Timeline for Oxygen or carbon with a positive charge? (comparison of canonical structures)
Current License: CC BY-SA 4.0
20 events
| when toggle format | what | by | license | comment | |
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| Feb 6, 2020 at 16:40 | history | edited | Karsten♦ | CC BY-SA 4.0 |
added 50 characters in body; edited title
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| May 23, 2018 at 7:50 | answer | added | james | timeline score: -1 | |
| Oct 9, 2017 at 2:56 | answer | added | Mike | timeline score: 2 | |
| May 24, 2017 at 5:19 | comment | added | Pritt says Reinstate Monica | Octet is not complete for carbon in (A). Option (B) is more stable with more octet satisfying atoms, | |
| Aug 15, 2014 at 3:51 | answer | added | Caters | timeline score: -2 | |
| Mar 2, 2014 at 11:03 | vote | accept | mikhailcazi | ||
| Oct 29, 2013 at 11:10 | answer | added | Ben Norris | timeline score: 13 | |
| Oct 29, 2013 at 10:13 | history | edited | mikhailcazi | CC BY-SA 3.0 |
added 309 characters in body
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| Oct 29, 2013 at 10:09 | comment | added | mikhailcazi | @SatwikPasani okay, so option (B) is more stable because 1) extra bond 2) carbon octet complete. Thanks! This helped. | |
| Oct 28, 2013 at 20:13 | comment | added | LordStryker | @SatwikPasani Just for the sake of thoroughness, an oxygen pulls more electron density toward itself, not actual electrons themselves. | |
| Oct 28, 2013 at 18:50 | answer | added | William Everett | timeline score: 2 | |
| Oct 26, 2013 at 13:56 | comment | added | stochastic13 | @mikhailcazi in general, oxygen does pull electrons towards itself in most resonating structures but can also donate an electron pair (acquire positive charge) if there is a positive charge on an adjacent carbon. | |
| Oct 26, 2013 at 13:55 | comment | added | stochastic13 | @mikhailcazi That is because, relatively, as compared to other carbons, the one with a positive charge in one of the resonance structure is slightly positive and hence more prone to attack of nucleophile $\ce{Br-}$. It doesn't add on the oxygen because the lone pairs of oxygen in both the resonance structures repel the incoming nucleophile, which cannot form a bond with oxygen. | |
| Oct 26, 2013 at 13:32 | comment | added | F'x | Between A and B, look at how the octet rule is satisfied for the carbon atom (and not the oxygen)… | |
| Oct 25, 2013 at 15:39 | history | tweeted | twitter.com/#!/StackChemistry/status/393763679650734080 | ||
| Oct 25, 2013 at 14:37 | comment | added | mikhailcazi | While adding Br$^-$ to the compound, why do we take the reaction further by adding it to compound (A), then? :/ | |
| Oct 25, 2013 at 14:36 | comment | added | mikhailcazi | So you say that option (B) is more stable? | |
| Oct 25, 2013 at 14:28 | comment | added | stochastic13 | I guess the octet is complete in both the cases. But for the stability of these resonance structures, points to considered in decreasing order of importance are higher number of bonds; complete octet; charge separation; +charge on electropositive and -charge on electronegative elements. | |
| Oct 25, 2013 at 12:21 | history | edited | mikhailcazi | CC BY-SA 3.0 |
edited title
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| Oct 25, 2013 at 11:45 | history | asked | mikhailcazi | CC BY-SA 3.0 |