JEE Chemistry Club

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Anonymous

02:16

The answer is (C) @Jasmine @Abcd

Anonymous

My teacher gave me hint for carbene formation, didn't understand.

Anonymous

For the second question ^

Anonymous

Oh okay, for first question, I got that I2 will be first but was confused about second position. Got it now, because of repulsion in F2 it is places second.

Jasmine

05:21

@IceInkberry will be C only as the double bond in that pent diene will act as nucleophile and Cl and Br will leave as nucleophiles and the C left with F will attack on that nucleophile and C be formed as major

2 hours later…

Abcd

07:12

@Ice ^

starunique2016

conversion of salicylic acid to acrylic acid

hey thats classic reiman teiman

ANyone there?

Abcd

@starunique2016 Whats your question?

@starunique2016 What?

Abcd

07:28

oh that conversion, no idea about that.

Abcd

07:41

DNE

Avnish Kabaj

@Abcd where do you get the paper s from?

@Abcd what's the answer to that question

@Abcd ..

@Abcd ''''

Abcd

@AvnishKabaj My sir sent it

@AvnishKabaj its PhN(NO)CH3, (we did it in class as well) ...I think you will also do it during amines

Gaurang Tandon

I got a ping from @Abcd ?

Avnish Kabaj

08:00

@Abcd arigato abcd-san

Hema

Why is 3-chloro-5-(1-methylethenyl)cyclopenta-1,3-dien-1-ol named so? when applying lowest locant rule in the numbering (1-methylethenyl) gets 2 and Cl gets 4. (2,4) is less than (3,5). Why then is lowest locant rule not applied here?

Jasmine

08:19

@Abcd only one equivalent of OH anion given so last HCl formed

Makes no difference though

@Abcd amines will be done tomorrow

Anonymous

08:47

Thanks @Abcd and @Jasmine!

Abcd

08:59

@Jasmine Huh? No where its written "1 equivalent"

@AvnishKabaj @GaurangTandon @Jasmine Which hellish reaction is this O_O ?

Abcd

09:25

@AvnishKabaj ?

Avnish Kabaj

@Abcd haven't done amines

starunique2016

Conversion for salicylic acid to acrylic acid

You can look up the structures.

2-Hydroxybenzoic acid

propenoic acid

Abcd

@AvnishKabaj its of carbonyl

starunique2016

ammonium carbonate is a salt of weak base and salt.

Avnish Kabaj

@Abcd question number

Abcd

09:40

@AvnishKabaj check 120 around

@AvnishKabaj 127

@AvnishKabaj saw?

Avnish Kabaj

Will see later

2 hours later…

Gaurang Tandon

12:11

@Abcd idk

Anonymous

12:51

@Abcd Paal-Knorr

Anonymous

Maybe

Anonymous

Not in JEE syllabus, I think.

Abcd

13:40

@IceInkberry Yeah, done that much. But the one after that is scarier. What does CCl3COONa do ?

Anonymous

Haha, Don't know :P I haven't reached that chapter yet.

Jasmine

14:31

@Abcd isnt it understandable i mean if its not written then we take 1eq

Jasmine

14:51

@Abcd i have completely no idea even i didnt know whats Paal Knorr seems like our sir forgot to teach

Anonymous

@Hema Because, draw the structure from the first name. The numbering starts from alcohol.

Anonymous

@Jasmine Do you not check from your FIITJEE modules what is taught what is not? (Or the modules aren't that good?)

Jasmine

@IceInkberry i never open package for theory but ok i will see

Anonymous

It doesn't seem to be in syllabus

Anonymous

15:04

Abcd

@Jasmine even I didnt know it, I searched it on net and got it.

@IceInkberry Its just a logical reaction, you can predict the mechanism yourself

Anonymous

@Abcd Yeah, sorta!

Jasmine

@IceInkberry is it allen package

Anonymous

I am saying that like specifically it's not mentioned anywhere by name

Abcd

@IceInkberry then you can go to the extent of saying that only those 5-6 named reactions are in JEE syllabus ...which is wrong obviously

Anonymous

15:06

@Jasmine We haven't reached that chapter yet

Jasmine

Yeah even i searched on net

Abcd

@IceInkberry almost every reaction has a name .... we arent taught all names.

Anonymous

And anyways, they have stopped giving us theory modules.

Jasmine

@IceInkberry ?!

@IceInkberry is that not allen module and dod you leave allen

Abcd

@Jasmine do you know anything about star's problem?

@Jasmine why would she leave allen -_-

Anonymous

15:07

@Jasmine For organic, from alkyl halides onwards(current chapter), we will only get modules having only questions.

