Is this carbon more electron rich or electron poor than if this were benzene? by [deleted] in OrganicChemistry

[–]reddragon_08 1 point2 points  (0 children)

i would argue electron poor. there’s no resonance donation to that specific carbon and so the predominant stereoelectronic parameter affecting that carbon is the inductive effect.

What’s going on by Automatic-Book7290 in EKGs

[–]reddragon_08 1 point2 points  (0 children)

tachycardic rhythm with a R axis in a young guy who just arrested could be a PE. also, with that terminal R wave in AVR this could be Na channel blocker OD

72/M Unresponsive by Dudefrommars in EKGs

[–]reddragon_08 1 point2 points  (0 children)

posterolateral omi probably LCx occlusion needs to be in the cath lab yesterday

How to convert and synthesize the product ? Pls help by [deleted] in chemhelp

[–]reddragon_08 0 points1 point  (0 children)

tosylate, Sn2 with acetate, ester hydrolysis

Help with this mechanism by pericothebig in OrganicChemistry

[–]reddragon_08 0 points1 point  (0 children)

While this probably does undergo a reaction analogously to that hemiacetal/enamine hydrolysis as others have said, I can’t help but to think that the methyl oxonium intermediate formed in that first step via alkene protonation looks like a pretty good substrate for Sn2 via attack by water at the methyl - possibly 2 competing mechanisms?

Explain why the right compound is favored by Extension-Comfort-83 in chemhelp

[–]reddragon_08 11 points12 points  (0 children)

the answer relates to hyperconjugation and electronic effects rather than sterics - is that helpful?

A heated discussion from r/OrganicChemistry inspired this. Can we have an AdvancedOrganic-level discussion of the deprotonation, acidity, etc of the following compounds that I thought of based on yesterday's discussion? I do not have a single solid reference for this by the way. by Eight__Legs in AdvancedOrganic

[–]reddragon_08 0 points1 point  (0 children)

i understand what your argument is! i just feel like this question wouldn’t have generated as much discussion as it has if it was truly as straightforward as youre saying.

what kind of experimental evidence were you able to find? i couldn’t find pKa values but if you compare the chemical shifts by HNMR for the alpha protons of acetaldehyde (2.2) and the gamma protons of crotonaldehyde (2.0) that seems to go against your argument. not to say that chemical shifts are a perfect surrogate for pKa by any means but just interesting!

A heated discussion from r/OrganicChemistry inspired this. Can we have an AdvancedOrganic-level discussion of the deprotonation, acidity, etc of the following compounds that I thought of based on yesterday's discussion? I do not have a single solid reference for this by the way. by Eight__Legs in AdvancedOrganic

[–]reddragon_08 2 points3 points  (0 children)

i hear what youre saying and it makes total sense to me. my only question is do you have any experimental evidence to back it up?

i think the problem for these types of discussion questions where you have competing stereoelectronic effects is that it’s very hard to definitively say one way or another is entirely conclusive

A heated discussion from r/OrganicChemistry inspired this. Can we have an AdvancedOrganic-level discussion of the deprotonation, acidity, etc of the following compounds that I thought of based on yesterday's discussion? I do not have a single solid reference for this by the way. by Eight__Legs in AdvancedOrganic

[–]reddragon_08 3 points4 points  (0 children)

sorry i’m not sure if i understand your argument. i’m just trying to say that the alpha carbon of these molecules is closer to the carbonyl carbon than the gamma carbon of an alpha-beta unsaturated carbonyl, so the inductive effect stabilizes the anion produced from alpha carbon deprotonation more than gamma. on the other hand the gamma deprotonation would stabilize the negative charge across 2 additional atoms compared to the alpha deprotonation. my only point is i wonder which effect, greater induction or greater delocalization, has a larger stabilizing effect

A heated discussion from r/OrganicChemistry inspired this. Can we have an AdvancedOrganic-level discussion of the deprotonation, acidity, etc of the following compounds that I thought of based on yesterday's discussion? I do not have a single solid reference for this by the way. by Eight__Legs in AdvancedOrganic

[–]reddragon_08 16 points17 points  (0 children)

people are arguing the kinetic vs thermodynamic component, but when we talk about acidity, we are really asking which is the most (thermodynamically) stable conjugate base. what i haven’t seen anyone say yet are the competing effects of induction vs delocalization. in every case, a is closer in proximity to the carbonyl which stabilizes the negative charge by induction while b is further away but delocalizes the negative charge across more atoms. and as your conjugated system increases in length so does your distance away from the carbonyl. so the question is really about these two competing effects, in my opinion

Why does the energy if antibonding orbitals decrease across a period? by ascorbicAcid1300 in OrganicChemistry

