An Ochem Q regarding aromatic substituents

YO on the NS FL #1, the passage that covers questions 48-52 on CP tells me that an aromatic ring with an NO2 substituent DONATES in electron density, thus stabilizing a nearby carbocation. I can't seem to wrap my head around how NO2 would/could ever donate in electron density. Here's a photo of the molecule I'm talking about:

In the passage, this molecule has the most negative RSE, which we are told is an indicator of stability. (More neg=more stable carbocation).

THANKS IN ADVANCE!

๐Ÿ‘︎ 3
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/HecticANALysis
๐Ÿ“…︎ Oct 29 2018
๐Ÿšจ︎ report
C=C conjugated to aromatic ring as substituent?

What sort of directing and activating/deactivating effects would a C=C bond have when conjugated with an aromatic ring system? (ie. at the benzylic position)

In drawing resonance structures for it, I find I can either place a negative or positive charge in the ring, and so I'm not sure which really occurs.

Without drawing resonance structures, it appears to be an alkyl substituent...so therefore mildly activating and an ortho- para- director? That's what I would guess resonance aside...

But I know resonance has to have something to do with this (it's conjugated...I have a feeling it's important somehow) but not sure how...

Can anyone help?

๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/xn3x
๐Ÿ“…︎ Mar 09 2016
๐Ÿšจ︎ report
Why are meta direting substituents on benzenes slow Electrophilic Aromatic Subsitution reaction?

I know they all in general slow it down. But, why? I mean because it decreaes amount of negative electron density spots on the molecule making it a shitty nucleophile?

๐Ÿ‘︎ 11
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/FallsZero
๐Ÿ“…︎ Sep 15 2019
๐Ÿšจ︎ report
Canโ€™t seem to figure out this mechanism, all I can gather is that I have a electron donating group on benzene which will direct para. Iโ€™ve seen AlCl3, I may have to use it in some way of an electrophilic aromatic substitution but can seem to see how that would work. I could be wrong altogether.
๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/ConferenceVast736
๐Ÿ“…︎ Nov 23 2021
๐Ÿšจ︎ report
Effect of SiMe3, SiEt3 Paraโ€Substituents for Exhibiting High Activity, Introduction of Hydroxy Group in Ethylene Copolymerization Catalyzed by Phenoxideโ€Modified Halfโ€Titanocenes

Remarkable effects of SiMe 3 , SiEt 3 ย  para โ€substituent in the phenoxideโ€modified halfโ€titanocenes, Cp*TiCl 2 (Oโ€2,6โ€ i Pr 2 โ€4โ€Rโ€C 6 H 2 ) [R = SiMe 3 ( 6 ), SiEt 3 ( 7 )], toward the catalytic activities in ethylene copolymerizations with 2โ€methylโ€1โ€pentene, 1โ€decene, 1โ€dodecene and with 9โ€decenโ€1โ€ol (DCโ€OH) have been demonstrated. The activities by 6 , 7 at 50 ยบC showed higher than those conducted at 25 ยบC in all cases in the presence of MAO cocatalyst. Efficient synthesis of high molecular weight (HMW) ethylene copolymers incorporating DCโ€OH (or 5โ€hexenโ€1โ€ol, HXโ€OH) has been attained in the copolymerization by 7 , which showed better DCโ€OH (HXโ€OH) incorporation at 50 ยบC to afford the HMW copolymers, poly(ethyleneโ€ co โ€DCโ€OH)s, with high activities (activity 1.21โ€“3.81ร—10 5 kgโ€polymer/molโ€Tiยทh, M n = 6.55โ€10.0ร—10 4 , DCโ€OH 2.3โ€3.6 mol %).

https://ift.tt/2R3pVrn

๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/TomisMeMyselfandI
๐Ÿ“…︎ Sep 05 2020
๐Ÿšจ︎ report
Need some help with the H-NMR Spectrum: My Task is to figure out the molecule. The peak at around 2 is DMSO d6. The next peak at 3 might be a methoxy group. The other peaks in the aromatic range give me a ortho/meta substitution and a para substitution i think. The peak at 11 might be an OH Group.
๐Ÿ‘︎ 3
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MethylMercury00
๐Ÿ“…︎ Jun 03 2021
๐Ÿšจ︎ report
Theoretical Studies on Effect of Substituent on Aromaticity of Highly Substituted Benzene Rings

