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Conjugate acid-base pairs
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How does the concept of conjugate pairs relate to Brønsted-Lowry acids and bases?
They show the
acid-base
transformation
How can the conjugate acid-base pair be interconverted?
To convert the acid to the
conjugate base
, remove
H+
To convert the base to the conjugate acid, add H+
What is the relationship between the conjugate acid-base pairs shown in the image?
H2O
(acid) and
OH-
(conjugate base) form one conjugate acid-base pair
NH3
(base) and
NH4+
(conjugate acid) form the other conjugate acid-base pair
When the acid loses a
proton
(H+), the conjugate base is formed
When the base gains a proton (H+), the conjugate acid is formed
How do the equilibrium reactions differ between the two conjugate acid-base pairs?
For the
H2O
/
OH-
pair: H2O ⇌ H+ + OH-
For the
NH3
/
NH4+
pair: NH3 + H+ ⇌ NH4+
The first is an
autoionization
reaction of water
The second is a
proton transfer
reaction between ammonia and a proton
What is the name of the base in the conjugate acid-base pair shown in the image?
OH-
What are the key differences between the two conjugate acid-base pairs shown?
The first pair involves water (H2O) as the acid and
hydroxide
(OH-) as the base
The second pair involves
ammonia
(NH3) as the base and
ammonium
(NH4+) as the conjugate acid
The first pair involves the removal/addition of a
single
proton
(H+)
The second pair involves the removal/addition of an
entire
ammonium (NH4+) group
How is a conjugate base formed?
When an acid loses a
proton
In the Fischer esterification, what bond breaking occurs?
O-H bond in
carboxylic acid
What is the definition of proton transfer?
A reversible step where a proton
moves
What is a conjugate acid-base pair?
A pair formed by an acid and its
base
How is a conjugate acid formed?
When a
base
gains a
proton
In the reaction
H
C
l
+
HCl +
H
Cl
+
H
2
O
↔
H
3
O
+
H_{2}O \leftrightarrow H_{3}O^ +
H
2
O
↔
H
3
O
+
+
+
+
C
l
−
Cl^ -
C
l
−
, what role does
H
2
O
H_{2}O
H
2
O
play?
H
2
O
H_{2}O
H
2
O
is the
base
What does a proton transfer involve?
A
proton
moves
from one
molecule
to another
How does the proton transfer step affect the reactivity of the molecule?
The proton transfer makes the
carbonyl carbon
more electrophilic
This increases its susceptibility to
nucleophilic attack
This facilitates the formation of the
tetrahedral intermediate
How many bonds are formed and how many bonds are broken in this proton transfer step?
1 bond
formed, 1 bond broken
What is a conjugate acid?
A molecule that has gained a
proton
In the reaction
H
C
l
+
HCl +
H
Cl
+
H
2
O
↔
H
3
O
+
H_{2}O \leftrightarrow H_{3}O^ +
H
2
O
↔
H
3
O
+
+
+
+
C
l
−
Cl^ -
C
l
−
, what role does HCl play?
HCl is the
acid
What is the starting material on the left side of the reaction mechanism?
HO-C-O
What are conjugate pairs in Brønsted-Lowry theory?
Species formed after
proton transfer
Example: HCl becomes
C
l
−
Cl^ -
C
l
−
Example:
H
2
O
H_{2}O
H
2
O
becomes
H
3
O
+
H_{3}O^ +
H
3
O
+
What is the relationship between the conjugate acid-base pairs shown in the image?
H2O (acid) and
OH-
(
conjugate base
) form one conjugate acid-base pair
NH3
(base) and
NH4+
(conjugate acid) form the other conjugate acid-base pair
When the acid loses a
proton
(
H+
), the conjugate base is formed
When the base gains a proton (H+), the conjugate acid is formed
What is a conjugate base?
The original form before
proton
gain
How can the conjugate acid-base pair be interconverted?
To convert the acid to the
conjugate base
, remove
H+
To convert the base to the conjugate acid, add H+
What is a conjugate acid-base pair?
A pair differing by one
H⁺
How do the equilibrium reactions differ between the two conjugate acid-base pairs?
For the
H2O
/
OH-
pair: H2O ⇌ H+ + OH-
For the
NH3
/
NH4+
pair: NH3 + H+ ⇌ NH4+
The first is an
autoionization
reaction of water
The second is a
proton transfer
reaction between ammonia and a proton
What happens to H₂O in the context of conjugate acids and bases?
H₂O acts as an acid
Produces
OH⁻
OH⁻ is its
conjugate base
What are the key differences between the two conjugate acid-base pairs shown?
The first pair involves
water
(H2O) as the acid and
hydroxide
(OH-) as the base
The second pair involves
ammonia
(NH3) as the base and
ammonium
(NH4+) as the conjugate acid
The first pair involves the removal/addition of a
single
proton
(
H+
)
The second pair involves the removal/addition of an
entire
ammonium (NH4+) group
What does a Brønsted-Lowry base do?
Accepts a
proton
If you add H+ to the conjugate base OH-, what is the resulting compound?
H2O
What are the key steps in the process of proton transfer during Fischer esterification?
Proton moves from
carboxylic acid
to
alcohol
O-H bond in carboxylic acid breaks
O-H bond in alcohol forms
Reaction is reversible, indicated by equilibrium arrows
How do you convert between a conjugate acid-base pair?
To convert from acid to
conjugate base
, remove
H+
To convert from base to conjugate acid, add H+
What is the name of the base in the conjugate acid-base pair shown in the image?
NH3
What does a Brønsted-Lowry acid do?
Donates a
proton
What does
H
C
O
3
−
HCO_{3}^{-}
H
C
O
3
−
represent in its conjugate pair?
It is the conjugate base of
carbonic acid
What role does NH₃ play in conjugate acids and bases?
NH₃ acts as a base
Produces
NH₄⁺
NH₄⁺ is its conjugate acid
What is the relationship between the acid and conjugate base in a conjugate acid-base pair?
The acid donates a
proton
(H+) to the base
The base accepts the proton from the acid
This forms the conjugate acid-base pair
How does
H
2
C
O
3
H_{2}CO_{3}
H
2
C
O
3
relate to
H
C
O
3
−
HCO_{3}^{-}
H
C
O
3
−
?
Carbonic acid
is the
conjugate acid
of
bicarbonate
How does the relationship between conjugate acids and bases work?
It is a reversible relationship based on
proton transfer
What does the arrow in conjugate acid-base pairs indicate?
Gain or loss of a
proton
What are the components of the conjugate acid-base pair shown in the image?
H2O
(acid), OH- (
conjugate base
), NH3 (base), NH4+ (conjugate acid)
What are the key differences between the acid-base pair and the conjugate acid-base pair shown in the image?
Acid-base pair:
H2O
(acid),
OH-
(base)
Conjugate acid-base pair: H2O (acid), OH- (conjugate base),
NH3
(base),
NH4+
(conjugate acid)
Acid-base pair involves a direct
proton transfer
Conjugate acid-base pair involves a reversible proton transfer
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