Questions tagged [inductive-effect]
Use for questions regarding the so called inductive effect of substituents on properties of compounds.
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Inductive effect of hydrogen isotopes
Why does the electron-donating inductive effect (+I) of the isotopes of hydrogen decrease in the order $\ce{T} > \ce{D} > \ce{H}$?
(where T is Tritium and D is Deuterium)
Google has nothing to ...
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When 2-pentene reacts with HBr, what will be the major product?
If we consider the first step (formation of carbocation by the attack of the proton).
A couple of textbooks I referred say that when the substituents on the $\ce{C=C}$ are different, the direction of ...
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Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?
If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows:
Even after deprotonation, it has intramolecular hydrogen bonding as follows:
My question:
p-...
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How do steric effects affect inductive effect in compounds with tetravalent nitrogen?
I want to compare the electron density on methyl group between tri‐tert‐butyl(methyl)azanium (1) and triisopropyl(methyl)azanium (2), i.e. essentially the inductive effects of $\ce{-\overset{+}{N}R3}$ ...
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Effect of phenyl and vinyl substituents on Acidity of carboxylic
Recently I came across this statement in my textbook:
Direct attachment of groups such as phenyl or vinyl to the carboxylic
acid, increases the acidity of corresponding carboxylic acid contrary
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Which of the two structures is more stable?
Which of the two structures is more stable?
As far as I know, alkenes with a greater number of hyperconjugating structures are more stable. Hyperconjugation has a greater stabilizing effect than ...
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Acidic strength of nitrophenols
I've seen the pKa values of Nitrophenol as follows:-
pKa of o-nitrophenol= 7.23
pKa of p-nitrohenol= 7.14
so p-nitrophenol is more acidic than p-nitrophenol
But both phenoxide ions are stabilized ...
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Why don't we consider the attached hydrogens in inductive effect?
Consider the molecule 1-chloroethane
Let carbon attached to $\ce{Cl}$ be $\ce{C1}$ and other one be $\ce{C2}$. While learning inductive effect I was told that $\ce{Cl}$ due to high electronegativity ...
user108965
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What does acidity of para-alkyl substituted phenols depend on?
Problem
Arrange the following organic compounds in decreasing order of acidity.
Answer
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According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
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Does Cl- Have more -I effect or +M effect ( Resonance effect)?
In this question my answer was (A) because I thought $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$. But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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Effect of electronegative groups and length of alkyl chain on inductive effect among carboxylic acids
According to my teacher, the inductive effect in $\ce{CH3COOH}$ exists because of the electron deficiency on $\ce{C}$ (partial positive charge $\delta +$) as a result of the electronegativity of the ...
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Stability of meta ethyl and meta methyl benzene carbocations respectively
It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
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Relative acidity of acetic acid derivatives with strongly withdrawing substituents
What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following:
$\ce{O2N-CH2-CO2H},$
$\ce{Me3\overset{+}{N}-CH2-CO2H},$
$\ce{NC-CH2-CO2H},$
$\ce{HO-CH2-CO2H}?$
Since only the groups ...
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Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?
Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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Stabilization of multiple bonds through inductive effects
In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
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Inductive effect of alkyl ammonium groups
Why $\ce{-NR3+}$ has more -I effect than $\ce{-NH3+}?$
And what about order of $\ce{-NHR2+}$ and $\ce{-NH2R+}?$
My attempts
I got idea about electronegativity of carbon atom in $\ce{R}$ is more than ...
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Does hyperconjugation into sigma-star explain methylamine's increased basicity relative to ammonia?
The inductive effect with the polarisation of the C-N bond obviously plays a role in stabilising the positive charge of the conjugate acid. But given the similar electronegativities for C and H, CH3 ...
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Is Bent's Rule an alternative explanation for the Inductive Effect?
Today I read that Bent's Rule can be used to explain the inductive effect (I was reading the Consequences section of this Wikipedia article). If I understand it correctly, for a molecule CL3R, the ...
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How to establish trend of carboxylic acid acidity in the presence of certain substituents?
I encountered a question in my textbook which asked the following:
At first, i thought that i can approach it in the same way i sort the effect of EDG and EWG on the acidity of phenols, that is, ...
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Which substitutent should be placed on axial position in SCl2(OCH3)2?
According to Bent's rule, in $\mathrm{sp^3d}$ more electronegative element is placed on the axial position, so between $\ce{Cl}$ and $\ce{OCH3}$ in $\ce{SCl2(OCH3)2}$ which should be placed on axial ...
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Stability of carbocation directly attached to a halogen atom [duplicate]
I have two compounds..
How is the first one more stable?
As I have been taught that -I effect of Chlorine dominates its +R effect but to explain this case, My teacher is saying that because of the ...
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Is NH2 electron donating or electron withdrawing? [closed]
Can anyone explain why NH2 shows -I in inductive effect and +R in resonance effect? I mean NH2 is ready to take electrons in inductive effect (with its electronegativity) but in the resonance effect, ...
