Skip to main content

Questions tagged [inductive-effect]

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

Filter by
Sorted by
Tagged with
1 vote
2 answers
473 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 ...
0 votes
0 answers
55 views

what role does mesomeric effect and inductive effect play in stability of carbocations in presence of halogens

what should be the ideal explanation behind the order of stability of these three compounds? Case-1 In these three examples the first two structures have a positive mesomeric effect and it is greater ...
1 vote
0 answers
3k views

How come the methyl group (-CH3) is electron donating?

If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
-2 votes
2 answers
58 views

Stability of phenylic carbocations [closed]

Problem: Structure (1) is more stable than structure (2). My teacher stated that Structure (1) is more stable than Structure (2). I find this confusing. How can Structure (1) be more stable when ...
1 vote
1 answer
197 views

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 ...
3 votes
1 answer
118 views

If a compound has a strong and weak minus I group, will the stronger group always have a δ- charge?

In a compound like acrolein (prop-2-enal or $\ce{CH2=CH-CHO}$, will the oxygen in the $\ce{-CHO}$ group always have a $\delta$- charge? Acrolein does have three resonance structures as shown below, ...
-1 votes
1 answer
98 views

Inductive Effect (R-NH3+ and R-NH2)

Textbooks I've read state that R-NH3+ has exhibits a greater -I inductive effect than R-NH2 does. However, I've also read in places that the + charge in R-NH3+ only represents a formal charge and has ...
46 votes
2 answers
26k 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 ...
0 votes
1 answer
237 views

Can alkyl groups show -I effect?

Inductive effect is the partial shifting of the sigma-bonding electrons towards more EN (take as electronegativity or electronegative in this text) atom so why we will say that alkyl groups will ...
3 votes
1 answer
4k views

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 ...
-3 votes
1 answer
114 views

+M or -I for chlorine? Major product in free radical chlorination and bromination of 2-chloropropane?

Is the +M or -I effect more dominant in when an alkyl (mono)halide is subject to free radical chlorination/bromination? For example what will be the major product in case of free radical (mono)...
-1 votes
1 answer
435 views

Why is the melting point of 4-bromoacetanilide so high? Does it have any reason to do with the chemical structure, or the para aspect?

We used melting point to determine the type of bromoacetanilide, and it was closest to 4-bromoacetanilide. How can I explain why the melting point was what it is?
4 votes
2 answers
919 views

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 ...
-2 votes
1 answer
86 views

Acidic strength order among hydroxytetralones [closed]

I can understand in 1 the conjugate base has more stability for better resonance but in 2 and 3 the effect of resonance cannot be considered. How can we compare the inductive effect in such case?
1 vote
0 answers
855 views

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 ...
1 vote
1 answer
579 views

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 ...
4 votes
2 answers
5k views

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 ...
2 votes
1 answer
2k views

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, ...
3 votes
0 answers
102 views

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 ...
1 vote
0 answers
293 views

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-...
3 votes
0 answers
511 views

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, ...
2 votes
1 answer
173 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 $\...
1 vote
1 answer
2k views

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-...
3 votes
0 answers
3k views

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 ...
1 vote
1 answer
863 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 ...
1 vote
0 answers
103 views

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 ...
12 votes
2 answers
2k 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-...
-1 votes
1 answer
152 views

Reactivity of Alkenes with HBr [closed]

I am new in the Organic Chemistry (World of Reactions). I had got one question in my test. But, when I had seen it, I got no proper logic to tick the correct answer, and then when I saw solution, then ...
0 votes
1 answer
2k views

Inductive Effect of -CH3 group [duplicate]

3° carbocations are the most stable because of the +I effect of -CH3 group. This group gives a slight negative charge to the central carbon atom, which makes it less positively charged and thus, more ...
0 votes
0 answers
317 views

Why does chlorine show a mesomeric effect in haloarenes and an inductive effect in haloalkanes?

Chlorine shows the +R effect in haloarenes and the -I effect in haloalkanes. Does chlorine do the same for all cyclic compounds or only for aromatic rings? Is this just another experimentally seen ...
2 votes
0 answers
643 views

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 ...
1 vote
0 answers
30 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 ...
0 votes
0 answers
1k 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 ...
2 votes
0 answers
90 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 ...
4 votes
1 answer
299 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 ...
0 votes
0 answers
49 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 ...
2 votes
1 answer
860 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 votes
1 answer
639 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 ...
3 votes
1 answer
887 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'...
8 votes
2 answers
389 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 $\ce{-\overset{+}{N}R3}$ ...
1 vote
1 answer
128 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 ...
1 vote
0 answers
62 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 $\...
0 votes
1 answer
2k 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 ...
4 votes
2 answers
351 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 ...
3 votes
1 answer
150 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 ...
2 votes
0 answers
194 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 ...
-3 votes
1 answer
141 views

Confusion in comparing the contribution of resonating structures to resonance hybrid [closed]

So I was comparing the $+M$ effect of $\ce{-CH^-_2}$, $\ce{-NH^-}$ and $\ce{-O^-}$. Answer was given as: $$ \ce{-CH^-2 > -NH^- > -O^-}$$ So, I attach them with ethene and made their respective ...
3 votes
1 answer
177 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 ...
0 votes
0 answers
77 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 $\...
1 vote
0 answers
3k 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 $\ce{CH3-CH2-NH2}$ is more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ is a stronger +I group than $\ce{CH3}$. ...