draw-the-mechanism-for-the-given-reaction-using-tosylatei-explain-why-this-metho

Question

Draw the mechanism for the given reaction using tosylate.

(i) Explain why this method is not the most sustainable.

(ii) Determine the reagent we use instead of tosylate.

Accepted Answer

(i) The reaction with tosylate, a toxic and corrosive reagent, produces another toxic and corrosive by-product contributing to waste generation.

(ii) SOCl₂ or PCl₃

Answer

(i) The reaction with tosylate, a toxic and corrosive reagent, produces another toxic and corrosive by-product contributing to waste generation.

(ii) HCl and PCC, CH₂Cl₂

Answer

(i) The reaction with tosylate, produces a less reactive and nontoxic by-product.

(ii) SOCl₂ and PCC, CH₂Cl₂

Answer

(i) The reaction with tosylate uses a bulky reagent, which is not ideal.

(ii) SOCl₂ or PCl₃