For each of the following pairs, indicate which member is the more stable:

Name: Problem 45, Chapter 4: Organic Chemistry
Uploaded: 2021-04-23T17:16:49-08:00
Duration: 6 min 53 s
Channel: Temi Ajayi
Description: For each of the following pairs, indicate which member is the more stable:

For each of the following pairs, indicate which member is...

Key Concepts

Inductive Effects

Inductive effects involve the shifting of electron density through sigma bonds due to the electronegativity differences of substituents. Electron-donating or electron-withdrawing groups can stabilize or destabilize a molecule by altering electron distribution, thereby affecting the overall stability.

Steric Effects

Steric effects arise from the physical interference of atoms or groups within a molecule, leading to repulsive interactions when groups are too close to one another. Molecules with less steric hindrance usually experience reduced strain and are thus more stable.

Resonance Stabilization

Resonance is a key factor in molecular stability. Structures that can delocalize electrons over multiple atoms through resonance tend to have lower energy and higher stability, because the electron density is spread out over a larger framework rather than localized in a high-energy configuration.

Hyperconjugation

Hyperconjugation refers to the stabilizing interaction that occurs when electrons in a sigma bond (usually C–H or C–C) interact with an adjacent empty or partially filled p-orbital or pi system. This delocalization of electron density can significantly lower the overall energy of a molecule, enhancing its stability.

Comparative Molecular Stability

This concept involves evaluating the relative stability of molecules by comparing their overall energy states. A more stable molecule generally has lower energy, which translates into greater thermodynamic favorability and resistance to chemical change or decomposition.

Transcript

00:01 So here we are looking at stability of some intermediates and substrates.

00:08 Okay, so if we start off with this tertbutal carbacallion versus the linear beetle form, okay? so basically do have the exact same like molecular formula, there are isomers with one another, but as you can tell, we all know that sherry carburetokanions are more stable than secondary or more stable than primary carburetokanisans okay so with that we know that the tuributal cation is more stable and the exact same thing would happen if these were radicals as well okay okay carbiccan stability or radical stability follows similar rules carbocyan stability so it would basically follow the exact same thing over there for that example okay now let's say we had a purple carbocontion with another purple halide carburetion so then which one would be most stable so that being said these ones are quite similar so not wondering what this chlorine does.

01:46 So if you know chlorine, chlorine is very electronegative atom and it's also an electron withdrawing.

01:54 So this is an electron withdrawer.

01:59 Okay, so that's not really what a carbotlion would want to stabilize itself.

02:04 Electron donating groups would be more useful to increase stability.

02:12 So with that, we know that this without the electrical giant group is the more stable species.

02:21 Okay, just simply due to its intense electronegative nature.

02:31 Alright, so now, if you just move on to this one, this is rule that is shown here.

02:39 Secondary radicals and kerbicolions are also more stable than primary radicals.

02:43 So that just deals with the next example.

02:46 Okay, so now let's look at methyl 2 methyl, kind of an isoprene unit here.

03:00 So let's look at this structure versus this one.

03:08 So we have five.

03:11 Okay, so if you look at those two alkenes, what we basically see here is we need to look at the alkenes substitution.

03:29 Okay, and we know that the higher the substitution, the more stable the alkyne is...

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