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Which acid of each pair shown here would you expect to be stronger?
(i) CH3CO2H or CH2FCO2H
(ii)CH2FCO2H or CH2ClCO2H
(iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H
(iv)
_27-11-08_Utpal_12_Chemistry_12_8_html_m7d7a6d1a.jpg){kind=small}
Asked by Mukesh Last Modified
Answer 
Vishaka Bhutia
Home Tutor
(i)
_27-11-08_Utpal_12_Chemistry_12_8_html_5ae35121.jpg){kind=small}
The +I effect of −CH3 group increases the electron density on the O−H bond. Therefore, release of proton becomes difficult. On the other hand, the −I effect of F decreases the electron density on the O−H bond. Therefore, proton can be released easily. Hence, CH2FCO2H is a stronger acid than CH3CO2H.
(ii)
_27-11-08_Utpal_12_Chemistry_12_8_html_796b09db.jpg){kind=small}
F has stronger −I effect than Cl. Therefore, CH2FCO2H can release proton more easily than CH2ClCO2H. Hence, CH2FCO2H is stronger acid than CH2ClCO2H.
(iii)
_27-11-08_Utpal_12_Chemistry_12_8_html_m241e0508.jpg)
Inductive effect decreases with increase in distance. Hence, the +I effect of F in CH3CHFCH2CO2H is more than it is in CH2FCH2CH2CO2H. Hence, CH3CHFCH2CO2H is stronger acid than CH2FCH2CH2CO2H.
(iv)
_27-11-08_Utpal_12_Chemistry_12_8_html_m3f0466aa.jpg)
Due to the −I effect of F, it is easier to release proton in the case of compound (A). However, in the case of compound (B), release of proton is difficult due to the +I effect of −CH3 group. Hence, (A) is a stronger acid than (B).
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