Can we form Are pi bond like overlaplike interactions possible when substituents in a compound are not directly connected?

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edit approved Oct 15, 2020 at 17:58

Brian

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Identifyidentify the more acidic compound (and the answer is the III is more acidic than II ).

My reasoning: Consider II compound, we have oxygen attached to the carbon forming a sigma and a $\pi$ bond, this oxygen has two filled p orbitals. The oxygen in the ortho position to it (in II), also has two filled p orbitals. My theory is that as we have filled p orbitals, they can form a $\pi$ bond type interactioninteractions (*). After forming the two $\pi$ bonds, the compound is stable.

Now discussing III, applying the same idea as above, Therethere is a larger distance for the pi$\pi$ overlap and hence I think $\pi$ overlap is less stable compared to the case in II.

Hence, we can say that III is more acidic (**) than II, as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance.

I reached at the correct answer but I am not sure if my reasoning for it is correct because I haven't seen directly similar explanations in textbooks, however, I felt this idea was hinted at.

*: Not a $ \pi$ bond in the strong sense of the word

**: Less stable

Identify the more acidic compound (and the answer is the III is more acidic than II ).

My reasoning: Consider II compound, we have oxygen attached to the carbon forming a sigma and a $\pi$ bond, this oxygen has two filled p orbitals. The oxygen in ortho position to it (in II), also has two filled p orbitals. My theory is that as we have filled p orbitals, they can form a $\pi$ bond type interaction (*). After forming the two $\pi$ bonds, the compound is stable.

Now discussing III, applying the same idea as above, There is a larger distance for the pi overlap and hence I think $\pi$ overlap is less stable compared to the case in II.

Hence, we can say that III is more acidic (**) than II as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance.

I reached at the correct answer but I am not sure if my reasoning for it is correct because I haven't seen directly similar explanations in textbooks, however, I felt this idea was hinted at.

*: Not a $ \pi$ bond in the strong sense of the word

**: Less stable

identify the more acidic compound (and the answer is the III is more acidic than II ).

My reasoning: Consider II compound, we have oxygen attached to the carbon forming a sigma and a $\pi$ bond, this oxygen has two filled p orbitals. The oxygen in the ortho position to it (in II), also has two filled p orbitals. My theory is that as we have filled p orbitals, they can form a $\pi$ bond type interactions (*). After forming the two $\pi$ bonds, the compound is stable.

Now discussing III, applying the same idea as above, there is a larger distance for the $\pi$ overlap and hence I think $\pi$ overlap is less stable compared to the case in II.

Hence, we can say that III is more acidic (**) than II, as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance.

I reached the correct answer but I am not sure if my reasoning for it is correct because I haven't seen directly similar explanations in textbooks, however, I felt this idea was hinted at.

*: Not a $ \pi$ bond in the strong sense of the word

**: Less stable

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edit approved Oct 15, 2020 at 17:51

Brian

436
6
31

Identify the more acidic compound (and the answer is the III is more acidic than II ).

My theory as to why it must be true is, let's considerMy reasoning: Consider II compound, we have oxygen attached to the carbon forming a sigma and a pi$\pi$ bond, and thatthis oxygen has 2two filled p orbitals. Now the The oxygen in ortho position to it (in the same II), also has 2two filled p orbitals. So myMy theory is that as we have filled p orbitals, they can form a pi$\pi$ bond type interaction ( I am not calling it pi bond because I am not exactly sure*). So afterAfter forming the 2two pi$\pi$ bonds, the compound is stable.

Now discussing III, it also hasapplying the same theoryidea as the above, but itThere is just thata larger distance for the pi overlap is at a large distance and hence I think pi$\pi$ overlap over more distance is less stable consideredcompared to a small distancethe case in II. Considering this theory to be true

Hence, we can say that III is less stable (and hence more acidic (**) than II as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance. Is my theory

I reached at the correct? Any help answer but I am not sure if my reasoning for it is appreciated. Thank youcorrect because I haven't seen directly similar explanations in textbooks, however, I felt this idea was hinted at.

*: Not a $ \pi$ bond in the strong sense of the word

**: Less stable

Identify the more acidic compound (and the answer is the III is more acidic than II ).

My theory as to why it must be true is, let's consider II compound, we have oxygen attached to the carbon forming a sigma and a pi bond, and that oxygen has 2 filled p orbitals. Now the oxygen ortho to it (in the same II), also has 2 filled p orbitals. So my theory is that as we have filled p orbitals, they can form a pi bond type interaction ( I am not calling it pi bond because I am not exactly sure). So after forming the 2 pi bonds, the compound is stable. Now discussing III, it also has the same theory as the above, but it is just that the pi overlap is at a large distance and I think pi overlap over more distance is less stable considered to a small distance. Considering this theory to be true, we can say that III is less stable (and hence more acidic) than II as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance. Is my theory correct? Any help is appreciated. Thank you.

Identify the more acidic compound (and the answer is the III is more acidic than II ).

My reasoning: Consider II compound, we have oxygen attached to the carbon forming a sigma and a $\pi$ bond, this oxygen has two filled p orbitals. The oxygen in ortho position to it (in II), also has two filled p orbitals. My theory is that as we have filled p orbitals, they can form a $\pi$ bond type interaction (*). After forming the two $\pi$ bonds, the compound is stable.

Now discussing III, applying the same idea as above, There is a larger distance for the pi overlap and hence I think $\pi$ overlap is less stable compared to the case in II.

Hence, we can say that III is more acidic (**) than II as the pi overlap of the p orbitals of the two oxygen atoms are farther and long in III, and II is more stable (less acidic) as the pi overlap is over a small distance.

I reached at the correct answer but I am not sure if my reasoning for it is correct because I haven't seen directly similar explanations in textbooks, however, I felt this idea was hinted at.

*: Not a $ \pi$ bond in the strong sense of the word

**: Less stable