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Aldehydes Ketones and Carboxylic Acids question

2005 · Shift 0 · Q52
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Aldehydes Ketones and Carboxylic Acids question

2005 · Shift 0 · Q52

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Among the following acids which has the lowest pKa value?
  1. A
    CH3COOHCH_3COOHCH3​COOH
  2. B
    HCOOH
  3. C
    (CH3)2COOH(CH_3)_2COOH(CH3​)2​COOH
  4. D
    CH3CH2COOHCH_3CH_2COOHCH3​CH2​COOH
View written solutionFree

Correct answer: B

  1. We need to identify the acid with the lowest pKapK_apKa​.
    Lower pKapK_apKa​ means stronger acid.

  2. Given acids:

    • A: CH3COOHCH_3COOHCH3​COOH = acetic acid
    • B: HCOOHHCOOHHCOOH = formic acid
    • C: (CH3)2COOH(CH_3)_2COOH(CH3​)2​COOH (intended as a more alkyl-substituted carboxylic acid)
    • D: CH3CH2COOHCH_3CH_2COOHCH3​CH2​COOH = propionic acid
  3. Key principle:
    In carboxylic acids, electron-donating alkyl groups increase electron density on the carboxylate ion and destabilize the conjugate base, making the acid weaker. Hence, more alkyl substitution means higher pKapK_apKa​.

  4. Compare the acids:

    • HCOOHHCOOHHCOOH has no alkyl group attached.
    • CH3COOHCH_3COOHCH3​COOH has one methyl group.
    • CH3CH2COOHCH_3CH_2COOHCH3​CH2​COOH has an ethyl group, which is electron-donating.
    • (CH3)2COOH(CH_3)_2COOH(CH3​)2​COOH is even more alkyl-substituted/electron-donating.

    Therefore, acidity order is approximately: HCOOH>CH3COOH>CH3CH2COOH>(CH3)2COOHHCOOH > CH_3COOH > CH_3CH_2COOH > (CH_3)_2COOHHCOOH>CH3​COOH>CH3​CH2​COOH>(CH3​)2​COOH

    So the corresponding pKapK_apKa​ order is: HCOOH<CH3COOH<CH3CH2COOH<(CH3)2COOHHCOOH < CH_3COOH < CH_3CH_2COOH < (CH_3)_2COOHHCOOH<CH3​COOH<CH3​CH2​COOH<(CH3​)2​COOH

  5. Hence, the lowest pKapK_apKa​ is for HCOOHHCOOHHCOOH.

  6. Option check:

    • A: CH3COOHCH_3COOHCH3​COOH — not lowest
    • B: HCOOHHCOOHHCOOH — lowest pKapK_apKa​
    • C: (CH3)2COOH(CH_3)_2COOH(CH3​)2​COOH — not lowest
    • D: CH3CH2COOHCH_3CH_2COOHCH3​CH2​COOH — not lowest

Final answer: B

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