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Leaving Group Conversions - Sulfonyl Chlorides

Leaving Group Conversions - Sulfonyl Chlorides

12. Alcohols, Ethers, Epoxides and Thiols / Leaving Group Conversions - Sulfonyl Chlorides / Problem 3

Which atom in toluene sulfonyl chloride (TsCl) is electrophilic? Justify your answer.

ANSWERS OPTIONS

A

(i) C because the pi-system of the ring withdraws electrons, making it electron-deficient.

B

(ii) S because it is surrounded by electron-withdrawing groups, making it electron-deficient.

C

(iii) O because it can form resonance and has a negative charge, making it electron-rich.

D

(iv) Cl because it is the most electronegative atom, making it an electron-rich species.

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