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JIPMER 2016
Exam
JIPMER
Year
2016
Subject
Chemistry
Chapter
Alcohols Phenols and Ethers

JIPMER 2016 · Chemistry · Alcohols Phenols and Ethers

Ethers like ROR can be cleaved by concentrated HI but not by HCl...

Ethers like ROR can be cleaved by concentrated HI but not by HCl becauseEthers like ROR can be cleaved by concentrated HI but not by HCl because

Options

  1. AI−\mathrm{I}^{-}is a weaker nucleophile than Cl−\mathrm{Cl}^{-}
  2. BI−\mathrm{I}^{-}is stronger nucleophile than Cl−\mathrm{Cl}^{-}
  3. CSN1S_N 1 mechanism carried out in this reaction is rapidly in presence of HI
  4. DNone of the above

Correct answer

B. I−\mathrm{I}^{-}is stronger nucleophile than Cl−\mathrm{Cl}^{-}

Step-by-step solution

The cleavage of ether (ROR)(R O R) by a halogen hydracid is eventually a SN2S_N 2 type displacement where halide ion (X−)\left(X^{-}\right)acts as a nucleophile. Since, I−\mathrm{I}^{-}is a very strong nucleophile compared to Cl−\mathrm{Cl}^{-}, reaction easily occurs when HI is used and not by HCl . Ethers like ROR can be cleaved by concentrated HI but not by HCl because
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