Aromaticity of Charged and Heterocyclic Compounds

Leah4sci.com/ar... presents: Aromaticity of Charged and Heterocyclic Compounds
Need help with Orgo? Download my free guide ’10 Secrets to Acing Organic Chemistry’ HERE: leah4sci.com/or...
The most difficult aromaticity topic involves charged compounds (cations and anions) as well as heterocyclic compounds, molecules that have more than just carbon and oxygen in their ring.
This video walks you through a simple process for identifying aromatic, non-aromatic and antiaromatic anions, cations, and heterocycles.
In this video:
[0:30] Characteristics of aromatic molecule
[1:53] Overview of resonating system
[2:49] Cyclopentadiene sample problem
[3:43] Analyzing Aromatic Anions
[6:48] Review of Heterocyclic Compounds
Links & Resources mentioned in this video:
Resonance video series: leah4sci.com/re...
Catch the entire Aromaticity Video Series Along with the Aromaticity Practice Quiz and Cheat Sheet on my website at leah4sci.com/ar...
Follow along with your semester by using my Orgo Syllabus Companion: leah4sci.com/sy...
For more in-depth review including practice problems and explanations, come join my online membership site the organic chemistry study hall: leah4sci.com/join
For private online tutoring visit my website: leah4sci.com/or...
For questions and comments, find me on social media here:
Facebook: / leah4sci
Twitter: / leah4sci
Instagram: / leah4sci
Pinterest: / leah4sci

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I'm sorry your professor didn't help you as much as hoped, but I'm glad my video cleared things up for you!

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It's my pleasure!

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perfect timing on this video. I just worked my way through your Aromaticity-series. Preparing myself for my upcoming Orgo 1 semester (starting next week) and you are a life saver! I love the way you explain and make the topics so much clearer and it´s easy to follow along! Thanks a bunch for your hard work. :D

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You're very welcome and thanks for the kind words. Wow your semester starts late, where do you go to school?

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So glad to hear that and that they are helping you to understand!

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Sounds like this came at a perfect time Vanessa! When is your next quiz/exam on aromaticity?

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Leah4sci this upcoming Wednesday 😅

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Just around the corner but definitely enough time to review and practice! wishing you the best on it

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I'm glad I could help! Have you seen my MCAT youtube channel yet? leah4sci.com/mcatyoutube

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You have no idea how much this helped me. I was struggling for so long with the cyclopentadienyl anion, and why it was aromatic if the C with lone pairs was sp3. I watched your video and now I completely understand the rule and feel so much better about it. I don't know if I just missed that part in class, but seriously thank you!

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Oh wow, sounds like you have a lot of catching up to do if you've been avoiding it, but better to find these videos now than after your exam. Hope they help

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So glad they've helped you, and thanks for your kind words!

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I think it has a lot to do with the fact that most lecturers/professors are not required to have teaching skills, therefore they don’t know how to relay ideas to students

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Some professors just don't know how to break things down, especially if they never had to struggle with the topic.

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You're very welcome! Glad it helped!

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I'm so glad you like it!

[@red-baitingswine8816]

4:47: For cyclopentadiene with a negative charge, that carbon has 2 C-C and one C-H bond, and one electron pair - doesn't that make 4 sp3 - tetragonal (so not planar)? (Thanks for your great work - very helpful!) . Revision - Ok I think you explained this completely later in this video when you covered Pyrrole. Thanks again!

[@Leah4sci]

I'm glad your question was answered! For help with topics like this and more, I recommend joining the organic chemistry study hall. Details: leah4sci.com/join or contact me through my website leah4sci.com/contact/

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Thank you so much!

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[@Leah4sci]

Thank you, I will

[@PanPan-km5ip]

Miss.., if I may ask, how we determine the phi electrons if the N atom no shows the lone pair? In advance thank you very much for the video..

[@Leah4sci]

The question you must ask yourself in this situation is: Does the heterocyclic atom participate in resonance? If not with a lone pair, then does it have a pi bond? If it neither forms a pi bond nor has a resonating lone pair, then the molecule does not have a conjugated system of pi electrons and is, therefore, not aromatic.

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[@graphophilic9903]

How to prove pyrene is a aromatic hydrocarbon through huckle rule?

[@Leah4sci]

This video doesn't cover the polycyclic molecule of pyrene. Unfortunately, I don't offer tutoring over social media . For help with questions like this and more, I recommend joining the organic chemistry study hall. Details: leah4sci.com/join or contact me through my website leah4sci.com/contact/

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Thank you, I will; however, I'm not a sir. :)

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[@GuineaPigLuna]

What is an atom has a negative charge, but no lone pairs? Is it still sp2 hybridized?

[@Leah4sci]

I can’t think of a situation in which you would have a negatively charged atom in a cyclic structure that does NOT have lone pairs. If you think about it, an atom with a negative formal charge has an abundance of electrons. Carbon, oxygen, and nitrogen atoms holding negative charges in a cyclic structure would all have lone pairs. Hope this helps!

