which is more stable??

› › which is more stable??

point out the more stable enol...

A) Ph-C(OH)=CH-COOEt

B) CH3-C(OH)=CH-C≡N

also give your reason!! :)

thanks in advance! :D

#Chemistry #Organic Chemistry
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16 Answers

1
Fermat ·

I think (b) is more stable because -CN exhibits greater -M effect than
-COOEt

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1
EmInEm ·

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23
qwerty ·

i go with a , coz of H bonding

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71
Vivek @ Born this Way ·

Certainly, I too go with a!

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1
Fermat ·

H-bonding is there in (b) also.
moreover the extra H-bond( =C-H:::::O=C-) may be weak due to already existing and much stronger H-bond b/w -OH::::H-C=
due to greater difference in electronegativity of O and H than the difference in C-H.
Please correct me if my reason is wrong.

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39
Pritish Chakraborty ·

-F > -O > -N for H-bonding strength. Oxygen definitely forms stronger H-bonds than nitrogen.
The hydrogen attached to C does not participate in H-bond formation. Where did you get that from?
Sorry if I sound crazy...been doing a lot of CAD work.

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Fermat ·

I had not read it anywhere. Now I have read about it.
But why isn't it possible.
According to me it should be and I think following reason should work in my favour :
i) C is more electronegative than H
ii) The carbon is sp2 hybridised
So there should be H-bonding.
and -C≡N has greater -m effect
So according to me (b) must be more stable.

Please tell if there is any mistake in my reasoning

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39
Pritish Chakraborty ·

H-bonding in C-H occurs only if there are strongly electronegative groups attached to the C atom, for example as in chloroform. The regular electronegativity difference between C and H is not enough to facilitate H-bond formation..

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karan5555 ·

i think it should be b

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49
Subhomoy Bakshi ·

answer given is b!

but WHY???!!!

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39
Pritish Chakraborty ·

Here's what I think if it's b) - Because a) can better off form a known type of compound called a beta-keto ester, and the compound is well known to exist that way...the actual reason isn't hitting my mind. Perhaps Fermat is right with -M effects of CN?

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karan5555 ·

i go with the reason gvn by fermat

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6
AKHIL ·

i too agree with fermat..

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1
EmInEm ·

fermat u are wrong Hydrogen attached to Carbon cannot take part in H bonding , if that would
hav been true then ethene should have been comparable to that of water but its boiling point is -100oC , moreover what does -M effect of CN have to do with enol stabilisation ? if u say so , then double bond of enol in 1 can delocalize with both Ph ring and COOEt group also , what do you have to say abt that then in 1 there is perfect intramolecular H bonding forming 6 membered ring , where as in 2 if u say that there is this H bonding : O-H :::: N≡C- , then that wont happen because of strain

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sairaghava94 s ·

...B............................BECAUSE THE ALCOL GROUP IS HAVAING BOND WITH SP3 CARBON AND IT CAN EXHIBIT TAUTOMERISM

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bhaarat ·

Okay.. can we take it this way.. let us consider the keto forms of both the compounds,
IN a) THE CARBONYL CARBON IN THE KETO FORM IS RESONANCE STABILISED FROM THE ADJASCENT BENZENE RING..

HOWEVER THIS DOES NOT OCCUR IN b). HENCE KETO FORM OF a) IS MORE STABLE THAN KETO FORM OF b)..
OR CONVERSELY.. ENOL FORM OF b) IS MORE STABLE THAN ENOL FORM OF a) .....

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Your Answer

H
49
Asked by
Subhomoy Bakshi

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