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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Identify the major product of the following reaction sequence: CH ₃- CH ₂ SH [ (iii) H ₂ O ] (i) Dil. OH ⁻, (ii) Ethylene oxide Product

Options

  1. ACH ₃- CH ₂- S - CH ₂- CH ₂- OH
  2. BCH ₃- CH ₂- O - CH ₂- CH ₂- OH
  3. CCH ₃- CH ₂ O ⁻

Correct answer

A. CH ₃- CH ₂- S - CH ₂- CH ₂- OH

Step-by-step solution

In the first step, ethanethiol ( CH ₃- CH ₂ SH ) reacts with dilute OH ⁻ to form the ethanethiolate anion, as thiols are acidic enough to be deprotonated by hydroxide ions. CH ₃- CH ₂ SH + OH ⁻ CH ₃- CH ₂ S ⁻ + H ₂ O In the second step, the ethanethiolate anion acts as a strong nucleophile and attacks a carbon atom of ethylene oxide via an S _ N 2 mechanism, leading to the opening of the strained three-membered ring. CH ₃- CH ₂ S ⁻ + Ethylene oxide CH ₃- CH ₂- S - CH ₂- CH ₂- O ⁻ In the final step, the resulting al

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