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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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Nucleophilic nature of ions

Consider the following species: $$ \underset{(\text{A})}{\ce{\overset{⊖}{O}H}} \quad \underset{(\text{B})}{\ce{CH3-\overset{⊖}{O}}} \quad \underset{(\text{C})}{\ce{\overset{⊖}{C}H3}} \quad \...
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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 ...
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Better nucleophile OH- aur OCH3- in aqueous medium

Which of the two, Hydroxide anion OH- and Methoxide ion OCH3-, is a better nucleophile in aqueous medium?? I have 2 arguments both against each other. First, Oxygen atom in methoxide has higher ...
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2answers
178 views

Order of Nucleophilicity

I know this question has been asked many times but I need to confirm this doubt which has been pestering me for the past few days. Suppose in an $\mathrm{S_N2}$ reaction (in polar aprotic solvent) we ...
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1answer
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Why is fluoride the most nucleophilic halide in aprotic solvents? [duplicate]

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents. From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, ...
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3answers
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Why does using NaI as a nucleophile and acetone as solvent lead to an SN2 reaction mechanism instead of SN1? Is I- not considered a weak nucleophile?

In a reaction with a secondary leaving group, why does using $\ce{NaI}$ with acetone as a solvent lead to an $\mathrm{S_N2}$ reaction mechanism instead of $\mathrm{S_N1}$? I thought that halogens were ...
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1answer
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Difference in leaving group ability due to variation in nucleophiles

Wikipedia writes: There can still exist contextual differences in leaving group ability in the purest form, that is when the actual group that leaves is not affected by the reaction conditions (by ...
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Electrophilic addition of IBr to alkene

I would assume options A and B are possible products due to the $\ce{I+}$ electrophile attacking the alkene, and hence are ruled out. However, I am torn between options C and D. Both products are ...
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2answers
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Which will give faster Sn2 reaction

In $\ce{H2C=CH-Br}$ and $\ce{H3C-CH2-Br}$, which will react faster towards a SN2 reaction? According to me, as double bond exhibit -I effect, hence the 1st should do a faster reaction. Am I right or ...
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1answer
454 views

Nucleophiles in protic and aprotic solvent [closed]

If the nucleophiles have almost same size (not a large difference) such as $\ce{C- , N- , O-}$ then how their nucleophilicty varies in protic and aprotic solvents?\ Does it depend on types of ...
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Nucleophilicity of halides in solvents [duplicate]

I have studied that as electronegativity increases nucleophilicity decreases. But in the aprotic solvent the order of nucleophilicty is: $$\ce{F- > Cl- > Br- > I-}$$ but how is this possible ...
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How can a weak base act as a strong nucleophile (and vice versa)?

Carboxylate ion ($\ce{RCOO-}$) is a weak base as the negative charge on oxygen is delocalised due to resonance. So, it has less tendency to donate lone pair of electrons to H+ ion. Similarly, it has ...
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2answers
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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 ...
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2answers
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Which is a better nucleophile: hydroxide anion or amide anion?

I know that nucleophilicity order depends on what type of solvent we take, polar protic or polar aprotic and also on the basicity of nucleophile. In DMF, which is a better nucleophile $\ce{NH2-}$ ...
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4answers
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How to determine the order of nucleophilicity for given chemical species?

How to determine the order of nucleophilicity for given chemical species? Like I came across this question, to rearrange $\ce{RCOO-, OR-, OH-, H2O}$ (alkyl acetate, alkoxide, hydroxide, and water) in ...
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1answer
491 views

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 ...
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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 ...