Organic Chemistry

New kid on the Block

Joined: 19 Jun 2009
Post: 23
19 Jun 2009 13:48:14 IST
0 People liked this
46
2362 View Post
which is more acidic...................3-fluorophenol or 3-chlorophenol ???
Engineering Entrance , Medical Entrance , NEET , JEE Main , AIIMS , JEE Main & Advanced , Chemistry , Organic Chemistry

which is more acidic...................3-fluorophenol or 3-chlorophenol ???



Comments (46)

dreamer lalit iitr's Avatar

Blazing goIITian

Joined: 18 Feb 2009
Posts: 902
19 Jun 2009 13:49:38 IST
1 people liked this

3-fluoro phenol is more acidic...

New kid on the Block

Joined: 19 Jun 2009
Posts: 23
19 Jun 2009 13:51:51 IST
0 people liked this

reason???
Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:05:38 IST
1 people liked this

According to me its 3-chloro phenol well i applied bent's rule wat u did lalit ?????????
Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:09:28 IST
1 people liked this

Sum1 there to confirm who's right ????????
NugoRama's Avatar

Blazing goIITian

Joined: 11 Mar 2009
Posts: 5567
19 Jun 2009 14:10:11 IST
0 people liked this

The answer is chloro is more acidic than floro ..(confirmed)

dont have the reason at present.

dreamer lalit iitr's Avatar

Blazing goIITian

Joined: 18 Feb 2009
Posts: 902
19 Jun 2009 14:10:26 IST
0 people liked this

the reason is that the resonance effect at the meta position doesnt effect the acidity of the phenol...so all the thing now depends on the -i effect of the halides ,f has more negative i effect so it increases the acidity of the phenol more......@tushar wats the bent rule???
Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:13:06 IST
0 people liked this

Well as the size of fluorine is less than that of chlorine it's lone pair will have greater %s character and hence less tendency to donate LP ......
dreamer lalit iitr's Avatar

Blazing goIITian

Joined: 18 Feb 2009
Posts: 902
19 Jun 2009 14:15:12 IST
1 people liked this

resonance effect will not be counted bcoz the substituent is placed on meta position...
Aakash  Anuj's Avatar

Blazing goIITian

Joined: 26 Mar 2009
Posts: 1428
19 Jun 2009 14:15:54 IST
0 people liked this

3-chlorophenol. In case of 3 flourophenol, there is H-bonding increasing the bond strength to a great extent
taran's Avatar

Blazing goIITian

Joined: 17 Nov 2008
Posts: 1331
19 Jun 2009 14:15:58 IST
0 people liked this

at meta position mesomeric effect is totally absent............so 3-fluorophenol is more acidic 

Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:17:03 IST
0 people liked this

I havent applied resonance i simply follwed one of the applications of bents rule to compare acidic char .........
Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:18:02 IST
0 people liked this

Any expert there to answer this there's a big messup ........
taran's Avatar

Blazing goIITian

Joined: 17 Nov 2008
Posts: 1331
19 Jun 2009 14:20:59 IST
0 people liked this

are bataya toh 3-flurophenol.......meta position pe mesomeric effect is absent.......kya messup?
dibakar_rolles101's Avatar

Cool goIITian

Joined: 18 Mar 2009
Posts: 34
19 Jun 2009 14:23:29 IST
0 people liked this

 Simply make the conjygated bases and check for stability...phenoxide ions are formed....no mesomeric destabilisation ....-i of fluoro greater so more stable c.base HENCE fluoro phenol more acidic..

dibakar_rolles101's Avatar

Cool goIITian

Joined: 18 Mar 2009
Posts: 34
19 Jun 2009 14:24:07 IST
0 people liked this

 H bonding nt effective at meta...

Tushar Sharma's Avatar

Blazing goIITian

Joined: 17 Sep 2008
Posts: 766
19 Jun 2009 14:26:14 IST
0 people liked this

OK OK got your point .........
NugoRama's Avatar

Blazing goIITian

Joined: 11 Mar 2009
Posts: 5567
19 Jun 2009 14:28:12 IST
0 people liked this

Answer is still chloro one ..the order of acidic strength is 3-iodophenol>3-chlorophenol>3-fluorophenol .
dreamer lalit iitr's Avatar

Blazing goIITian

Joined: 18 Feb 2009
Posts: 902
19 Jun 2009 14:28:12 IST
2 people liked this

thats the same thing i stated in my first post.......so rate me
dreamer lalit iitr's Avatar

Blazing goIITian

Joined: 18 Feb 2009
Posts: 902
19 Jun 2009 14:29:21 IST
0 people liked this

we cant take nugo's ans lightly,nugo prove it..



Quick Reply


Reply

Some HTML allowed.
Keep your comments above the belt or risk having them deleted.
Signup for a avatar to have your pictures show up by your comment
If Members see a thread that violates the Posting Rules, bring it to the attention of the Moderator Team
Free Sign Up!
Sponsored Ads

Preparing for JEE?

Kickstart your preparation with new improved study material - Books & Online Test Series for JEE 2014/ 2015


@ INR 5,443/-

For Quick Info

Name

Mobile

E-mail

City

Class

Vertical Limit

Top Contributors
All Time This Month Last Week
1. Bipin Dubey
Altitude - 16545 m
Post - 7958
2. Himanshu
Altitude - 10925 m
Post - 3836
3. Hari Shankar
Altitude - 10085 m
Post - 2217
4. edison
Altitude - 10825 m
Post - 7804
5. Sagar Saxena
Altitude - 8635 m
Post - 8064
6. Yagyadutt Mishr..
Altitude - 6330 m
Post - 1958

Find Posts by Topics

Physics

Topics

Mathematics

Chemistry

Biology

Parents Corner

Board

Fun Zone