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What I was understanding is that all bases are nucleophiles and acids are electrophiles means the condition for them is same and all nucleophiles are basic and all bases are nucleophiles and same for acid and electrophiles but my sir said that it isn't completely true . Can someone give me an example of electrophilic base / nucleophilic acid / acidic nucleophile / basic electrophile

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  • $\begingroup$ chemistry.stackexchange.com/questions/20061/… $\endgroup$
    – Mithoron
    Commented Oct 14, 2019 at 15:29
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    $\begingroup$ All these aren't inherent properties of compounds, but are relative and depend on situation. Some molecule may act as nucleophile/base/... While it's a common saying that for example H2SO4 is an acid, it's rather that it usually acts as one, but it can act also as base. If one says it is an acid it's rather because of human need for categorization then inherent property. $\endgroup$
    – Mithoron
    Commented Oct 14, 2019 at 15:34
  • $\begingroup$ chemistry.stackexchange.com/questions/20061/… $\endgroup$
    – Mithoron
    Commented Oct 14, 2019 at 15:36

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$\ce{HSO4-}$ is acidic ($\mathrm pK_\mathrm a = 1.99$) yet also reacts as a nucleophile e.g. in the acid-catalysed hydration of olefins, which according to my mechanism lecture procedes via a sulphate diester intermediate.

If I thought for long enough, I probably could come up with a basic compound that acts as an electrophile in a given situation.

However, having single counterexamples to a general trend isn’t necessarily helpful; it is better to understand the differences in terminology. For that, I would like to direct you to Ben’s answer in the linked question, that clearly highlights the difference between nucleophilicity (a kinetic phenomenon) and basicity (a thermodynamic phenomenon).

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