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How do I determine if a nucleophile attacks the electrophilic atom directly or indirectly? For instance a nucleophile could attack the carbon in a molecule with a carbonyl directly, but in another example the nucleophile might only attack the nucleophilic atom after attacking a hydrogen first (deprotonation). Thank you in advance!

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  • $\begingroup$ Hard-Soft Acid-Base Theory provides rules of thumb to predict which electrophilic atom a given nucleophile will attack. But pattern recognition/memorization is also useful. $\endgroup$ May 27, 2022 at 18:19
  • $\begingroup$ Ultimately only experimental data is definative. One can make predictions but until they are backed by experiment they remain "best gueses". $\endgroup$
    – Waylander
    May 27, 2022 at 19:47

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