Rank these acids according to their expected pka values. clch2cooh clch2ch2cooh ch3ch2cooh cl2chcooh

Rank these acids according to their expected pka values. clch2cooh clch2ch2cooh ch3ch2cooh cl2chcooh

Answers

CH₃CH₂CH₂COOH > CH₃CH₂COOH > ClCH₂CH₂COOH  > ClCH₂COOH

According to their expected pKa values, the order of those acids should be:

1- Cl2CHCOOH is the strongest acid and the lowest pKa.

2- ClCH2COOH is a strong acid, but no more than the first. Medium pKa value.

3- ClCH2CH2COOH is a strong acid, but no more than the two previous acids. High pKa value.

4- CH3CH2COOH  is the weakest acid, so the highest pKa value.

Explanation:

The pKa values are the negative logarithm of dissociation constant. It represents the relative strengths of the acids. Stronger acids show smaller pKa values and weak acids present larger pKa value. The stronger the acid, the weaker it's the conjugate base. The larger the pKa of the conjugate base, the stronger the acid. The strength of an acid is inversely related to the strength of its conjugate.

Conjugate bases are the substance that has one less proton than the parent acid. The conjugate base of the acid presented in the problem are:

ClCH2COOH -> ClCH2COO-  + H+

ClCH2CH2COOH -> ClCH2CH2COO- + H+

CH3CH2COOH -> CH3CH2COO- + H+

Cl2CHCOOH -> Cl2CHCOO - + H+

Cl2CHCOOH. The negative charge presented on its conjugate base is by resonance and inductive effect. This is the strongest acid.

ClCH2COOH. A negative charge is stabilized by resonance and electron-withdrawing but only one atom is present. So this acid is less strong than the first one.

ClCH2CH2COOH. The negative charge is stabilized by resonance and electron-withdrawing atom but the effect is less compared to the two acids showed previously.

CH3CH2COOH. The negative charge is stabilized by resonance and destabilized due to CH3 group. This is the weakest acid among the problem.

Stronger acids have smaller pKa values and weak acids have larger pKa values. Due to the information present in this problem, Cl2CHCOOH is the strongest acid and the lowest pKa. CH3CH2COOH is the weakest acid, so the highest pKa value.

Finally, we can conclude that according to their expected pKa values, the order of those acids should be:

1- Cl2CHCOOH is the strongest acid and the lowest pKa.

2- ClCH2COOH is a strong acid, but no more than the first. Medium pKa value.

3- ClCH2CH2COOH is a strong acid, but no more than the two previous acids. High pKa value.

4- CH3CH2COOH  is the weakest acid, so the highest pKa value.

CH3CH2COOH< CLCH3CH2COOH<CLCH2COOH<CL2CHCOOH

Explanation:

PKa is the negative logarithm of dissociation constant. It gives the relative strengths of the acids. Stronger acids have smaller pKa values and weak acids have larger pKa value.

The stronger the acid, the weaker its conjugate base. The larger the pKa of the conjugate base, the stronger the acid. The strength of an acid is inversely related to the strength of its conjugate.

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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