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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Why is the carbon in carbonyl compunds a good acceptor in nuclephilic acyl substititon when we are putting electrons in a higher antibonding orbital?
Wouldn't moving electrons into the Π* anti-bonding orbital have destabilizing effects on the molecule?
Here is the source https://www.youtube.com/watch?v=rVVX0TCxzCY&t=67s
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Relation between formation of carbocation and availability of nucleophile
Many sources suggest that in SN1 reactions the leaving group first exits the molecule, and the resulting carbocation is subsequently attacked by the nucleophile, suggesting that there is no relation ...
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Nucleophilicity order in polar protic solvent
The relative nucleophilicity in polar protic solvents of the following is
$\pu{1)}$ $\ce{CH3CH2S-}$
$\pu{2)}$ $\ce{CH3CH2O-}$
$\pu{3)}$ $\ce{CH3COO-}$
This is a question from my problem book. As per ...
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Which is more nucleophilic: acetamide or aniline?
Which compound will be more nucleophilic, knowing that the electron pair will be more delocalized in the ring for aniline? On the contrary, for the acetamide the electron pair will only be delocalized ...
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Secondary alkyl halides and strong base: Sn2 vs E2
I got this question from the PYQs of a college entrance exam. According to the answer key, 4-chloro-3-methylpent-1-ene reacts with NaOH in water to give 4-hydroxy-3-methylpent-1-ene via the SN2 ...
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Synthesize pivaloyloxymethyl ester, but with a substrate that is a terrible nucleophile
I want to synthesize an pivaloyloxymethyl ester from a fluorophosphonic acid. The idea is, to make a compound cell permeable that than be cleaved in the cell by enzymes. Apparently, the acid is a very ...
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Nucleophilic strength of Fluorine vs iodine
Fluorine is less nucleophilic than iodine because it has greater electronegativity. However, in an aprotic solution, it is more nucleophilic than iodine. Why? I read that fluorine is less stable under ...
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Why do grignard reagents add to carbonyls at the carbonyl carbon, and not deprotonate at the alpha carbon to form an enol? [duplicate]
I thought that since grignards are such strong bases that they would be immediately protonated by the alpha hydrogen since it is an acidic hydrogen. However, I keep seeing answers that are saying that ...
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Why can't ethoxide ion act as nucleophile?
Consider the reaction of chlorocyclohexane with ethoxide in a suitable inert solvent. The major product according to my textbook is cyclohexene, which implies E2 reaction pathway. Why not SN2?
$\ce{...
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Effect of Solvent - Nucleophilicity of RS- and RO-
While reading on order of nucleophilicity of $\ce{RS-}$ and $\ce{RO-}$, I came across this:
Source: Page 355, Organic Chemistry by Jonathan Clayden, Nick Greeves, and Stuart Warren
However, my teacher ...
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Iodide ion is good leaving group and a good nucleophile. How can both be correct?
Leaving Group Tendency of Iodide
$\ce{I-}$ size is big.
$\ce{I-}$ has stable negative charge.
$\implies$ $\ce{I-}$ is good leaving group.
Nucleophilicity of Iodide
$\ce{I-}$ size is big.
$\ce{I-}$...
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What determines strength of nucleophile--Polarisability or Electron density
My understanding is that nucleophiles are lewis bases. Apparently nucleophile and base strength are not the same though. I thought Nu strength/Base strength is determined by how well it can donate an ...
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In hydroboration oxidation reaction .. why do not we use sodium hydroxide alone as a nuclophile?
Why do not we use sodium hydroxide alone as a nuclophile instead of using hydrogen peroxide along with sodium hydroxide
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Why is the reaction rate of tert-butyl chloride solvolysis faster in 80% water/20% acetone, than in 70% water/30% acetone?
The solvent is polar protic, so the mechanism is SN1. However, I don't understand how the composition of water and acetone in the solvent affects the reaction rate.
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Why are cyanamides more electrophilic than nitriles?
According to https://www.researchgate.net/publication/6642597_A_generally_applicable_method_for_assessing_the_electrophilicity_and_reactivity_of_diverse_nitrile-containing_compounds, cyanamides (...
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