1. Carboxylate ion ($\ce{RCOO-}$) is a weak base as the negative charge on oxygen is delocalised due to resonance. So, it has less tendency to donate lone pair of electrons to H+ ion. Similarly, it has less tendency to donate lone pair of electrons to a carbocations. But in my textbook, it is given that, it acts as a weak base but strong nucleophile. Why does it act as strong nucleophile?

  2. LDA (lithiumdiisopropylamide) is a strong bulky base. Why it is considered as a weak nucleophile?

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    $\begingroup$ Nucleophilicity and basicity aren't the same concept. $\endgroup$ – Zhe May 2 '18 at 13:52
  • $\begingroup$ Nucleophilicity is tendency of a nucleophile to donate electron pair to carbocation,isn't it ? $\endgroup$ – sai saandeep May 2 '18 at 14:06
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    $\begingroup$ Nucleophilicity is a kinetic concept. Basicity could be kinetic or thermodynamic. $\endgroup$ – Zhe May 2 '18 at 15:23
  • $\begingroup$ Sorry sir. I didn't understand you. $\endgroup$ – sai saandeep May 2 '18 at 15:50
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    $\begingroup$ Right. And I think that's your problem. You're confusing two separate concepts that have some overlap. One does not imply the other or vice versa. $\endgroup$ – Zhe May 2 '18 at 17:08

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