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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SN2 on compound containing halogen and carbonyl

I was given the following question on a sample exam for my organic chemistry course: I am quite certain that it would happen in a SN2-type reaction considering that the nucleophile is $\ce{CN-};$ ...
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When does Alcohol act as Solvent and as a Nucleophile?

I was recently solving problems related to Alcohol. and its solution is My doubt is why methanol act as a nucleophile here and when does alcohol acts as a nucleophile and as a Solvent?
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Order of nucleophilicity of ammonia, hydrazine and hydroxylamine

I was reading about nucleophilicity and basic strength orders. I came across this interesting set of three compounds $\ce{NH3},$ $\ce{N2H4}$ and $\ce{NH2OH}$ where I am not able to apply the rules I ...
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Can someone clarify this rationale for using polar, protic solvents in an Sn1?

In the textbook I am reading, it states that an Sn1 mechanism prefers a (polar) protic solvent because the protic solvent helps stabilize the carbocation and solvate the kleavin group, facilitating ...
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Why basicity decreases for leaving groups, but nucleophicity increases for an overall compound, going down the periodic table?

Basically, I read that nucleophilicity increases going down the periodic table within a particular group, due to polarizability, but basicity decreases down a group (or family) in the periodic table, ...
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I'm so confused about the ranking of nucleophilicity please help me!

My instinct is the third one with a minus charge must have biggest nucleophilicity. The second is bigger than first one since lower electronegativity. I guess frist one is less nucleophile than last ...
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Synthesis of Schiff Bases in Aqueous Media

The paper https://www.hindawi.com/journals/jchem/2013/909217/ describes a possibility to synthesize salicylaldehyde-based Schiff Bases using water as a solvent. Yields shown for the microwave-assisted ...
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Which one is the stronger nucleophile? CH3CH2O or CH3CO2 [closed]

Not really sure what the principle would be. Maybe it has something to do with the resonance capability of the two Os in CH3CO2
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Nucleophilicity order of charged and uncharged nucleophile in polar protic solvent

I have read that in polar protic solvents, greater the charge density of a nucleophile, weaker is the nucleophile because of solvent effects. Thus iodide ion is better nulceophile than bromide, ...
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Which is a stronger nucleophile in aprotic solvent: water or hydrogen sulfide? [duplicate]

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 ...
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Order of nucleophilicity of Nitrogen atoms in adenine

I recently stumbled upon a question that got me thinking. It goes something like this: Find the major product of the following reaction: There were 3 options given: So it basically aims at finding ...
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Reactivity of carbonyl derivatives with a nucleophile [duplicate]

As observed, the reactivity of carbonyl derivatives with a nucleophile goes like: Acid halide > acid anhydride > acid > amide > ketone > aldehyde. So is nucleophile a code word to nucleophilic ...
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Source of highly nucleophilic iodide [closed]

What is be the best commercially available source of highly nucleophilic iodide in non-polar solvent? Solvents used are cyclohexane, benzene, chlorobenzene. I can get ahold of bromide quaternary ...
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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 ...
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Why polar aprotic solvents don't surround negatively charged nucleophiles?

Protic solvents can form a tight shell around a nucleophile. But what's stopping any polar solvent from doing so? Shouldn't a polar solvent surround negatively charged $\ce{F-}$ with its partially ...
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Bromination of an alkene in presence of water

Bromination of an alkene in presence of water results in its mechanism in a cyclic bromonium ion and "afterwards $\ce{H2O}$ binds to the carbon atom surrounded by more electron donating groups." This ...
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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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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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427 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 ...
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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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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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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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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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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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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 ...
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991 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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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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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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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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Effects of Groups on the Nucleophilcity of Nitrogen

The reactivity of nitrogen mustards increases with increasing nucleophilicity of the central nitrogen atom. Select the most and least reactive from each of the following groups of nitrogen mustards. ...
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Ranking order of nucleophilicity

According to me the answer should be (c),(b),(a),(d). As we move left to right in a period the electronegativity increases and hence the tendency to donate electrons will decrease so nitrogen is ...
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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 ...
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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 ...