[@iqramulla7429]

Can you explain the topic like annulenes and azzulene I m preparing for my 1st semester msc exam and I don't get proper notes for that topics can you explain it?

[@Leah4sci]

Unfortunately, I don't offer tutoring over social media. For help with questions like this and more, I recommend joining the organic chemistry study hall. Details: leah4sci.com/join or contact me through my website leah4sci.com/contact/

[@user-it9ey4sc9x]

If the compound is anti-aromatic .does that mean it's still has resonance? Or anti-aromatic means it's will not resonant?

[@Leah4sci]

Anti-aromatic compounds can still resonate and be conjugated, but do not follow Huckel's rule.

[@sendylamour2314]

Hi Leah, Thank you so much for this video! more than 3 years since I took orgo, apologies if my question asks for basic stuff. So, at 4:57 in the video, did you say a lone pair equals a negative charge in this case? the carbonation then, the + means a one electron? I hope my question makes sense. Thanks a lot.

[@amandeepbaghiana4510]

Very late reply, my apologies, but the lone pair is a negative formal charge (-2) because it has two free electrons. If you had a carbocation with a + on the carbon, it would have one less electron than its normal valence electrons; in the case of carbon, it would have only 3 electrons instead of 4.

[@Leah4sci]

In this case, the sp2 carbon with a lone pair held a formal charge of -1. If still looking for help with determining formal charge, see my tutorial at leah4sci.com/formal-charge-formula-and-shortcut/

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Thank you mam😊

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You're welcome!

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Thank you mam

[@Leah4sci]

Most welcome 😊

[@kristynmorales372]

I am confused as to why the carbons with cations are sp2. The carbon is bonded to two separate carbons, a hydrogen and has a lone pair. Wouldn't that make the carbon with the cation sp3 ? Help please 😭

[@Leah4sci]

Careful Kristy. Carbocations do not have a lone pair but you're right. IF a carbon has 2 carbons, 1 hydrogen and a lone pair (carbanion) it will be sp3 hybridized If carbon has 2 carbons, 1 hydrogen and an empty orbital with no electrons in it (carbocation) then it's sp2. I actually just posted a short explaining this in detail kzbin.infoshorts

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[@Leah4sci]

Wow, so happy to help!

[@spinningpersonintheworld4767]

You are awesome! Do you answer just one question? If so is cycloheptane anion aromatic? It seems if the electron joins the ring it will cause an sp carbon and make it non aromatic.

[@Leah4sci]

Thanks so much, I really appreciate your kind words! The cycloheptatrienyl anion is antiaromatic, as it has 8 electrons in its conjugated pi system. (Planar, cyclic pi systems with 4n electrons are highly unstable and antiaromatic.) No sp carbon is formed as adjacent pi electrons resonate around the ring.

[@spinningpersonintheworld4767]

@@Leah4sci that makes sense! Thank you 🙏 !

[@kavyam6665]

Mam how the carbon having anion in cyclopentadiene anion is sp2 hybridised .please help me please

[@Leah4sci]

It is due to the resonance. The lone of pair of electrons does not sit on any one carbon exclusively, so each carbon has greater sp2 character than sp3 character. (More often that not, a carbon is without the lone pair than with.)

[@solehah.a7507]

why is the carbocation sp2 hybridized tho?

[@Leah4sci]

The aromatic cation has three electron domains, consisting of two bonds to adjacent carbons and one bond to hydrogen. No lone pairs are present. We know that these three electron domains hybridize to sp2 orbitals with a single unhybridized p orbital that is open to the resonating pi system. For more on hybridization, visit leah4sci.com/OrgoBasics

[@MukeshKumar-zj2vh]

At 5.03, you said the all of the carbons are sp2 hybridized, but what about carbanion?? We have studied that carbanion show sp3 hybridization, explain plz

[@conniehsu1273]

Go to 9:25-- she explains that if the atom has the ability to resonate then it will hybridize so that it CAN resonate-- the carbon looks sp3 but it is actually hybridized to sp2 so that it CAN resonate!

[@Leah4sci]

Because this particular carbanion is resonance stabilized, it exhibits mostly sp2 character. That lone pair of electrons can exist just as equally on any of the other carbons of the ring, as it resonates throughout the structure.

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Hi mam can you suggest me only best book of organic chemistry for all topics

[@Leah4sci]

While I don't have one specific book, here are some resources I recommend for orgo: leah4sci.com/5-must-have-organic-chemistry-resources/

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@@Leah4sci Thank you so much dear

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Now I see... Now I get it... Now all the pieces are falling into place. Guess the cat is out of the box

[@Leah4sci]

Haha that's awesome! Glad it's finally clicking for you! Now that you get it, make sure to try the aromaticity practice quiz on my website: leah4sci.com/aromaticity-practice-aromatic-antiaromatic-nonaromatic/

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Thanks!

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Thanks!