Organic Chemistry

Abhijeet Narang's Avatar
Cool goIITian

Joined: 7 Oct 2011
Post: 93
3 Nov 2011 19:06:29 IST
0 People liked this
6
534 View Post
acidic character
Engineering Entrance , Medical Entrance , NEET , JEE Main , AIIMS , JEE Main & Advanced , Chemistry , Organic Chemistry

which is more acidic and why?phenol or carboxylic acid



Comments (6)


Cool goIITian

Joined: 4 Oct 2009
Posts: 85
3 Nov 2011 19:57:02 IST
0 people liked this

carboxylic acid is more acidic because if we analyze their conjugate bases- in carboxlic acid the -ve charge resides only on O(electronegative element) but in case of phenol the -ve charge resides on C.Hence the resonating structures of phenol are less contributing than the resonating structures of carboxylic acid.

Cool goIITian

Joined: 18 Oct 2011
Posts: 91
4 Nov 2011 08:21:11 IST
0 people liked this

Carboxylic acids are more acidic.Not only it can turn litmus paper but it can also react with carbonates and bicarbonates
RISHABH BAJPAI's Avatar

Scorching goIITian

Joined: 3 Nov 2011
Posts: 233
5 Nov 2011 14:09:17 IST
0 people liked this

Carboxylic acids are more acidic than Phenol...this is attributed to the greater stability of the carboylate ion as compared to the phenoxide ion....(acidity can be judged by the stability of conjugate base formed after removing H+)...In carboylate ion the -ve charge is dispersed on 2 more electro-ve Oxygen atoms as compared to phenoxide in which -ve charge is distributed on 1 electro-ve O and lesser electro-ve carbons...
Madhusudan Chavan's Avatar

Forum Expert
Joined: 9 Mar 2007
Posts: 2821
5 Nov 2011 17:06:45 IST
0 people liked this

Carboxylate ion is more stable than the phenoxide ion as the negative charge is evenly spread on the carboxylate ion,

In case of phenoxide ion, three contributing structures have a negative charge on the less electronegative carbon atom. Therefore their contribution towards the resonance stabilization of the phenoxide ion is very small.

In the carboxylate ion the negative charge is delocalized on the two oxygen atoms, while in phenoxide ion the negative charge remains localized on the oxygen atom only (considering the remaining two contributing structures of the phenoxide ion). Thus carboxylate ion is much more resonance stabilized than the phenoxide ion.Hence release of proton from carboxylic acid is much more easier than phenol.


New kid on the Block

Joined: 5 Nov 2011
Posts: 1
5 Nov 2011 17:29:41 IST
0 people liked this

PHENOL

Abhijeet Narang's Avatar

Cool goIITian

Joined: 7 Oct 2011
Posts: 93
5 Nov 2011 19:28:23 IST
0 people liked this

thnx sir



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