Jasmine

@Abcd what

Anonymous

@Jasmine That's FIITJEE

Abcd

6 hours ago, by starunique2016

Conversion for salicylic acid to acrylic acid

@Jasmine This one

Jasmine

@IceInkberry i had a feeling lol

Abcd

@IceInkberry yeah it had fiitjee colour scheme and i was wonering why allen gave such thing

Anonymous

15:08

I heard that it is given in NCERT long ago in this very room? Idk

Abcd

@IceInkberry Ohh

Jasmine

@Abcd i thought as well

Abcd

@IceInkberry chat.stackexchange.com/search?q=Paal+&room=74807

@IceInkberry From whom did you hear it

Anonymous

I was talking about star's question

Abcd

@IceInkberry Oh that. Who said its given in NCERT

Q: Conversion of salicylic acid to acrylic acid.

This question was asked in chat by another user. I couldn't think of any reaction procedure that could do this. How do we carry out this conversion? I remember preparing acrolein from ethyl orthoformate and $\ce{NaHCO3}$ and then it's oxidation with Tollen's reagent would give acrylic acid. But...

@IceInkberry chat.stackexchange.com/search?q=acrylic&room=74807

Anonymous

15:11

@Abcd Okay, I don't know, I just said that I think I had heard this question somewhere here and blah blah NCERT was the source. Lemme investigate.

Anonymous

I give up ;-;

Anonymous

Must have heard somehwere else

Hema

@IceInkberry but the numbering can go in both directions right? Is is done in this way so that both ends of the double bond starting at OH get the numbers 1,2?

Anonymous

Oh no, it was something else @Abcd Nvm Sorry

Anonymous

@Hema The ring is 5 membered and the postion five is equivalent to first position. How can you go other way and get 4 for it?

Hema

15:17

@IceInkberry ohhh ok got it, I had actually forgotten that we have to apply lowest locant rule to corresponding groups, I thought that since 2 was less than 4 we could put it. Thank you so much!

Abcd

@starunique2016 could you please tell the source of the question?

@Ice could you ask your teacher about this?

Anonymous

@Abcd He's out of town for a week and we are all by ourselves. Haha.

Anonymous

Also, we haven't reached that chapter yet.

Anonymous

15:37

@Abcd How do I convert a compound with Aldehyde and carboxylic acid into alkene without distirbing COOH part?

Jasmine

@Abcd i am familiar to decarboxylation of salicylic acid and the question seems a bit difficult to me

Anonymous

56 secs ago, by Ice Inkberry

@Abcd How do I convert a compound with Aldehyde and carboxylic acid into alkene without distirbing COOH part?

Anonymous

@Jasmine

Jasmine

@IceInkberry can you give the exact q. Is it cyclic or open chain

Anonymous

Abcd

15:42

@IceInkberry Tautomerise in basic medium then E1Cb by heating hard

Avnish Kabaj

The heck

Aah

After aldol you'll have to do Wolff kishner as well

But that's not what ice is asking

Abcd

@AvnishKabaj Huh? why aldol for Ice's question

@AvnishKabaj i never told her to do aldol

Jasmine

Attack by KOH and tautermerisation

Abcd

@Jasmine I said the same thing

Then E1Cb

Jasmine

Back conjugation can happen by O

Avnish Kabaj

15:45

@Abcd that will make an alkyne

Jasmine

And then negative charge by C generates pi bond

Avnish Kabaj

No that will undergo beta decarboxylation

Abcd

oh sad

Jasmine

@Abcd what?

Please use names to avoid confusions

Anonymous

Idk what's going on. But to convert salicylic acid to acrylic one. I did ozonolysis (It will have many products but nvm; the one above will be also one of them). Then do what jasmine said to convert the aldehyde part to alkene.

Anonymous

15:47

An extremely ineffecient way

Abcd

@IceInkberry yeah i tried this exact same thing in morning

Anonymous

Oh really? High five! :P

Anonymous

I feel so helpless that I am thinking just on the basis of what I have learnt in hydrocarbons.

Jasmine

Why do i get notificatio of events in h bar room

@IceInkberry did you find acrylic acid wow

Anonymous

I don't know

Jasmine

15:56

Where am i wrong in doing back conjugation to convert the given compound to alkene

Anonymous

(By the way, I don't even know what back conjugation means)

Jasmine

@IceInkberry taking of pi electron and then giving it back to C

I wanted to generate negative charge on C thats why

Bye bye need to go

Abcd

16:58

8 hours ago, by Abcd

@IceInkberry Please let me know the way to bookmark messages. I want to bookmark my following messages.

orgsyn.org/Result.aspx?ga=na

First prepare 2,5 dimethyl pyrrole and then insert carbene into it to form stable six membered aromatic ring.

Avnish Kabaj

17:17

@Abcd how's pyrrole forming can you please send me the mechanism

Abcd

@AvnishKabaj Okay

Abcd

17:30

@AvnishKabaj link

I did it using this one though: chemistry.stackexchange.com/questions/8833/…

same thing in different (more comfortable, imine's nitrogen's lone pair's attack) format

Avnish Kabaj

17:50

Thanks @Abcd

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