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
- ACH ₃- CH ₂- S - CH ₂- CH ₂- OH
- BCH ₃- CH ₂- O - CH ₂- CH ₂- OH
- 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