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Alcohols Phenols and Ethers question

2020 · 8 Jan · Shift 1 · Q3
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Alcohols Phenols and Ethers question

2020 · 8 Jan · Shift 1 · Q3

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Arrange the following compounds in increasing order of C–OH bond length : methanol, phenol, p-ethoxyphenol
  1. A
    phenol < methanol < p-ethoxyphenol
  2. B
    methanol < p-ethoxyphenol < phenol
  3. C
    methanol < phenol < p-ethoxyphenol
  4. D
    phenol < p-ethoxyphenol < methanol
View written solutionFree

Correct answer: D

  1. Key idea: The C–OH\text{C–OH}C–OH bond length decreases when the carbon attached to OH\text{OH}OH has more double-bond character.

  2. Methanol

    • In methanol, the bond is C(sp3)–O\text{C(sp}^3\text{)–O}C(sp3)–O.
    • There is no resonance involving this C–O\text{C–O}C–O bond.
    • So it is a normal single bond, hence relatively longest.
  3. Phenol

    • In phenol, the C–OH\text{C–OH}C–OH bond is between oxygen and an sp2\text{sp}^2sp2 carbon of the benzene ring.
    • Lone pair on oxygen participates in resonance with the aromatic ring: Ar–OH↔Ar=O+H\text{Ar–OH} \leftrightarrow \text{Ar=O}^{+}\text{H}Ar–OH↔Ar=O+H
    • Thus the C–O\text{C–O}C–O bond gets partial double-bond character, making it shorter than in methanol.
  4. ppp-Ethoxyphenol

    • This has another substituent, −OC2H5-\text{OC}_2\text{H}_5−OC2​H5​, at the para position.
    • The ethoxy group is a +M+M+M (electron-donating by resonance) group.
    • It donates electron density into the ring, which reduces the tendency of the phenolic oxygen lone pair to delocalize strongly into the ring.
    • Therefore, the phenolic C–OH\text{C–OH}C–OH bond in ppp-ethoxyphenol has slightly less partial double-bond character than in phenol.
    • So its C–OH\text{C–OH}C–OH bond is longer than phenol, but still shorter than methanol.
  5. Increasing order of C–OH\text{C–OH}C–OH bond length: phenol<p-ethoxyphenol<methanol\text{phenol} < p\text{-ethoxyphenol} < \text{methanol}phenol<p-ethoxyphenol<methanol

  6. Check options:

    • A: phenol<methanol<p-ethoxyphenol\text{phenol} < \text{methanol} < p\text{-ethoxyphenol}phenol<methanol<p-ethoxyphenol ❌
    • B: methanol<p-ethoxyphenol<phenol\text{methanol} < p\text{-ethoxyphenol} < \text{phenol}methanol<p-ethoxyphenol<phenol ❌
    • C: methanol<phenol<p-ethoxyphenol\text{methanol} < \text{phenol} < p\text{-ethoxyphenol}methanol<phenol<p-ethoxyphenol ❌
    • D: phenol<p-ethoxyphenol<methanol\text{phenol} < p\text{-ethoxyphenol} < \text{methanol}phenol<p-ethoxyphenol<methanol ✅

Therefore, the correct option is D.

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