Applied to a chemical species, the term expresses a thermodynamic property in reference to a standard, stating that one state is lower in energy than another. The tag should be applied to questions seeking answers with respect to the stability (or instability) of a certain chemical species, ...

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Stability between cyclopentdiene compound

What will be the order of stability? According the me it should be : Cyclopentadienyl anion > Cyclopentadiene > Cyclopentadienyl cation because the order of stability is aromatic > non-aromatic ...
1
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1answer
34 views

Predicting major product of a reaction with nitrous acid

$\hspace{4.5cm}$ For the above reaction I am asked to predict $\ce{X}$, the major product. Of the options given, I thought product (1) would be correct, seeing as how it has the most stable ...
1
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0answers
24 views

Advantage of using sodium sulbactam over sulbactam

Part of the question reads: "and explain why it is advantageous to produce the compound as its sodium salt rather than in the carboxylic acid form." My thinking is that the carboxylate can resonance ...
2
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1answer
148 views

Is the phenyl cation or ethynylium more stable?

I recently gave an exam and I received an interesting question to which I believe the answer is wrong. Given two compounds, a benzene molecule with carbocation at one of its constituting carbon atoms ...
6
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1answer
106 views

Why are bromine oxyanions uncommon?

Sodium hypochlorite is used in bleach, calcium hypochlorite is used in public swimming pools, ammonium perchlorate is used in solid rocket fuel. Sodium periodate is used in the cleaving of ...
1
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0answers
31 views

What is the most stable oxide of Fr?

I read that the heavier alkali metals, like K, Rb, and Cs all prefer to form superoxides. Since Fr is the heaviest alkali metal, I assumed it would follow the same trend as the previous alkali metals, ...
2
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1answer
63 views

Confusion with Cannizzaro reaction?

In the given mechanism, is it okay to prefer hydrogen as a better leaving group than the formyl group? The negative charge on an sp2 hybridized carbon, with carbonyl attached to it seems to be more ...
1
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1answer
104 views

Why are anti aromatic compounds unstable?

Just like aromatic compounds, anti aromatic compounds have several resonance structures and some of them are also conjugated ( 1,3-cyclobutene). Why is it that just having 4n electrons makes them ...
5
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1answer
84 views

Why is WF6 more likely to be formed over CrF6?

We know that $\ce{F-}$ is going to be a hard base since it is small and relatively polarizable. Both $\ce{Cr^6+}$ and $\ce{W^6+}$ are hard acids, but shouldn't $\ce{CrF6}$ be favored since it would ...
4
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0answers
66 views

How are SN2 transition states stabilised by adjacent double bonds and carbonyl groups?

It is my understanding that transition states in an SN2 reaction have some filled and some empty orbital character, as we have the backside of the C-X σ* beginning to fill with electrons from the HOMO ...
3
votes
1answer
151 views

Why are 7-membered rings less likely to form than 5- and 6- membered rings?

Google did not give me any useful reference for that nor has this question been asked before at SE:Chemistry. I see 5- and 6-membered ring products as the major products even when 7-membered rings ...
0
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1answer
44 views

Why only the unstable resonating structure proceeds in the reaction?

For example, in the given image, I have starred the step where the relatively unstable resonating structure proceeds forward in the reaction. Why?
4
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0answers
56 views

Stability between Tropylium and Tri cyclopropyl methyl carbocation

Why is Tropylium less stable than Tri cyclopropyl methyl carbocation? Tri cyclopropyl methyl carbocation undergoes sigma-tropic rearrangement whereas Tropylium is highly stable due to conjugated ...
1
vote
1answer
49 views

Confusion in finding electrophilic centre

In the compound CH3-CH2-CN the electrophilic centre according to my NCERT TEXTBOOK(class 11) is the carbon of cyanide but I think it should be the the carbon adjacent to cyanide since, during bond ...
7
votes
3answers
290 views

Is there any possibility of tautomerisation to en-ol form?

In the picture, you can see the bridge whose end points are in para relation (for making the image clear). Now, what my friend said is that there is no possibility of tautomerisation as there is no ...
1
vote
0answers
34 views

Thermodynamic control or kinetic control?

In my notes, it is written that the case 1 product will be major one. The explanation given is as follows:- However, since the pi clouds of alkenes are perpendicular to each other, the resonance ...
3
votes
2answers
81 views

Why is the hypoiodite anion unstable in solution, whereas hypochlorite is relatively stable?

