Question icon
Grade 12th passOrganic Chemistry

Which among the given has lowest pKa value :-
1) chloroacetic acid
2) bromoacetic acid
3) nitroacetic acid
4) cyanoacetic acid
Please provide me answer with proper reasoning.I know that stronger acid has lower pKa value but how to determine which one is stronger ?

Profile image of Shivi .
7 Years agoGrade 12th pass
Answers icon

1 Answer

Profile image of Aastha Singh
ApprovedApproved Tutor Answer7 Years ago
Dear student, 
Low pKa means they are asking for stronger acid,
this will work on the principle of conjugate base, the more stronger the acid is, the weaker/stable  is its conjugate base.
here all are electron withdrawing groups which will pull and delocalize the electron of the conjugate base of substituted acetic acid and make it more stable.
 
The electron withdrawing tendecy/ base stabilising tendency/imparting more acidic character tendency are in this order:-
-NO2>-CN>-Cl>-Br