In this research, effect of electronegative F, Cl, NO2 and CF3 substituents on aromaticity of highly substituted benzene molecules is studied. NICS, ASE, HOMA and HOMO-LUMO energy gaps were the indices which are applied to show effect of substituents. In addition, sigma and pi-electron donor acceptors are calculated for all the substituted molecules. Additionally, total electron donor acceptor tEDA was proposed as a new descriptor which was the sum of two previously mentioned descriptors and show total electrons.The trend of results is different for all methods. For instance the behavior of NICS is contrariwise to ASE and HOMO-LUMO energy gaps results and HOMA index calculation provided no valuable information. As other results, it was shown that the calculated NICS in center of rings was changed not only by ring current but also altered with the presence of other atoms fields. The isomerization effect of the aromaticity also was studied and it was shown that the energy, ASE, and HOMA indices adapted to tEDA descriptors. Deficiency of NICS and HOMA methods in predicting the substituent effects illuminated in this research which the NICS deficiency is explained by the fact that the chemical shift of nucleus was resulted from two sources: ring current and other atoms presence.

๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/Tradescienceinc
๐Ÿ“…︎ Feb 19 2019
๐Ÿšจ︎ report
substituents in cyclohexane which affects rate of elimination
๐Ÿ‘︎ 3
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/7ujklo98
๐Ÿ“…︎ Dec 28 2021
๐Ÿšจ︎ report
Is this ring flip correct? I canโ€™t tell where the substituents are place/ordered in the ring flip
๐Ÿ‘︎ 21
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/celluxjen
๐Ÿ“…︎ Dec 19 2021
๐Ÿšจ︎ report
Why do we not add โ€œbenzeneโ€ to the answer in the image attached since there is also a benzene ring and benzene( or phenyl in cases where it is considered to be the substituent) is a functional group? Any help is greatly appreciated. This is an image I downloaded from Google not HW.
๐Ÿ‘︎ 55
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Nov 03 2021
๐Ÿšจ︎ report
When naming alcohols, we give priority to OH but what if OH was at carbon 3 from one side and there was a B atom at carbon 2 from the other side. Like do we ignore the fact that starting with Br gives lowest numbers to substituents? TIA!
๐Ÿ‘︎ 3
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Nov 08 2021
๐Ÿšจ︎ report
Are you bisexual,gay,lesbian,trans,asexual,NB, or aromatic
๐Ÿ‘︎ 4k
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/Cod-ed
๐Ÿ“…︎ Jan 02 2022
๐Ÿšจ︎ report
About Cyano Substituents

Just something that's been irking me because I see it on this sub all the time. I've tried to comment about it before but it was removed for a reason I can't remember.

Noids with CN (cyanide) in the name are not inherently any more dangerous than other noids. A cyanide is any organic compound containing a cyano group, Cโ‰กN. It's literally just a carbon triple bonded to a nitrogen. When we talk about cyanide colloquially, we're referring to cyanide salts like sodium or potassium cyanide, which will kill you. However, cyano-containing cannabinoids are complex organic molecules that do not freely dissociate to form CN- ions. You'll be fine.

๐Ÿ‘︎ 19
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/Enamorrmusic
๐Ÿ“…︎ Nov 01 2021
๐Ÿšจ︎ report
For IUPAC nomenclature do you treat a second functional group exactly the same as a substituent or is it given higher priority than other substituents?

https://preview.redd.it/7jslgy88wm581.png?width=880&format=png&auto=webp&s=66d0d403eb60d808f65704b283afd701aab9c98d

๐Ÿ‘︎ 4
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/ihaveaplantfetish
๐Ÿ“…︎ Dec 15 2021
๐Ÿšจ︎ report
Alphabetizing complex substituents

I have an organic chem prof who says that when naming alkanes, complex substituents are alphabetized by the last "word" in the substituent (e.g. (1,1-dimethylpropyl) would be alphabetized by "p").

Furthermore, he says that if you have multiple complex substituents, you don't alphabetize them at all- you order them in the name by increasing number on the parent chain.

