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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3answers
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Nucleophilicity in polar aprotic solvent (DMSO)

The strength of a nucleophile in polar aprotic solvent is proportional to its basicity. Lone pair on O- in the molecules will donate an e- pair to an atom. I'm not sure why the alkene ring in 2 makes ...
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0answers
27 views

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-...
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29 views

Formation of isocyanide on reaction with silver cyanide whereas sodium cyanide forms a regular cyanide

Organic halide react with silver cyanide and an isocyanide is formed, whereas on reaction of sodium cyanide, normal cyanide is found. What is the reason behind the difference in the products?? In a ...
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45 views

Nucleophilicity methanol vs water [closed]

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 ...
3
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1answer
37 views

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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76 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 ...
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0answers
191 views

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
415 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 ...
4
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1answer
192 views

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, ...
1
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3answers
567 views

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
41 views

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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0answers
330 views

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
743 views

Which will give faster SN2 reaction

In $\ce{H2C=CH-Br}$ and $\ce{H3C-CH2-Br}$, which will react faster towards a $\mathrm{S_N2}$ reaction? According to me, as double bond exhibit −I effect, hence the 1st should do a faster reaction. Am ...
1
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1answer
561 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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0answers
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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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0answers
54 views

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 ...
13
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2answers
1k 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 ...
9
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2answers
600 views

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
3k views

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 ...
10
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1answer
542 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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3answers
26k 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 ...