How Many Chiral Centers are in this molecule?

Counting the number of Chiral Centers in a molecule.
How many atoms have FOUR different things attached to it?
Lone pairs count as "things".
This is Penicillin V.
Check me out: www.chemistnate...

[@rockyp8869]

To the people who are confused, the 2 nitrogens are NOT chiral centres, in both of the nitrogens the lone paors are delocalised, so they are NOT sp3, but effectively sp2 hybridised ,which is why they are not chiral centres, and the ans should DEFINITELY be 2 chiral centres

[@ProfessorMike]

I appreciate the effort to help others on CZcams with this material. The world needs more people like you.
However, I feel I have the Onus to help clarify for other viewers
That Nitrogen is sp2 hybridized, the lone pair of electron are in a unhybridized p-orbital; it would not be considered a chiral center.
There are only 2 chiral centers, and 4 total stereoisomers possible for the molecule you have drawn.
If people left this video thinking that the Nitrogen with the long pairs was a chiral center: They are going to do very poorly in O-Chem.

[@ghtutorials5695]

+ProfessorMike Correct, for anyone wanting to read more on this. See here: www.chem.ucla.edu/harding/tutorials/nitrogen_inversion.pdf

[@walleandeve1]

I know you put this awhile ago but I appreciate the comment. I was watching this video and pausing to test my ability to identify stereocentres, and I could only find the two as well. I've been going by the idea that a nitrogen can only act as a centre if it's in a ring.

[@jamesandonian7829]

I'm 4 years late but yes!!!! Very good!!!!!!!!

[@satyayadav4111]

I think having chiral centers and being chiral (optically actice) are two different things.
A compound can have chiral centre but still can be achiral (optically inactive). Here Nitrogen is a chiral center but not optically active due to nitrogen or pyramidal inversion.

[@knightawz]

so is n never a chiral centre?

[@SahilSharma-qn9jn]

I think Nitrogen Is not considered here as a chiral center, as Its lone pair is delocalised due to resonance. This question came in JEE (Main) 2020.

[@horridartistry]

Thanks bro I was searching for that question only 😅.

[@justarandomrookie4271]

yes,and also, in whatever circumstances, you can only count Nitrogen atoms as chiral in cyclic groups only and not in carbon chains.

[@yinjia7045]

i guess some of us mistaken chiral 'centers' as chiral 'carbon' ?
I'm new to biochemistry, thanks for explaining, your video is very helpful :))

[@Utpal-fj4hk]

Yeah
Same here
I also assumed chiral carbon instead of chiral center

[@jimmymoon557]

Yeah, and also i thought that electronepairs dont count as a , like he calls it different thing

[@esmfamil5086]

I appreciate that you also considered O to be a possibility. I have watched 10 videos so far and none addressed that.

[@peter7147]

there is ONLY 2 chiral centers, the N does not count as chiral center. the chiral centers are considered those 4 different groups attached ONLY to Carbon

[@TheLule93]

I thought the N would not participate in the evaluation because it is connected to a sp2 hybridized carbon atom...idk, I am currently practicing with a very similar molecule and the correct answer on it does not include the nitrogen. Im confused

[@bravotasker5883]

But The 2 Nitrogens Are In Conjugation.. So They Are Planar Right?..So They Cant Be Considered As Chiral Centre, Right?

[@auroralatea2953]

This video was awesome!!!!!! I wasn’t struggling with finding the chiral centers; I was struggling with determining what they were attached to. You broke it down beautifully and I understand now. Thank you!

[@inferninx]

My Orgo professor taught us heteroatoms can be chiral. Nitrogen can be chiral and change its hybridization. It's just confusing so most curriculums don't teach it. On my last exam I DIDNT indicate nitrogen chirality and lost points lol.

[@sharmapawan5578]

Very nice explained

[@AchkeineAhnung24]

looking for a video like this about half an hour now. thx man

[@shoumobanerjee8541]

It was very helpful thank you so much. The textbook explains this in terms of mirror images that is no not intuitive

[@Adam9848]

very nice voice. thank you from Nigeria

[@linaabdelshafy6524]

The best teacher ever

[@TheLule93]

I mean to say the Nitrogen that is connected to the Hydrogen

[@rachelo9oooyohannes254]

Thank you so much for this video, getting ready for Chem lecture in 45 min and you just saved my brain! Really appreciate it!🙌🏽

[@anteater2536]

thank you sir, your videos have helped me a lot.

[@josemariecordova5012]

I LOVE THE EXCITEMENT IN YOUR VOICE WHILE LOOKING FOR THE CHIRAL CENTERS. 12 OF 10!

[@jeeva1996]

i though it was 4 different groups around a C atom, so why are you counting the Nitrogen part

[@satyamtripathi7736]

Same question !!

[@gissellem1341]

A Chiral center does not have to be to be attached to a carbon, so he is correct.

