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Arrange the following compounds in increasing order of C – OH bond length: methanol, phenol, p-ethoxyphenol

1. phenol < methanol < p-ethoxyphenol
2. methanol < p-ethoxyphenol < phenol
3. methanol < phenol < p-ethoxyphenol
4. phenol < p-ethoxyphenol < methanol

Correct answer: phenol < p-ethoxyphenol < methanol

Solution

The C – OH bond length is influenced by the electron-donating or withdrawing effects of substituents. In this case, phenol has a shorter bond due to resonance stabilization, while p-ethoxyphenol has a longer bond than phenol but shorter than methanol due to the electron-donating ethoxy group, making the order phenol < p-ethoxyphenol < methanol.

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