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Pyridine can be modified by attaching different groups on the asterisk. As a result of this, some properties of the compound may vary. One property that is affected is the acidity of the conjugate bases. The acid dissociation constants of the conjugate acids are given in the table below.

 

Group Substituted in Asterisk Ka of Conjugate Acid
NO2  
Cl  
H  
CH3  

 

Suppose each conjugate acid is dissolved in water to yield a 0.050 M solution. Which solution would have the highest pH?

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Brian Hingpit
Brian HingpitLv10
4 Nov 2020

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Related questions

A hydrogen atom in the organic base pyridine, , can be substituted by various atoms or groups to give , where X is an atom such as Cl or a group such as . The following table gives Ka values for the conjugate acids of a variety of substituted pyridines.

Atom or Group X Ka of Conjugate Acid
   
Cl  
H  
   

 

(a) Suppose each conjugate acid is dissolved in sufficient water to give a 0.050 M solution. Wich solution would have the highest pH? The lowest pH?

(b) Which of the substituted pyridines is the strongest Bronsted base? Which is the weakest Bronsted base?

A hydrogen atom in the organic base pyridine, C5H5N, can be substituted by various atoms or groups to give XC5H4N, where X is an atom such as Cl or a group such as CH3. The following table gives Ka values for the conjugate acids of a variety of substituted pyridines.

(a) Suppose each conjugate acid is dissolved in sufficient water to give a 0.050 M solution. Which solution would have the highest pH? The lowest pH?

(b) Which of the substituted pyridines is the strongest Brønsted base? Which is the weakest Brønsted base?

A hydrogen atom in the organic base pyridine, C5H5N, can be substituted by various atoms or groups to give XC5H4N, where X is an atom such as Cl or a group such as CH3. The following table gives Ka values for the conjugate acids of a variety of substituted pyridines.

(a) Suppose each conjugate acid is dissolved in sufficient water to give a 0.050 M solution. Which solution would have the highest pH? The lowest pH?

(b) Which of the substituted pyridines is the strongest Bronsted base? Which is the weakest Bronsted base?

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