[@gissellem1341]

@@satyamtripathi7736 a chiral center does not have to be attached to a carbon atom, he is correct.

[@prethishrahul3506]

It is 5 excluding NH. Because of Umbrella Inversion, NH loses it's chirality whereas, Cyclic N posses chirality.

[@artolapvetelainen3703]

I think this is wrong. I thought that chiral centers are atoms that are connected at least four different atoms or atom groups? Also when google this Penicillin, there are not any other example, where nitrogen is chiral...

[@easy461]

I disagree
The nitrogen in form of amide which is not basic
The lone pair electrons are delocalized away from nitrogen by reasonance
So the two N atoms are non chiral at all
There's 3 chairal centers of 3 carbon atoms only
And you misaked by forgetting to add carboxylic group on the beta lactam ring which is essential for activity

[@EuphoricLabyrinth]

I thought Chiral Centers related to Carbons only? My textbook definition: A "carbon" atom surrounded by four different groups ????

[@bhavyagumber3198]

Thanks a lot ...
Love from India💞💞

[@humbertoochoa1777]

Due to resonance the nitrogen is an sp2 trigonal planar and not a tetrahedral. Therefore, not a chiral center

[@chemusharma5682]

but here it deals with the unusualness of the functional groups

[@xlionheart92x]

the nitrogens in his compound are sp3

[@nitapatil5121]

The vidio is of 2015 but this help me on 2020

[@aspektn.5066]

Seen once. Shall be seen again. Great vid.

[@theamazingguy150]

My chemistry teacher said to not count the nitrogen, unless it's a quaternary amine with 4 other groups. I am very confused.

[@rushikeshreddy8044]

That is because nitrogen with a lone pair shows a phenomenon called pyramidal inversion or umbrella effect. Due to this , the nitrogen though sp³ with four different groups is not considered if one of them is a lone pair

[@theamazingguy150]

@@rushikeshreddy8044 thank you for the explanation

[@94cd5]

Thanks for the helpful video.

[@andrewcobb3919]

Makes so much more sense now, after listening to multiple people explain it and watching a few videos, this makes it clear.

[@user-ug3qb2xz6z]

Nitrogen is not chiral center because Nitrogon inversion occurs!

[@Strxwberrey]

Exactly my professor said the same thing

[@Muhammad44932]

So informative

[@maybilianna7791]

apparently, nitrogen is not chiral since I've got my test back and got the question wrong =(

[@hamrocksco1]

maybi lianna it's correct your teacher is just dumb

[@adarshchaturvedi3498]

Yes bcuse nitrogen lone pair is delocalised

[@xlionheart92x]

only carbon can be chiral

[@yz4687]

its just a prank bro

[@brandonwatson883]

This is late. That nitrogen is chiral, but due to pyramidal inversion, if you could isolate one enantiomer, it would racemize. Cannot typically be isolated. So most people ignore chiral nitrogens

[@epicamr96]

nitrogen can't be chiral
they are called groups not things
this is not penicillin V
the "square thing" is called beta-lactam ring

[@arjunverma963]

doesn't the nitrogen thing show some kind of inversion or is not relevant to chiral center

[@mustafaz7385]

Thank you for your hard working

[@satyamkumarmehta4111]

Thanks to you sir🙏

[@rubinetienne4477]

Nate your the man.

[@veerammatogare6099]

Really good explanation..
Thank you

[@garysuarez2107]

Still valuable knowledge

[@k.anusha2307]

Awesome! Really helped me a lot to revise chiral centre concept......!!! Thank you bro..

[@user-id7yf2gv3t]

Thank you so much 🌺❤

[@구름너머]

Thanks. Very helpful.

[@AryanKumar-wz4gi]

This came in my exam

[@mukhtarmuhammed8569]

Wow great i pray it comes in my exam too

[@kalasrinivasan8639]

video was really helpful
, PS; nitrogen group not chiral

[@xiaozhufang520]

Yes, it helped me lot. Thank you!

[@AwesomenessBigRock]

Thanks man, that helped me in Pharmacolgy

[@ahmddmg3076]

Very very good thanks for this Video

[@abdul-alimmuhammadisah6862]

Thanks alot this video has helped alot

[@danemarielledawat8905]

thank you :>

[@himneelborse2509]

excellent explaination sir

[@nesrinezallema2664]

Thank you very much for your explanation

[@boyisun]

Can you tell whether it is R or S for those chiral atoms apart from the top-right carbon in the square just by looking at this structure diagram?

[@harshita.835]

Love from India🇮🇳🇮🇳🇮🇳

[@user-tm4gi6yt3w]

Thanks a lot.... Really It's so helpful video 📹

[@ashnamaheen6573]

Thank u so much. It was really helpful :)

[@zairaholali3889]

Thank you for this video, but I don't think Nitrogen is a chiral center.