I've been doing a ton of research on organic chemistry tutor, ucalgary, and a few other organic tutoring sites. They all say this is NOT the way alkanes are named. Has anyone seen this method that my prof uses? Or is he just completely cracked? Am I cracked?

http://imgur.com/a/gctpkxy

๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/ungalikriver
๐Ÿ“…︎ Sep 30 2021
๐Ÿšจ︎ report
What is the best way to memorize functional groups for my orgo exam Friday?I also have to memorize the alkyl substituent names!
๐Ÿ‘︎ 29
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/mariahchanel
๐Ÿ“…︎ Sep 30 2021
๐Ÿšจ︎ report
What do you call the head of the catholic church covered in flowers and aromatic herbs?

Pope-purri

๐Ÿ‘︎ 9
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/Ixshanade
๐Ÿ“…︎ Jan 03 2022
๐Ÿšจ︎ report
Could anyone help with this. I donโ€™t understand why this cyclobutane has a plane of symmetry even though the plane doesnโ€™t give us two identical halves? I mean the ring will be split into two identical halves but the substituents will be different for each side so overall they arenโ€™t identical? TIA!
๐Ÿ‘︎ 18
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Oct 18 2021
๐Ÿšจ︎ report
What happens if you move the nitrate substituents on 2,4,6 trinitrotoluene?

I'm studying organic chemistry with a student and we got to asking why the nitrates on TNT are in those specific spots. If you move the nitrate substituents to like the 2 3 6 or 2 3 5 spots does it really mess up the molecule?

๐Ÿ‘︎ 4
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/bjos144
๐Ÿ“…︎ Nov 17 2021
๐Ÿšจ︎ report
For substituted amphetamines, what is responsible for the positive correlation between the the lipophilic character of a para-substituent, and the ability of molecule to inhibit monoamine oxidase?

Additionally, how significant of a role does the inhibition of MAO play in the increase of extracellular dopamine concentrations compared to the molecule's competitive inhibition of dopamine reuptake, or its properties as a dopamine releasing agent?

๐Ÿ‘︎ 10
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/inquilinekea
๐Ÿ“…︎ Sep 28 2011
๐Ÿšจ︎ report
Could anyone help with this. I donโ€™t understand why this cyclobutane has a plane of symmetry even though the plane doesnโ€™t give us two identical halves? I mean the ring will be split into two identical halves but the substituents will be different for each side so overall they arenโ€™t identical? TIA!
๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Oct 18 2021
๐Ÿšจ︎ report
which is the correct structure for this molecule? How do I know which substituent is the wedge or dash? Or does it not matter
๐Ÿ‘︎ 20
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/celluxjen
๐Ÿ“…︎ Oct 25 2021
๐Ÿšจ︎ report
Guys, the answer key says that for this structure the IUPAC name has to be 3-chloro-1-flouropropane. I got 1-chloro-3-flouroprpane because either end will give us the same numbers for substituents but C comes before F. Is the answer key wrong? TIA! reddit.com/gallery/pukiw8
๐Ÿ‘︎ 4
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Sep 24 2021
๐Ÿšจ︎ report
Crystals of a trifluoromethylthio substitued aromatic hydrocarbon labphoto.tumblr.com/post/โ€ฆ
๐Ÿ‘︎ 2
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/ciiiiib
๐Ÿ“…︎ May 18 2014
๐Ÿšจ︎ report
How do you know when benzene is a substituent and when it is not? For example, ethylbenzene could easily be phenylethane? I am really confused. Any help will be greatly appreciated. If thereโ€™s no โ€œclearโ€ rule, then it doesnโ€™t make sense to me how IUPAC is okay with this unnecessary ambiguity. TIA!
๐Ÿ‘︎ 6
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/MedS03
๐Ÿ“…︎ Oct 09 2021
๐Ÿšจ︎ report
Why wouldnโ€™t the isopropyl be numbered as C1 since itโ€™s the larger substituent? (Topic is disubstituted Cyclohexane for reference)
๐Ÿ‘︎ 7
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/crystal8915
๐Ÿ“…︎ Sep 26 2021
๐Ÿšจ︎ report
Limonene - the aromatic terpene found in citrus peels
๐Ÿ‘︎ 1k
๐Ÿ’ฌ︎
๐Ÿ‘ค︎ u/bbundles13
๐Ÿ“…︎ Dec 24 2021
๐Ÿšจ︎ report

Please note that this site uses cookies to personalise content and adverts, to provide social media features, and to analyse web traffic. Click here for more information.