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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Mar 2008 12:26:46 IST
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ARENT ENOLS ALCOHOLS????  THE PRINCIPAL FUNCTIONAL GROUP IS "OL" IT HAS HIGHER PRORITY OVER "ENE" . NOW THE PRINCIPAL FUNCTIONAL GROUP DETERMINES THE PROPERTIES OF THE COMPOUND SO AN ENOL IS EXPECTED TO SHOW PROPERTIES OF ALCOHOLS . I AGREE THERE IS A TAUTOMERIC KETO FORM WHICH IS MORE STABLE BUT THE ENOL FORM TOO EXISTS RIGHT?? SO WONT IT SHOW CHEMICAL PROPERTIES OF ALCOHOLS??????? EG; BROMINE WATER DECOLOURISATION ADDITION OF PCL3 ETC. CAN I SAY AN ENOL IS A TYPE OF ALCOHOL ???????
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21 Mar 2008 12:32:18 IST
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It is not necessary for an enol to show majority percentage of keto form. It depends on which is more stable over the other. Just like phenol exists 99.9% in its enol form. Mostly the compounds show the properties of the dominating form. But if the percentages are close, they should show both.
Anyway, for us we have to determine its property as per structure given.
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21 Mar 2008 12:38:30 IST
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MY QUESTION IS WHETHER AN ENOL IS AN ALCOHOL OR NOT .
THE DOMINATING FORM IS KETO. PLEASE CORRECT ME IF WRONG
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21 Mar 2008 12:47:37 IST
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enol is an alkene which is an alcohol enol = ( alkene + alcohol ) so it would show the properties of alcohol
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21 Mar 2008 14:12:49 IST
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it is almost always true that when we try to make a compound with enol structure , we obtain instead a compound with the keto structure. there is an equilibrium between the two structures but it generally lies very much in favour of keto form.
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Devendra Kumar Shukla
M.Sc physical Chemistry
Currently working in Daswani classes |
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21 Mar 2008 14:34:47 IST
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Two carbonyl groups greatly increase the acidity. For example, 2,4- pentanedione (acetylacetone) has a pK, = 9, which is comparable to the 0-H acidity of phenols . The reason is that the enolate anion has the charge largely shared by the two oxygen atoms . As a result, the enolate anion is stabilized more with respect to the ketone than the enolate anion from 2-propanone is stabilized relative to 2-propanone.
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Devendra Kumar Shukla
M.Sc physical Chemistry
Currently working in Daswani classes |
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21 Mar 2008 14:41:47 IST
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The equilibrium position between a simple ketone and its enol usually lies far on the side of the ketone .However, there are some interesting and important exceptions to this generalization. For instance, the influence of two carbonyl groups on the enol content is very striking, as we can see from the fact that 85% of 2,4-pentanedione is the eno1 form at equilibrium: thats y it SHOWS BROMINE WATER DECOLOURISATION
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Devendra Kumar Shukla
M.Sc physical Chemistry
Currently working in Daswani classes |
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21 Mar 2008 15:00:43 IST
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enol does contain alcohol group and thus will show its properties why that doubt and one more thing always keto form need not dominate take for example phenol in this case for 99.8% enol form only exists as it is aromatic and its keto form is not !!! think about it!!!!
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21 Mar 2008 15:02:04 IST
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even 1,3,5 cyclo hexatrione is a good example it always exists as 1,3,5, phenyl triol!!! think abt this too!!!!
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21 Mar 2008 19:55:54 IST
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EVERYONE ENOLS DO NOT BEHAVE LIKE ALCOHOLS. THERE IS A CHANGE IN THE CHEMICAL ENVIRONMENT .
EXAMPLE TREATMENT WITH SODIUM , THE REACTION IS DIFFERENT FOR KETONES AND ALCOHOLS BUT ENOLS SHOW KETONIC BEHAVIOUR TO ALCOHOLIC .
MY TEACHER WAS IN A HURRY N DIDNOT EXPLAIN HE SIMPLY STATED HE IS TEACHING ORGANIC 4 THE PAST 2 DECADES AT A COACHING CENTER .(BASE)
MY VIEW TO THE QUESTION IS DIFFERENT :-
ASSERTION:
PRINCIPAL FUNCTIONAL GROUP DETERMINES CHEMICAL PROPERTIES OF A COMPOUND .
APPLICATION:
IN ENOLS PRINCIPAL FUNCTIONAL GROUP IS ALCOHOL AS IT HAS HIGHER PRIORITY OVER ENE GROUP SO ITS ENOL'S CHEMICAL PROPERTIES MUST BE DUE TO ITS OL GROUP ??
ELSE THE ASSERTION IS WRONG .
PLEASE HELP ME AND CORRECT ME. THANK YOU
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21 Mar 2008 21:02:33 IST
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i dont get you why??? what happens when enol is treated with Na???? doesnt it form sodium enoxide maybe the proportion is less as maybe in ur case Keto form is more stable BUT TAKE PHENOL WHICH IS AN ENOL DOESNT IT REACT WITH Na?????
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21 Mar 2008 21:11:16 IST
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LOOK DUDE MY SIR TOOK A VERY PECULIAR CASE I THINK 1,3,5 HYDROXY BENZENE N SAID IT WUD RESEMBLE KETONES N NOT OLS
HE WAS IN A HURRY SO HE DIDNT SAY IT CLEARLY
IWILL TRY 2 GET THE ANSWER WITHIN A WEEK SORRY PAL
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COPYRIGHT :
The copyright for the facts written above is held by x4
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21 Mar 2008 21:28:08 IST
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why should 1,3,5 trihydroxy benzene ever behave as a ketone always aromatic nature means extra stability no??? i am sure of it???
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21 Mar 2008 22:03:29 IST
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yeah srini is right...aromaticity inc stability
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