[@sk921]

Thank you so much sir. It was very helpful.

[@prodyutbanerjee766]

can u explain how many optically active product can be obtained due to the monochlorination of Methyl cyclohexane.

[@zt7686]

thank you

[@HMADY]

now it is esay . thank you

[@ayushjaiswal2420]

gold

[@Ishaalsariff14]

Smart way!

[@lujainawwad1526]

Thank you so much!!

[@amethystwings7337]

This video has helped me a lot..thank you! :)

[@ravichem8693]

appreciate your work to help others.... but your answer is wrong..... this molecule given by you has only 2 chiral centers......... 4 stereoisomers...... N atom of two amide groups are sp2 hybridized as C=N bond has partial double bond character ....... therefore N atoms are not chiral........ this molecule look like penicillin but lacks COOH group..... if you get it you will find 3 chiral centers........

[@prodyutbanerjee766]

how N can be chiral??its not a carbon

[@sachinsharma8823]

wrong, both nitrogens are not a chiral centre because there will be resonance between nitrogen and c=o which is atteched at the adjusent position.

[@fahadahamed1781]

How many chiral centre have atropine

[@zonko]

4 different things
4 different Death Stranding trailers

[@adelinarodriguezzahrt8363]

Thank you!!!

[@nanamimomozono1113]

Thank you so much for helping...

[@AyushDwivedi-ri4kw]

THAAAANKYOUUUUU 💖💖💖

[@fakingtrels]

But what about quantum tunneling in the nitrogen doesn't that prevent it from inverting therefore stop it from being chiral?

[@mediwise2474]

explain

[@priyamkeshwa6047]

thanks it helped a lot

[@dharmeepatel7385]

Thanks a lot man!

[@BCS_RavigowriJaswanth]

How can we find the no of sterio isomers in same structure

[@RemiTa1st]

this is penicillin V structure missing the COOH

[@emirafatimah]

thank you ❤️

[@RollnoUopmthirdyear-rl9de]

Thank you

[@shaboatrad4066]

What if it has A double bond with oXygen and a bond with H and A bond with C

[@f.l.8761]

Thanks a lot ;)

[@KA11LMA]

So does this mean when searching for chiral centres we can dismiss all double bonds?

[@tobinos8018]

Yes because with a double bond,the carbon would have 3 groups around it not 4

[@suzyleonhanna8866]

chirality is a character related to only carbon not any other atom

[@organistitigullio3866]

+suzy leon hanna No. Any tetrahedral atom that has bonds with four different atoms can be a chiral centre. Usually it is a carbon.

[@sachinsharma8823]

wrong,there will be any atom chiral centre provided it should be atteched with four different things

[@meetbrahmbhatt1531]

Not necessarily

[@syahira7786]

GUYS...NITROGEN CANNOT BE CHIRAL CENTER...ONLY CARBON... CHIRAL CENTRE IS DEFINED AS SP3 HYBRIDISED CARBON ATOM👈 (only carbon) WITH FOUR DIFFERENT ATOMS OR GROUPS BONDED TO IT....

[@pawanprakash4131]

In Ammonium ion Nitrogen is chiral... It can be Chiral but in this case there is quantum tunnelling of lone pair changing the hybridization or through the inversion and due to this a racemic mixture is formed and the resultant molecule becomes inactive so the nitrogen can't be considered as the stereocentre... but in some cases it can be chiral...

[@sorianasor9730]

How many diastereomers can be in this molecule ?

[@BlackFiredDragon]

You sound kinda like Tom Cruise...

[@oritsuyosai1370]

Thank you

[@geofreynderitu9137]

hapo sawa a very good lesson

[@miaeba]

the answer guide in my text says this is incorrect.

[@monicanobbay3710]

i love you Nate, you've helped me understand chirality!!!!!!! THANK YOU SO MUCH

[@princesilvestinrajneolashe9664]

Thank you sir😊

[@AndrewShehata3]

The nitrogen is not chiral!

[@AznJJLinCpopstar]

It is Chiral because there are 4 different bonds coming off of it.

[@drewskeez1156]

Neutral nitrogens with three substituents are not chiral. Positively charged nitrogens with three subsituents are chiral. Anyways, it does not have 4 bonds with anything. It has three with a lone pair.

[@pcchemistry6745]

but nitrogen have bulky group that's it's will not inverse in umbrella form, so it is chiral

[@RandomGirlDiana]

you saved my ass thank you

[@helinorhan]

thank youuu

[@aongocnganha2246]

Thank you 😘😘😘😘. Helped a lot :>>

[@anshulraturi6655]

N ni hoga chiral vo resonance mai hai

[@thedestroyer5825]

شكرا.الشرح واضح جدا

[@krokodilledertasche8412]

Thank you very much sir :)

[@SuperSimpleasthat]

A lone pair of hydrogen and a hydrogen is the same thing so Nitrogen is not chiral