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damaskus [11]
3 years ago
15

Rank these acids according to their expected pKa values.ClCH2COOHClCH2CH2COOHCH3CH2COOHCl2CHCOOHIn order of highest pka to lowes

t pka
Chemistry
2 answers:
Anna007 [38]3 years ago
8 0

Answer: CH₃CH₂CH₂COOH > CH₃CH₂COOH > ClCH₂CH₂COOH  > ClCH₂COOH

Ilia_Sergeevich [38]3 years ago
6 0

Answer:

CH₃CH₂CH₂COOH > CH₃CH₂COOH > ClCH₂CH₂COOH  > ClCH₂COOH

Explanation:

Electron-withdrawing groups (EWGs) increase acidity by inductive removal of electrons from the carboxyl group.

Electron-donating groups (EDGs) decrease acidity by inductive donation of electrons to the carboxyl group.

  • The closer the substituent is to the carboxyl group, the greater is its effect.
  • The more substituents, the greater the effect.  
  • The effect tails off rapidly and is almost zero after about three C-C bonds.

CH₃CH₂-CH₂COOH —  EDG —                         weakest —  pKₐ = 4.82

      CH₃-CH₂COOH — reference —                                     pKₐ = 4.75

  ClCH₂-CH₂COOH — EWG on β-carbon— stronger —     pKₐ = 4.00

           ClCH₂COOH — EWG on α-carbon — strongest —  pKₐ = 2.87

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