Questions tagged [nucleophilicity]

For questions involving the nucleophilicity of a chemical species. Not to be confused with "basicity", use the [acid-base] tag instead.

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Nucleophilicity with respect to the solvent

I am currently studying nucleophilicity of molecules and am getting a set of conflicting information, so I wanted to clarify nucleophilicity trends with respect to solvent. Master Organic Chemistry ...
John Smith's user avatar
15 votes
2 answers
5k views

Is hydrazine a better nucleophile than ammonia?

Which is a better nucleophile, $\ce{NH3}$ or $\ce{NH2NH2}$? For the sake of limiting scope, I want an answer for behavior in a protic solvent though non-protic solvent answers are welcomed. My logic ...
Elon Musk's user avatar
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9 votes
3 answers
37k views

How to determine order of nucleophilicity among commonly used nucleophiles?

How to determine order of nucleophilicity among commonly used nucleophiles? For example, in Finklestein reaction, $\ce{NaI}$ (reagent) - taken in acetone (solvent) - displaces $\ce{SH-}$ ion from ...
Kinjal's user avatar
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0 votes
0 answers
532 views

Nucleophilic addition - Propanal vs Benzaldehyde

According to my school textbook, carbon atom of the carbonyl group benzaldehyde is less electrophilic than that of propanal because polarity of the carbonyl group is reduced in benzaldehyde due to ...
Anubhab Das's user avatar