JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Arrange the following compounds in increasing order of C–OH bond length : methanol, phenol, p-ethoxyphenol
- Aphenol < methanol < p-ethoxyphenol
- Bmethanol < p-ethoxyphenol < phenol
- Cmethanol < phenol < p-ethoxyphenol
- Dphenol < p-ethoxyphenol < methanol
View written solutionFree
Correct answer: D
-
Key idea: The bond length decreases when the carbon attached to has more double-bond character.
-
Methanol
- In methanol, the bond is .
- There is no resonance involving this bond.
- So it is a normal single bond, hence relatively longest.
-
Phenol
- In phenol, the bond is between oxygen and an carbon of the benzene ring.
- Lone pair on oxygen participates in resonance with the aromatic ring:
- Thus the bond gets partial double-bond character, making it shorter than in methanol.
-
-Ethoxyphenol
- This has another substituent, , at the para position.
- The ethoxy group is a (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 bond in -ethoxyphenol has slightly less partial double-bond character than in phenol.
- So its bond is longer than phenol, but still shorter than methanol.
-
Increasing order of bond length:
-
Check options:
- A: ❌
- B: ❌
- C: ❌
- D: ✅
Therefore, the correct option is D.
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