physics chemistry maths science forums
become expert I help I sign up I login
refer a friend - earn nickels!!   
 advanced
 
Home
Ask & Discuss Questions
Study Material
Experts Zone
Hang Out!

Ask & Discuss Questions with Community & Experts

Moderation Team
 90 chars left    advanced
Ask iit jee aieee pet cbse icse state board community Community Discussion Question: A DIFF. ONE tautomerism 2 ; THE ONE WITH HIGHER ENOLIC CONTENT
Forum Index -> Organic Chemistry like the article? email it to a friend.  
Author Message
x4 (300)

Scorching goIITian

Olaaa!! Perrrfect answer. 52  [72 rates]

x4's Avatar

total posts: 280    
offline Offline

HEY GUYS AGAIN THE ONE WITH HIGHER ENOL CONTENT GIVE REASONS .


 


        O           O


         ||            ||


Ph---C---C---C---C                     COMPOUND 1


                 |


               Cl


 


 


        O           O


         ||            ||                             COMPOUND 2


Ph---C---C---C---Ph


 


COPYRIGHT :
The copyright for the facts written above is held by x4
no part of the facts may be reproduced , stored in ur memory , or transmitted by any means without pror written permission from x4
****VIOLATERS ARE LIABLE FOR PROSECUTION UNDER THE " X4 GOIIT ACT 2008 ".****
    
sandeepramesh (1245)

Blazing goIITian

Olaaa!! Perrrfect answer. 201  [321 rates]

sandeepramesh's Avatar

total posts: 1179    
offline Offline

Wont it be 2? Extended conjugation?

 this reply: 2 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
tarinbansal (3247)

Blazing goIITian

Olaaa!! Perrrfect answer. 565  [776 rates]

tarinbansal's Avatar

total posts: 2308    
offline Offline
I am not totally sure but I think the answer shud be Compound-1.

Probable reasons-
1- First of all the H in compound 1 is more acidic than that of compound -2.
2- On forming the enol form of both compounds and comparing the stability of C=C, we see that no. of hyperconjugative structures, i.e, no of alpha H is more in Compound-1 than in Compound-2 thus stabilising its C=C more.
3- Cl, C=C, OH form a continuous chain of conjugation.

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

It is during our darkest moments that we must focus to see the light.

Check out my blog at:
http://tarinbansal.blogspot.com/
(A must see for every student)

Back to goiit, this time with Baby Veerappan. :D
 this reply: 5 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
anandghegde (1697)

Blazing goIITian

Olaaa!! Perrrfect answer. 299  [400 rates]

anandghegde's Avatar

total posts: 1062    
offline Offline

 it has to be second one.......dibenzoyl methane.........it exists 100% in enol form.....keto form negligible.......


"I a universe of atoms.......an atom in the universe"
 this reply: 10 points  (with Olaaa!! Perrrfect answer.   in 2 votes )   [?]
 
You have to be logged on to rate
  
tarinbansal (3247)

Blazing goIITian

Olaaa!! Perrrfect answer. 565  [776 rates]

tarinbansal's Avatar

total posts: 2308    
offline Offline
Umm, PLZ tell me why second one exists more in enol form than the first one?????
I mean what is wrong in the reasons given by me???

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

It is during our darkest moments that we must focus to see the light.

Check out my blog at:
http://tarinbansal.blogspot.com/
(A must see for every student)

Back to goiit, this time with Baby Veerappan. :D
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
anandghegde (1697)

Blazing goIITian

Olaaa!! Perrrfect answer. 299  [400 rates]

anandghegde's Avatar

total posts: 1062    
offline Offline

are u from b'lore?


if yes, u go to BASE?


 


"I a universe of atoms.......an atom in the universe"
 this reply: 5 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
tarinbansal (3247)

Blazing goIITian

Olaaa!! Perrrfect answer. 565  [776 rates]

tarinbansal's Avatar

total posts: 2308    
offline Offline
Arre koi mera doubt clear karegaaa ya nahiiiii ?????? :x

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

It is during our darkest moments that we must focus to see the light.

Check out my blog at:
http://tarinbansal.blogspot.com/
(A must see for every student)

Back to goiit, this time with Baby Veerappan. :D
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
sandeepramesh (1245)

Blazing goIITian

Olaaa!! Perrrfect answer. 201  [321 rates]

sandeepramesh's Avatar

total posts: 1179    
offline Offline

see 2nd one has large extended conjugation over the first one so more resonance structures no?

 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
sandeepramesh (1245)

Blazing goIITian

Olaaa!! Perrrfect answer. 201  [321 rates]

sandeepramesh's Avatar

total posts: 1179    
offline Offline

wait ill give a diagram :)

 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
anandghegde (1697)

Blazing goIITian

Olaaa!! Perrrfect answer. 299  [400 rates]

anandghegde's Avatar

total posts: 1062    
offline Offline

i am damn sure ......i have the enol content percentages of many compounds:t :t


"I a universe of atoms.......an atom in the universe"
 this reply: 10 points  (with Olaaa!! Perrrfect answer.   in 2 votes )   [?]
 
You have to be logged on to rate
  
sandeepramesh (1245)

Blazing goIITian

Olaaa!! Perrrfect answer. 201  [321 rates]

sandeepramesh's Avatar

total posts: 1179    
offline Offline

even im sure! see this :D


 


 this reply: 5 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
anandghegde (1697)

Blazing goIITian

Olaaa!! Perrrfect answer. 299  [400 rates]

anandghegde's Avatar

total posts: 1062    
offline Offline

 if u are in BASE, u shouldnt be asking this......:huh


u know why:t :t 


"I a universe of atoms.......an atom in the universe"
 this reply: 10 points  (with Olaaa!! Perrrfect answer.   in 2 votes )   [?]
 
You have to be logged on to rate
  
ashish040191 (135)

Blazing goIITian

Olaaa!! Perrrfect answer. 17  [42 rates]

ashish040191's Avatar

total posts: 319    
offline Offline

point of diff. is the presence of 1 Cl atom in the 1st molecule. Due to it, the H becomes more acidic and easily lost to form enol. hence greater enol content(extended resonance is present in both the molecule.


moreover, if the conversion is base catalized then rate of conversion is very much faster in 1st molecule>>>>>>>>>>>>>>>>>>>>>>>>>>>>

 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
sandeepramesh (1245)

Blazing goIITian

Olaaa!! Perrrfect answer. 201  [321 rates]

sandeepramesh's Avatar

total posts: 1179    
offline Offline

excuse me, 1st molecule doesnt have another Ph! What about that!