
(a)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(a)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, acetate anion is the weaker acid and equilibrium lies towards the right.
(b)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(b)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, triethylammonium cation is the weaker acid and equilibrium lies towards the right.
(c)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(c)

Explanation of Solution
Given reaction is shown below,
PhC≡CH + NH3 ⇌Phenylacetylene Ammonia
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
PhC≡CH + NH3 ⇀↽ PhC≡C− + NH+4pKa ∼25 pKa 9.26
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, phenyl acetylene is the weaker acid and equilibrium lies towards the left.
(d)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(d)

Explanation of Solution
Given reaction is shown below,
PhC≡CH + iPr2N− Li+ ⇌Phenylacetylene LDA
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
PhC≡CH + iPr2N− Li+ ⇌ PhC≡C− + iPr2NH pKa ∼25 pKa ∼40
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here,
(e)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(e)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, triethylammonium chloride is the weaker acid and equilibrium lies towards the left.
(f)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(f)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, 1-phenyl-2-propanammonium ion is the weaker acid and equilibrium lies towards the right.
(g)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(g)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, amphetamine hydrochloride is the weaker acid and equilibrium lies towards the left.
(h)
Interpretation:
Given acid-base reaction has to be completed and the direction of equilibrium has to be predicted.
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Mixture of acid and base undergoes equilibrium reaction and it’s pka-values determine their direction of reaction.
Weak acids are more stable and less reactive, so equilibrium follows the direction of formation weak acids in a reaction.
Lesser the pka- value of compound will be more acidic. So the equilibrium follows the direction of compounds having low pka-value to the products of high pka value
(h)

Explanation of Solution
Given reaction is shown below,
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base. If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Weak acid is more stable, equilibrium follows the direction of formation weak acids in a reaction. Long arrow indicates the direction where equilibrium favors.
Here, water is the weaker acid and equilibrium lies towards the right.
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Chapter 23 Solutions
Organic Chemistry
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