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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Which is a stronger nucleophile in aprotic solvent: water or hydrogen sulfide?

Which one is the stronger nucleophile in aprotic solvent: $\ce{H2O}$ or $\ce{H2S}?$ According to my notes, nucleophilicity order is directly proportional to basicity order in an aprotic medium, and is inversely proportional to basicity order in…
student
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Reactivity towards nucleophillic addition

Phenyl ethanal or ethanal I thought phenyl methanal is less reactive towards nucleophilic attack due to presence of bulky group. But answer in my book suggest ethanal is less reactive. Para-methoxybenzaldehyde vs para-methylbenzaldehyde. in…
Bhavay
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Nucleophilicity methanol vs water

I have a short question: Which among Methanol and water will be a better nucleophile for a reaction carried out in some polar protic solvent . Searching over the internet suggests that methoxide ion may be more nucleophilic than hydroxide ion, is…
Dhvanit
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Why is N- a better nucleophile than S-?

I can't rationalize why S- is a worse nucleophile than N-. I thought nucelophilicity was related to electronegativity, the more electronegative an atom is, the less of a nucleophile it is. Sulfur is less electronegative than Nitrogen. What concept…
ReftPowered
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Who makes a better nucleophile? CH3O- or OH-?

My argument is that the +I effect of CH3 group increases the electron density at oxygen atom, making it a better nucleophile
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Which one is the stronger nucleophile? CH3CH2O or CH3CO2

Not really sure what the principle would be. Maybe it has something to do with the resonance capability of the two Os in CH3CO2