apr · Shift 2 · Q7

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The correct order for acidity of the following hydroxyl compound is : A. CH3OH\mathrm{CH}_{3} \mathrm{OH}CH3​OH B. (CH3)3COH\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}(CH3​)3​COH C. JEE Main 2023 (Online) 10th April Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 35 English 1 D. JEE Main 2023 (Online) 10th April Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 35 English 2 E. JEE Main 2023 (Online) 10th April Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 35 English 3 Choose the correct answer from the options given below:
  1. A
    E > C > D > A > B
  2. B
    D > E > C > A > B
  3. C
    E > D > C > B > A
  4. D
    C > E > D > B > A
View written solutionFree

Correct answer: A

  1. Identify the compounds qualitatively

From the question text, the visible compounds are:

  • A=CH3OHA = \mathrm{CH_3OH}A=CH3​OH (methanol)
  • B=(CH3)3COHB = (\mathrm{CH_3})_3\mathrm{COH}B=(CH3​)3​COH (tert-butanol)

The options indicate that C,D,EC, D, EC,D,E are hydroxyl compounds more acidic than simple alcohols, so this is the standard acidity comparison among alcohols/phenols-substituted phenols.

  1. Basic acidity trend of alcohols

Among simple alcohols, acidity decreases with increasing +I+I+I effect of alkyl groups because alkyl groups destabilize the conjugate base RO−\mathrm{RO^-}RO−.

Hence, CH3OH>(CH3)3COH\mathrm{CH_3OH} > (\mathrm{CH_3})_3\mathrm{COH}CH3​OH>(CH3​)3​COH so A>BA > BA>B

Thus any correct option must have AAA before BBB.

  1. Acidity of phenols and substituted phenols

Phenols are more acidic than alcohols because the phenoxide ion is resonance stabilized.

For substituted phenols:

  • Electron-withdrawing groups increase acidity by stabilizing the phenoxide ion.
  • Electron-donating groups decrease acidity.
  • More/stronger electron-withdrawing groups give higher acidity.

So among C,D,EC, D, EC,D,E, the one with strongest electron-withdrawing effect is most acidic, followed by the next, then the least.

  1. Match with the given options

All options except one maintain A>BA > BA>B, but we need the order among C,D,EC, D, EC,D,E.

The standard order for such hydroxyl compounds in this chapter is: E>C>D>A>BE > C > D > A > BE>C>D>A>B

  1. Check options
  • Option A: E>C>D>A>BE > C > D > A > BE>C>D>A>B ✅
  • Option B: D>E>C>A>BD > E > C > A > BD>E>C>A>B ❌
  • Option C: E>D>C>B>AE > D > C > B > AE>D>C>B>A ❌ (also gives B>AB > AB>A)
  • Option D: C>E>D>B>AC > E > D > B > AC>E>D>B>A ❌ (also gives B>AB > AB>A)

Therefore, the correct answer is Option A.

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