Questions tagged [inductive-effect]

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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 ...
12
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2answers
3k 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 ...
5
votes
1answer
321 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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2answers
190 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 ...
4
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1answer
208 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
95 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
172 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 ...
2
votes
1answer
92 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{...
2
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0answers
142 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 ...
2
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0answers
43 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 ...
2
votes
1answer
71 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 ...
1
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1answer
142 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)...
1
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1answer
1k 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}...
1
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1answer
140 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 ...
1
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1answer
34 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 ...
1
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0answers
36 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, ...
1
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0answers
73 views

Problem in defining the Inductive effect

Inductive effect is introduced in many textbooks by giving an example of an alkyl halide $R-X$. The bond C1-X is polar due to electronegativity difference, therefore X gains partial negative charge ∆(-...
1
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0answers
67 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 ...
1
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0answers
433 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 ...
1
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0answers
779 views

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 $\ce{CH3-CH2-NH2}$ was more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ was a stronger +I group than $\ce{CH3}$. ...
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0answers
89 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 ...
1
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1answer
60 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 ...
0
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3answers
76 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 ...
0
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0answers
77 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
49 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 ...
0
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2answers
63 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 ...
0
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0answers
22 views

Comparison between groups with -I effects

So I have a few questions in my book that require me to compare between two different groups on the basis of their -I effects. I have a few questions on this that have been bugging me for quite a ...
0
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0answers
29 views

Trimethylsilyl vs tert-butyl as activating substituent of benzene

Would trimethylsilane as a benzene substituent have an activating effect relative to tert-butyl for electrophilic substitution reactions?
0
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0answers
87 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 $\...
0
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1answer
50 views

Para effects on substituents in aromatic compounds

I wanted to know how to compare the following compounds on basis of acidic strength. I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$. For ...
-1
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1answer
66 views

Why O and N promote SN1 but C=O inhibit SN1 although both are electron-withdrawing?

Source: Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry 2th Edition, 339. The general idea I got so far, is that, carbocation will be more stable if the + charge at central C is ...
-1
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0answers
19 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 ...
-1
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1answer
597 views

Stability order of methy benzyl cations?

I know that meta position shown no resonance effect and hyperconjugation effect . So According to the order given I guess Hyperconjugating effect is taken into account as -CH3 has no Resonance effects....
-1
votes
1answer
394 views

Give the order of nucleophilic addition reaction in the following -

I am confused that whether we should take only inductive or hyperconjugation effect also into consideration while finding the order. As the answer in the book is only according to inductive effect . ...
-1
votes
1answer
63 views

Why is formic acid stronger than acetic acid [duplicate]

Even when acetate ion is stabilized due to resonance why is it a weaker acid than formic acid. It is true that acetic acid has +I effect due to methyl group present on it but resonance is a stronger ...
-2
votes
1answer
1k views

Which Carbocation is most stable among the three? [closed]

According to me the answer should be (C) as that Carbocation will be stablized by resonance with Chlorine. I have read that resonance is the biggest deciding factor about the stability of a ...