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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1answer
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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
\...
0
votes
0answers
40 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 ...
0
votes
0answers
34 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 ...
1
vote
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 ...
4
votes
1answer
99 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, ...
0
votes
3answers
162 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 ...
0
votes
1answer
36 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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votes
0answers
250 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 ...
0
votes
2answers
491 views
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 ...
1
vote
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 ...
3
votes
0answers
82 views
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 ...
1
vote
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
votes
2answers
909 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
votes
2answers
504 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 $\ce{NH2-}$ ...
2
votes
4answers
2k 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
votes
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 ...
5
votes
3answers
25k 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 ...