$\ce{Cl2}$ and $\ce{Br2}$ can disproportionate in a cold, aqueous, basic environment to form $\ce{ClO-}$ and $\ce{BrO-}$ respectively, yet $\ce{I2}$ directly forms $\ce{IO3^-}$. Why isn't $\ce{IO-}$ ...
6
votes
1answer
62 views

Why is ICl5 unstable?

For the question Why is $\ce{ICl5}$ unstable? my textbook gave an answer of $\ce{ICl5}$ has too many highly electronegative chlorine atoms present on the central iodine. But how does ...
11
votes
2answers
342 views

Why quaternary nitrogen but not tertiary oxygen?

Why do quaternary ammonium ions with a partially positive nitrogen form fairly readily and are often stable but tertiary oxygens, apparently called oxonium ions, are more rare/less stable? The trend ...
4
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0answers
32 views

Can 0-Carborane be stored at room temperature?

I am a physics post-doc at Oak Ridge National Lab (with a bit more training in chem than the average physicist). I ordered a small sample of o-Carborane from Sigma-Aldrich to test for doping liquid ...
2
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1answer
66 views

I am confused about the stability of carbanion III and IV in the image

I am confused about the stability of carbanion III and IV in the image, I think III is more unstable because of electron donating effect (+R) of -OCH3 group but my book says III is more stable than ...
1
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1answer
70 views

Dependence of carbocation stability with respect to the length of alkyl group

Which carbocation is more stable, the ethyl carbocation or n-propyl carbocation? What is the effect of alkyl group length on the stability of a carbocation?
3
votes
0answers
58 views

Why doesn't H-O-O-O-O-O-O-O-O-H exist? [duplicate]

The question has its roots in why only carbon mainly shows catenation. I don't see why such a compound cannot be formed. Why don't we have a whole branch dealing with such compounds other than organic ...
0
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1answer
142 views

Stability of the phenoxide ion

The phenoxide ion is more stable than the phenol itself because of its more stabilized resonance structures. On the other hand, however, we say phenoxide ions are more susceptible to electrophilic ...
1
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1answer
126 views

Nitrogen molecule vs carbon-carbon triple bond stability

Why does the triple bond in the nitrogen molecule convey stability, whereas a triple bond between carbon atoms conveys instability?
4
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3answers
196 views

Which tautomer of hexane-2,4-dione is more stable?

Which tautomer will be more stable? Both 1 and 2 show intramolecular hydrogen bonding and form 6 membered cyclic ring, thus increasing the stability. I think I need to compare the effect of the ...
8
votes
2answers
206 views

Why is the eclipsed conformer more stable than the bisected conformer in 1-butene?

I have just started learning conformational analysis, and a major doubt came into my mind. In simple alkanes such as ethane, the staggered conformer is much more stable than the eclipsed conformer. ...
1
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1answer
40 views

Is Tollen's test safe?

Tollen's test is an important test to distinguish between aldehyde and ketone. $$\ce{2 [Ag(NH3)2]+ + RCHO + H2O → 2 Ag(s) + 4 NH3 + RCO2H + 2 H+}$$ But is this reaction safe? Is there any threat in ...
0
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0answers
75 views

What is the order of stability of the following carbocations?

Here's my attempt: So clearly the first 2 are more stable than the last 2 as they involve resonance in ring i.e. the mesomeric effect. Also as the 1st one has a bigger carbon group attached to it ...
0
votes
1answer
106 views

Which complexes are stable: ammine complexes or carbonyl complexes?

According to Wikipedia, A spectrochemical series is a list of ligands ordered on ligand strength and a list of metal ions based on oxidation number, group and its identity. $$\ce{I- < ...
7
votes
2answers
244 views

Why Cu+ is unstable in aqueous medium?

This was one of the question that was given in the school exam. But what I am expecting is that $\ce{Cu+}$ attains a $d^{10}$ configuration by losing one electron from s-subshell. Since it has fully ...
4
votes
1answer
226 views

Order of reactivity of carbonyl compounds towards nucleophilic addition

Arrange the following according to reactivity towards nucleophilic addition reaction: I have already seen this post regarding the reactivity. It helped me to some extent. $\ce{Cl}$ increases ...
8
votes
1answer
525 views

Why is sulfur hexafluoride highly stable?

