Phenol Resonance and Acidity
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- čas přidán 1. 02. 2019
- leah4sci.com/alcohol Presents: Phenol Resonance and Acidity for Alcohol Reactions in Organic Chemistry
Need help with Orgo? Download my free guide ’10 Secrets to Acing Organic Chemistry’ HERE: leah4sci.com/orgo-ebook/
Phenol does not follow typical alcohol chemistry and characteristics due to it’s benzene ring and associated resonance. This video breaks down phenol and phenoxide resonance and helps you understand how this impacts acidity. Including examples with substituents like nitrophenol
In this video:
[0:27] Definition of Phenol
[3:28] Determining Acidity
[6:53] Ranking molecules based using CARIO
[11:53] Sample problems with EWG
Links & Resources Mentioned In This Video:
CARIO Acid/Base Series: leah4sci.com/acids-and-bases-i...
EAS Series: leah4sci.com/electrophilic-aro...
Acid/Base Practice Quiz: leah4sci.com/acid-base-practic...
Catch the entire Alcohol Reactions Video Series Along with the Alcohol Practice Quiz and Cheat Sheet on my website at leah4sci.com/alcohol
Follow along with your semester by using my Orgo Syllabus Companion: leah4sci.com/syllabus
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/organic-chemistry
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I loved how you used different colours to explain the concept of resonance!
Glad you liked it!
Yeap, 0 doubts
You carried me through Orgo 1, 5 years ago, and now that I'm studying for the MCAT, you're carrying me through again. Great to see your channel grow. I remember when your channel just a few thousand subscribers and I thought I had found a cache of gold.
Oh wow, thanks so much for being such a long-time loyal fan, I really appreciate it. Hope to continue living up to your 'cache of gold' compliment
@@Leah4sci People are injecting phenol on their FACES. A guy from brazil died last week after injecting this. That's crazy! People are INSANE.
You are a really great teacher - thanks for explaining this so well.
You're welcome, and thanks for the kind words!
Thank you thank you thank you so much!!! I don't understand the way my lecturers teach this at my uni, and coming back from a long study break just makes it a lot more difficult! However, this video alone helped me to grasp the concept of resonance much easier! Thank you!!!!
I'm so happy to help clear things up for you!
I love your videos so much Leah !🥰 There are such of a huge help ! (A big thank you from belgium)
You're so welcome!
(my aunt is from Belgium)
Hi , I am from Malaysia. It helps me a alot❤️ it's easier to understand.
So glad it helped you!
Thanks ALOT. I understand this concept so much better now.
You're very welcome!
Finally not an indie explanation, thank you 🙏
you're so welcome
I really enjoyed the way you explain, especially your tone. Other tutorial videos make me sleepy, you keep me engaged and interested. Thanks a lot! 🥰
Oh wow, thanks so much for your comment and kind words!
Excellent explanation . Thank you for the content .
You're very welcome!
Thank you! This helped me a lot !!
Glad it helped!
Great explanation, as always!
Thanks so much!
This was so so helpful thank u so much:)
You're so welcome!
Thank you so much I understood it fully
You are welcome!
Very well explanation. Good Job !!!!!!!!!!!
Glad you liked it!
Thank you for this great vidio you save my life 🌹
Glad to help!
thank you so much
you made my day
You're welcome! :)
It was really helpful.❤
Glad you think so!
you are the best ,how easily u switch between the colors and explain the concept
Awww, thanks!
I am bangali. I doing your class. This is very interesting. Your teaching skill amazing
Thanks so much!
Thanks mam.really helpful...
you're welcome! :)
Thank you, from Egypt ❤️
You're welcome!
Learnt very well using captions mam..
Thanks a lot..
From India 🇮🇳
You're welcome!
Wow this was such a good explanation and good examples. I actually thought it was fun....
YES! My mission to make orgo fun is successful!
@@Leah4sci Hi Leah hope you and your baby are doing well ♡♡♡ Yes, making it fun was successful, but also successful on more. A couple months ago i finally graduated from my bachelor's, 5 years in, instead of the supposed 3. What was keeping me? Organic chemistry. Years of trying to make it understood through my teacher's classes was not working but then i started watching and studying through your videos and everything was finally advancing. Now I've moved to Italy, will start a Masters in October, and I'm pretty sure I'll need to come back here but just know you helped me finish a chapter I had no idea I would be able to finish and now can start a new one and get closer in the pursue of my dreams. Best of wishes, keep up the amazing work and colorful explanation schemes and thank.you. from the bottom of my heart.
Well explained
Glad you liked it!
U r teaching method is very well......I watch ur lectures from beauty of Pakistan Gilgit baltistan
Glad to help!
Hi, thanks for your helpful videos! I just wanted to ask If you have posted the Alcohol cheat sheet or not yet bc I can't find it.
Not yet
Nice explanation ☺️☺️
Thank you 🙂
i understand EWG EDG & SN1 VS SN2. but where would i find resources describing condition's where the aliphatic chain is added to as opposed to the benzene ring? is this just anti markovnikov using peroxides as well as SN2 with strong nucleophiles so there is no carbocation intermediate for methyl or hydride shifts? ? EAS & NAS dont seem to cover this.
I don't understand your question. adding a chain to an aromatic ring would fall under Friedel Crafts in EAS
Thank you.🙏
You're welcome!
Thanks
Love you
you're very welcome
can you please explain how p-methoxy benzoic acid is less acidic than benzoic acid? Thanks.
