Quote from a textbook (Organic chemistry, Fourth Edition by Paula Yurkanis Bruice):

"A weaker base is a more electronegative base; that is, it is better able to accommodate its negative charge. Thus, weaker bases are better at withdrawing electrons inductively from the carbonyl carbon; electron withdrawal increases the carbonyl carbon’s susceptibility to nucleophilic attack."

Iodide is a weaker base than fluoride. So according to the textbook quote, iodide has a greater electron withdrawing ability than fluoride.

But the iodine atom is less electronegative than fluorine atom. How is it that the iodide ion is more electron withdrawing?

  • 2
    $\begingroup$ Iodine is not more withdrawing. This textbook is wrong in this quotation. $\endgroup$ – Mithoron May 31 '20 at 17:36

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