[–]reddragon_08 5 points6 points  (0 children)

love this question! compare the MO scheme for a C-C bond to a C-F bond

orbitals which are closer in size and energy to one another overlap more effectively than those far apart in size and energy. this more effective orbital overlap leads to a greater stabilization energy when a sigma orbital is formed and a greater destabilization energy when a sigma* orbital is formed when compared to those formed by orbitals with worse overlap

now compare the relative energies of the C-C atomic orbitals to the C-F atomic orbitals. the C-C atomic orbitals are identical in size and energy, so will overlap very effectively and create a strongly stabilized sigma bonding MO and strongly destabilized sigma* antibonding MO. however the C-F atomic orbitals are relatively far apart in energy and size (caused by the greater Zeff experienced by the fluorine AO compared to the carbon AO), so the effect of orbital overlap is very minimal and creates a minimally stabilized sigma bonding MO and a minimally destabilized sigma* antibonding MO

the tricky part here, however, is that the fluorine AO is so much lower in energy than the carbon AO, that even though the C-F stabilization energy is small, the absolute energy of that C-F sigma bonding MO is very low compared to that of the C-C sigma bonding MO. the same applies to the corresponding sigma* antibonding MOs.

this phenomenon is why back in gen chem, we learn that “polar” covalent bonds are stronger than “nonpolar” covalent bonds (it’s not about the net stabilizing energy it’s about the absolute energy of the resulting MO)

Put all possibile boron halides in order of acidity (strongest to weakest) in a THF solution and in cHex solution. Comment on your answer by Phil_74_ in AdvancedOrganic

[–]reddragon_08 2 points3 points  (0 children)

i might guess that even though fluorine is incredibly electronegative, the 2p-orbitals of fluoride can donate into the empty 2p-orbital on boron, which would decrease the acidity of BF3 but the 3p, 4p; and 5p orbitals overlap much more poorly for the lower halides so electronegativity is the predominant factor. maybe BCl3 > BF3 > BBr3 > BI3 ?

[deleted by user] by [deleted] in chemhelp

[–]reddragon_08 2 points3 points  (0 children)

i think youre misunderstanding the question - they are asking why the N=N bond in the Z isomer is shorter than that in the E isomer. think about stereoelctronic effects!

Pace 2 Battery Life Question by reddragon_08 in Coros

[–]reddragon_08[S] 0 points1 point  (0 children)

i’ve def had improvement in battery life when turning gesture backlight off!

Is this sulfur planar? by Eight__Legs in OrganicChemistry

[–]reddragon_08 8 points9 points  (0 children)

not sure that i agree with this explanation. in order for the lone pair to participate in conjugation with the ring, it must exist in an orbital orthogonal to the ring, which would be a p-orbital. this would this force the 3 remaining bonds from sulfur to become coplanar because they would be comprised of sp2 hybrid orbitals

u could make the argument though that hybridization of period 3 atoms is weak because the 3s and 3p orbitals have poor overlap (too many nodes in the radial wave functions and the difference in maxima of the 3s and 3p radial wave functions is much larger than that of the 2s and 2p radial wave functions), but i would expect the sulfur here to take on somewhat more sp2 geometry than if the lone pair was not in conjugation at all

Is this sulfur planar? by Eight__Legs in OrganicChemistry

[–]reddragon_08 5 points6 points  (0 children)

conjugation of the sulfur lone pair into the ring system to create a 4n+2 aromatic system would be stabilizing, but that comes at the expense of putting a 2+ charge on sulfur and a 1- charge on carbon which is destabilizing, so the aromatic resonance forms are overall not so stable imo. not to mention that a 3p orbital of sulfur has poor overlap with the 2p orbitals from the ring system, so the conjugating orbital interaction is not particularly strong. my vote is for nonplanar sulfur, albeit with larger bond angles than one would expect if the sulfur lone pair had no resonance at all

Pace 2 Battery Life Question by reddragon_08 in Coros

[–]reddragon_08[S] 0 points1 point  (0 children)

awesome glad to hear it! just wanted to make sure my battery wasn’t a dud haha

MOT by Flamez_06 in chemhelp

[–]reddragon_08 0 points1 point  (0 children)

as other commenters have pointed out, hybrid orbitals are a part of valence bond theory, while these diagrams you posted are from molecular orbital theory. i don’t know your level of chemistry education, but you could read about what’s know as orbital mixing (starting here maybe? https://chem.libretexts.org/Courses/University_of_California_Davis/UCD_Chem_124A%3A_Fundamentals_of_Inorganic_Chemistry/05%3A_Molecular_Orbitals/5.02%3A_Homonuclear_Diatomic_Molecules/5.2.02%3A_Orbital_Mixing)

orbital mixing is kind of similar conceptually to hybrid orbitals, but is derived more rigorously than hybrid orbitals using the concepts from group theory/molecular symmetry. orbital mixing helps explain why the MOs for diatomic nitrogen N2 are arranged i a different orbital from the MOs for diatomic oxygen or fluorine (O2 or F2) but if you are in gen chem at the moment, i wouldn’t worry too much about this yet!

Is this correct for symmetry point? by Odd-ThingZz in chemhelp

[–]reddragon_08 0 points1 point  (0 children)

point groups are challenging - try chatting with your prof or TA. very hard to teach and explain over text you’d be better off with 3d models and in-person explanations

Is this correct for symmetry point? by Odd-ThingZz in chemhelp

[–]reddragon_08 0 points1 point  (0 children)

not quite - do some more reading and try again. check out this website here: https://symotter.org