That has to do with inductive effect rather than resonance. See leah4sci.com/acidbase
Thanks! And what about when the phenol has NH2 as substituent? I don't understand why it is less acid than phenol...
I'm sorry, but that is outside the scope of this video, 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/
Why is the formal charge on O for the deprotonated phenol (for the phenoxide ion) -1 and not 6-5=+1?? Where do the extra two electron come from when the -H left? thanks Leah
H doesn't take the electrons with it and so they wind up on oxygen
There seems to be no mention of electron density. How would you compare tertiary, secondary, primary alcohol if it weren't for electron density? Or is it accounted for by Induction?
At which specific point in this video do you have a question?
You're the best
Aww thanks!
Excellent 😇 💗 from INDIA
Thank you 🙌
Professor when 3 degree carbocatian is more stable than a 2 degree one then why 3 degree one reacts faster than 2?? It should be happier & 2 degree is more unstable hence it should react faster to gain stability
I'm sorry, but I don't offer tutoring through CZcams comments. For help with this and more, I recommend joining the organic chemistry study hall. Full details: leah4sci.com/join
Loved your video! but I just wanted to ask whether the additional resonance of oxygen will also be observed in methylphenol (where the CH3 group is covalently bonded to that C-atom of the ring which lies exactly opposite to that C-atom of the ring to which OH group is bonded)?
Yes, you should still see the same resonance pattern.
@@Leah4sci Thank you
when doing the resonance structure for phenol, how did the formal charge become negative for carbon?
The formal charge of carbon became negative because of the presence of the lone pair. The two electrons previously in the pi bond went from being shared equally between two separate carbon atoms to sitting on a single carbon atom. If you count total electrons, the carbon is sharing 3 electrons in bonds with hydrogen and the two adjacent carbons. In addition, it has the 2 electrons in the lone pair. That makes 5 electrons sitting directly on that carbon atom. (Formal charge: 4 - 5 = -1)
Based of your theory of organic chemistry,
is it possible to trap the ketal of Phenol using Dean-Stark trap, e.g. 1,4-Dioxaspiro[4.5]deca-6,8-diene [23783-59-7].
Then this can participate in a cheletropic reaction.
Alternatively, it might be possible to use 3,4-Difluorostyrene (or m,p-Dichloro) with N-Boc Pyrrole directly.
A ketene lamp is the third possibility.
I'm sorry, but 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/
@@Leah4sci thanks for inviting me.
Nice video
thanks
So wait at the end you compared phenol and ethanoic acid based on Induction (i.e the 2 Oxygen atoms vs 1 oxygen atom). Shouldn't then Induction be before Resonance? I could be wrong but doesn't Induction give rise to resonance in many cases for example in carboxylic acid where Oxygen pulls electrons and therefore produces resonance. If induction produces resonance, then why should Resonance be considered as a separate criterion or prioritized over Induction?
I believe the effect that was prioritized here was the A for "Atom", not induction. The type of atom holding the charge (oxygen over carbon) was what made ethanoate the more stable conjugate.
The practice quiz and alcohol reaction cheat sheet say coming soon on the website
Yes, we still have that in the works!
Are phenolic Good elelctrical and thermal conductivty or not..
That’s not necessarily what this video is about, but I don’t believe phenolic compounds are good conductors of heat or electricity.
thanks a lot maam
you're very welcome
I am lucky as I am a part of your channel
Good
Thanks
It's very helpful for me I am from India
Glad to help!
@@Leah4sci your heart 💓💓 is good
@@Leah4sci God bless you dear friend
Thankya for this ❤️from pakistan
You're welcome!
where does the negative charge come from 2:03 ?
After one of the pi bonds in the aromatic ring resonates on to the individual carbon, we have a lone pair sitting on an atom that is also forming three bonds - two to carbons and one to hydrogen. That makes five electrons surrounding an atom that has four valence electrons. Which means the carbon has a formal charge of -1. For more on formal charge and a shortcut for calculating it, visit Leah4sci.com/Formal
why oxygen is not happy when it is charged although it follows the octet rule in this case
Neutral molecules are more favorable than those carrying a charge. When you talk about being “happy”, molecules always prefer to be neutral and have formal charges of zero (or as close to zero as possible). When we deprotonate phenol, the oxygen bears a formal charge of -1. It is not possible for this molecule to be completely neutral, but by sharing the charge on oxygen with other atoms in the molecule through resonance, we can create greater stability for the phenoxide (as compared to the conjugate of cyclohexanol).
Phenol make resonance so Oxygen atom can distribute it's electron to the ring . This property makes phenol more acidic
Resonance of Cyclohexanol does not exist..
Am I correct mam ?
That's correct. The resonance in phenol is the cause of its greater acidity in comparison to cyclohexanol, which has no resonance.
@@Leah4sci Thank you mam
the example you gave for an adult for oxygen and children being the carbon makes so much sense.... lol thanks
You're welcome, glad it helped!
At 13:03, you switched from nitrophenol to nitrobenzene, but the compound was nitrophenol. Good video nonetheless.
oh wow good catch!!! Yes that was a... 'speako' (spoken typo) lol thanks for pointing this out
thumbs up
Thanks!
PKa of 7 is more acidic than PKa of 10 .... it's 10^3 more acidic
that is correct, did I mess that up in the video?
😻😻
Glad you liked it!
good teaching but you talk very fast
Glad you like it, and feel free to adjust the speed so my speech is slower :)