Questions tagged [inductive-effect]

Use for questions regarding the so called inductive effect of substituents on properties of compounds.

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43
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19k views

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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2answers
7k views

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 ...
11
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2answers
224 views

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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2answers
217 views

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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2answers
142 views

What does acidity of para-alkyl substituted phenols depend on?

Problem Arrange the following organic compounds in decreasing order of acidity. Answer Question 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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1answer
1k views

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 ...
4
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1answer
258 views

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 ...
3
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1answer
66 views

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'...
3
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1answer
102 views

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 ...
3
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1answer
1k views

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 ...
3
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1answer
127 views

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 ...
3
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1answer
152 views

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 ...
3
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1answer
346 views

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 ...
3
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1answer
296 views

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 ...
2
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1answer
159 views

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 ...
2
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1answer
69 views

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 ...
2
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1answer
76 views

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 ...
2
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1answer
223 views

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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0answers
34 views

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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0answers
62 views

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 ...
2
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1answer
70 views

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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0answers
422 views

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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0answers
179 views

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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0answers
45 views

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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1answer
199 views

What is the stability order of the carbocation and carboanion?

So I came up with examples as below: 1 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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1answer
44 views

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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1answer
2k views

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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1answer
95 views

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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2answers
2k views

Does Cl- Have more -I effect or +M effect ( Resonance effect)?

In this question my answer was (A) because i though $\ce{NH2}$ 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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1answer
85 views

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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1answer
173 views

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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0answers
15 views

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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0answers
40 views

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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1answer
147 views

Inductive effect vs electronegativity [closed]

Why is the inductive effect of chlorine, bromine, and iodine stronger than that of hydroxy group, even though oxygen is more electronegative?
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1answer
209 views

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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0answers
49 views

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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0answers
139 views

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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0answers
1k views

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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0answers
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Why is C2H5 a stronger +I group than CH3?

While reading about the basic character of amines, I came across a note which said that $\ce{CH3-CH2-NH2}$ is more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ is a stronger +I group than $\ce{CH3}$. ...
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0answers
103 views

Mechanism of substitution for disubstituted benzene

Here, I count the individual effects of the two oppositely directing groups. I assume that the deactivation of $\ce{NO_2}$ group at ortho and meta positions is higher. While bromination, I get the ...
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1answer
250 views

The most acidic hydrogen among ethane, ethene, ethyne and allene

Among $$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$ I need to find out the one having highest acidic hydrogen. As per my observations, there are two equivalent resonating ...
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3answers
188 views

Odd looking carbocation stability order [duplicate]

I am studying introductory organic chemistry, suddenly this one started looking odd, The carbocation stability for three compounds as given by my book is shown below, Let me call those as ...
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1answer
111 views

Acidic nature comparison; benzoic acid and phenylacetic acid

The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively. In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
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1answer
252 views

Estimation of dipole moments in aromatic compounds

If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both? E.g. we have to compare dipole moment in pyrrole and furan then in ...
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0answers
40 views

Why is the carbanion stability order the way it is? (3*<2*<1*)

According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help) With my very ...
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0answers
39 views

Comparing nucleophilic strengths of tetrahydropyran and (2R,6R)-2,6 dimethyltetrahydropyran

Compare the nucleophilic strengths of the following two compounds: According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I ...
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0answers
45 views

Combined Effect of Steric Inhibition of Resonance and Inductive Effect

While qualitatively comparing the acidic nature of o-methyl benzoic acid and benzoic acid, we consider the steric effect due to which the $\ce{-COOH}$ group loses its planarity and the +M effect of $\...
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0answers
121 views

Inductive effect of acetyl group

Question: Since the acetyl group provides $-M$, methyl $+I$ and chlorine $-I$, it is obvious that the correct order is as given in option $(a)$ However while solving such questions I would compare ...
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0answers
211 views

Does the electron displacement effect act only on sigma electrons?

Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be. I reasoned it can not affect the pi ...
0
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1answer
397 views

Carbanion Stability order [duplicate]

Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...