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Aldehydes Ketones and Carboxylic Acids question

2011 · Shift 0 · Q14
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Aldehydes Ketones and Carboxylic Acids question

2011 · Shift 0 · Q14

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The strongest acid amongst the following compounds is :
  1. A
    HCOOH
  2. B
    CH3CH2CH(Cl)CO2HCH_3CH_2CH(Cl)CO_2HCH3​CH2​CH(Cl)CO2​H
  3. C
    ClCH2CH2CH2COOHClCH_2CH_2CH_2COOHClCH2​CH2​CH2​COOH
  4. D
    CH3COOHCH_3COOHCH3​COOH
View written solutionFree

Correct answer: B

  1. Principle involved

    The acidity of carboxylic acids depends on the stability of the conjugate base, RCOO−RCOO^-RCOO−.
    Electron-withdrawing groups increase acidity by stabilizing the negative charge through the −I-I−I effect.

  2. Compare the given acids

    Option A: HCOOHHCOOHHCOOH

    Formic acid has no alkyl group attached. It is more acidic than simple alkyl carboxylic acids like acetic acid because there is no electron-donating alkyl group.

    Option D: CH3COOHCH_3COOHCH3​COOH

    Acetic acid has a methyl group, which shows a +I+I+I effect and decreases acidity compared to formic acid.

    Therefore, HCOOH>CH3COOHHCOOH > CH_3COOHHCOOH>CH3​COOH

  3. Effect of chlorine substituent

    Chlorine is strongly electron-withdrawing by the −I-I−I effect, so chloro-substituted carboxylic acids are more acidic than unsubstituted ones.

    The strength of the −I-I−I effect decreases with distance from the COOHCOOHCOOH group.

    Option B: CH3CH2CH(Cl)CO2HCH_3CH_2CH(Cl)CO_2HCH3​CH2​CH(Cl)CO2​H

    Here, Cl is on the α\alphaα-carbon (adjacent to COOHCOOHCOOH). So its −I-I−I effect is very strong.

    Option C: ClCH2CH2CH2COOHClCH_2CH_2CH_2COOHClCH2​CH2​CH2​COOH

    Here, Cl is on the γ\gammaγ-carbon (farther from COOHCOOHCOOH). So its −I-I−I effect is much weaker.

    Hence, CH3CH2CH(Cl)CO2H>ClCH2CH2CH2COOHCH_3CH_2CH(Cl)CO_2H > ClCH_2CH_2CH_2COOHCH3​CH2​CH(Cl)CO2​H>ClCH2​CH2​CH2​COOH

  4. Overall acidity order

    Combining all effects: CH3CH2CH(Cl)CO2H>ClCH2CH2CH2COOH>HCOOH>CH3COOHCH_3CH_2CH(Cl)CO_2H > ClCH_2CH_2CH_2COOH > HCOOH > CH_3COOHCH3​CH2​CH(Cl)CO2​H>ClCH2​CH2​CH2​COOH>HCOOH>CH3​COOH

  5. Conclusion

    The strongest acid is: CH3CH2CH(Cl)CO2H\boxed{CH_3CH_2CH(Cl)CO_2H}CH3​CH2​CH(Cl)CO2​H​ So, the correct option is B.

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