I was just reading about p Block elements from two different books. Both books say that $\ce{SF6}$ is extremely stable in 16th group due to steric reasons but my question is why is it more stable than ...
4
votes
1answer
57 views

Stability of alkenes by hyper conjugation

I have learnt that for carbocations, electrons are delocalized from the $\ce{C-H}$ $\sigma$-bond to the empty p-orbital of carbon. Moreover, alkenes are stabilized by the delocalization of electron ...
8
votes
3answers
172 views

Why is diene more reactive than alkene?

The chemical reduction of 1,3-butadiene with sodium in alcohol gives mainly the 1,4-addition product that is but-2-ene. Under these condition the isolated double bond are not reduced. This suggest ...
11
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1answer
181 views

Stability of isomers of N4O

I have googled and found that the structure of $\ce{N4O}$ is linear with a positive and negative charge on 2 nitrogen atoms. But, the following structure seems more stable because it fulfils octet for ...
1
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0answers
20 views

Can there be gaps in autoignition temperatures?

I recently saw a request for solids that auto-ignite between 80C and 160C. I can't find any, and none have yet been suggested. Which leads me to the theoretical question: Is it possible for there to ...
1
vote
1answer
85 views

Why does Iodine form Cations sometimes?

It is reported that iodine forms compounds like $\ce{(CH3COO)3I}$, $\ce{I(ClO4)3}$ and $\ce{IPO4}$ which contains $\ce{I+}$ and $\ce{I^3+}$ and are not bonded covalently as in interhalogen compounds. ...
3
votes
1answer
72 views

What is meant by 'stability'?

I'm currently learning about substitution and elimination reactions and to do so I need to learn about bases and nucleophiles. Apparently a good base is an unstable species. What does stability ...
1
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1answer
69 views

Stability of carbocations

We know that if a structure has all equivalent resonance structures, then it will be highly stabilised. So then why benzylic carbocation is more stable than other cyclic allylic carbocations, though ...
2
votes
2answers
2k views

Is iron the most stable element in the periodic table?

According to the binding energy per nucleon vs mass number graph, it is observed that iron-56 has the maximum value of binding energy per nucleon (8.75 MeV).It means that Iron-56 is the most ...
11
votes
1answer
343 views

Stability of carbocations: CF3+ vs CH3+

Is $\ce{CF_3+}$ more stable than $\ce{CH_3+}$? In $\ce{CF_3+}$, there is $\ce{C-F}$ back bonding that increases stability of the carbocations. But -I effect of $\ce{F}$ dominates +R effect and this ...
3
votes
0answers
58 views

Influence of neighboring fluorine and hydroxyl on carbocation

Which of the 2-fluorobutan-3-yl and butan-2-ol-3-yl carbocations will be more stable? I know that fluorine has a greater electron-withdrawing inductive effect, but what about the resonance effect of ...
0
votes
1answer
105 views

Why are phosphate-phosphate bonds weaker than phosphate-water bonds?

According to the Wikipedia entry on ATP, ATP is an unstable molecule in unbuffered water, in which it hydrolyses to ADP and phosphate. This is because the strength of the bonds between the ...
2
votes
0answers
30 views

order compounds based of increasing heat of combustion

order compounds based of increasing heat of combustion (least is 1, most is 4) Could someone tell me if my answers are correct? For A) I went off that equatorial bonds are more stable (less ...
6
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1answer
253 views

Why are aromatic compounds so stable?

I've never actually been told deeper reasons for this. In organic chemistry classes (1 and 2) we're usually told that aromatic compounds are very stable whereas anti-aromatic ones are not, and also, ...
3
votes
1answer
601 views

Stability of furanose vs. pyranose form of glucose?

I am trying to imagine the cyclization of the Fischer projection of glucose as it forms an $\unicode[Times]{x3B1}$-D-glucofuranose and an $\unicode[Times]{x3B1}$-D-glucopyranose (right now I am trying ...
3
votes
1answer
51 views

Do hydrogen peroxide stabilizers affect oxidizing ability

I plan to use hydrogen peroxide for a redox reaction in oxidizing $\ce{I-}$ to $\ce{I}$. I found 20 volume hydrogen peroxide as a hair developer, but it contains stabilizer. I imagined these would ...
15
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2answers
744 views

Which of the following is the more stable carbocation?

Which of the following is the more stable carbocation? I thought the 1st carbocation would be the more stable one as the pi-electron density of phenyl group can overlap with the vacant orbital on ...
2
votes
1answer
137 views

Confused about carbocation stability

For which element 'X' is the carbocation $\ce{CH3-X-CH2+}$ the most stable? A. X = S B. X = N C. X = O I thought since oxygen is the most electronegative among the options, it would create the ...