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Why is ethanol more acidic than acetone?
The acidity of a compound is determined by the stability of its conjugate base and the major structure of enolate has a negative charge on the Oxygen atom. Moreover, the negative charge on the O-atom ...
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Effect of distance on the mesomeric effect
I have always thought that mesomeric effect is somewhat dependent on distance.
But I recently came across a question where I was asked to predict the order of stability of o-methoxyphenyl carbocation ...
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Change in inductive effect of a susbstituent when -R group replaces -H atom
There are several examples where the negative inductive effect of a substituent gets increased when a hydrogen atom on that substituent is replaced by an alkyl group.
Some particular examples:
$$\ce{...
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Order of −I effect among ethenyl and 1-propenyl groups
We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power?
The $\...
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What is the correct order of Relative Inductive Effect (-I) of different groups?
This confusion has put me in problem several times since last 2 years and I have been looking for a clarification but it seems that answer depends upon who you ask. I have several examples where I ...
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Difference between nucleophilicity of phenoxide ion and acetate anion in protic/aprotic solvent
As far as I could think, the phenoxide ion is comparatively larger as compared to acetate ion, so it should undergo less solvation in presence of a protic solvent and thus its nucleophilicty should be ...
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Hydrogen as a reference in inductive effect
What does it mean when we say that I-effect of hydrogen is taken as zero ?
I think that it means that partial displacement of sigma bond electrons between two atoms of different electronegativity is ...
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Why does the carboxylate ion show positive inductive effect?
While solving some problems on general organic chemistry, I came across this question that asked for the nature of inductive effects of $\ce{-CH_3}, \ce{-CO_2^-}, \ce{-Br}, \ce{-NH_3^+}$.
And in the ...
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Comparison of basicity of Aniline, p-Anisidine, and o-Anisidine [duplicate]
I have a question where I am required to compare the basicity of Aniline, o-Anisidine, and p-Anisidine.
Now here's what I do know:-
In ortho substituted aniline, an ortho effect acts which reduces ...
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Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?
Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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Why is the inductive effect possible?
Firstly, I must preface that I am a Biology student. To elaborate my question, I was looking for the reason why carboxylic acids are more acidic than alcohols, despite both compounds containing —OH ...
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Effect of electron-donating and electron-withdrawing groups on the C=O bond
My notes states this:
An electronegative element tends to draw in the electrons between the carbon and oxygen atoms through its electron-withdrawing effect. This strengthens the C=O bond.
An electron-...
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What is the stability order of the carbocation and carboanion?
So I came up with examples as below:
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2
Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
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Carbocation formation and stability from bromo compounds
When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
This is my ...
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Comparing relative negative inductive effect of substituents (dialkyl amine, amine, alkoxide, fluoride)
Which of the following is correct with respect to the negative inductive effect of the substituents?
1. $\ce{-NR2 < -OR < -F}$
2. $\ce{-NH2 < -OR < -F}$
3. $\ce{-NR2 > -OR > -F}...
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How to explain regioselectivity in nucleophilic aromatic substitution
I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide:
I have predicted that the para-substituted product is formed as ...
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Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?
I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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Inductive effect of -NHMe
Why does $\ce{-NHMe}$ show -I effect. I think it should be opposite. I know that $\ce{-Me}$ groups are electron donating in nature. So the nitrogen atom will have a small $\delta^-$ charge. So then ...
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Confusions about inductive effect and acid strength
If one of the hydrogens in the alkyl side chain of ethanoic acid is replaced with an atom of Chlorine, the acid has a larger Ka value. My book says this is since the Cl "borrows" electron density from ...
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Is there a quantitative definition of inductive effect?
Usually, Inductive effects are compared using the electronegativities and distances. However, this only works in compounds with similar structures. For example, we can predict the following orders of ...
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Effect of beta branching and carbocation rearrangement on SN1 reaction rates
My book (NCERT class 12 Chemistry) asks
Predict the order of reactivity of the four isomeric bromobutanes in SN1 and SN2 reactions.
The answer given for SN1 is
1-bromobutane < 1-bromo-2-...
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Comparing acidic strength of acetic and p-anisic acids
In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
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Does inductive effect operate through pi bonds?
I have been told that the inductive effect is only present in sigma bonds by my teacher, and the book I've referenced also says the same thing.
However, I can't think of why this is. Answers to this ...
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Ortho effect and the relative acidity in aromatic acids [duplicate]
What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid?
I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
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Evaluating inductive effects in cyclic compounds
I was required to find the products on heating the hydroxide of;
Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
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Methyl group and acidic nature [duplicate]
After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
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How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?
I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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Which of the following groups show +M and -I effect?
Which of the following group show +M and -I effect?
(A) $\ce{-\underset{\underset{\huge O}{||}}{C}-F}$
(B) $\ce{-\underset{\underset{\huge O}{||}}{C}-OR}$
(C) $\ce{-O^-}$
(D) $\ce{-OH}$
Answer is ...
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