page 21 Flashcards
Role of the Leaving Group:
In nucleophilic substitution reactions (R−X+Nu−), the leaving group departs, taking the electron pair from the
C−X bond.
A good leaving group ensures the reaction proceeds efficiently.
Stability of the Leaving Group:
The better the leaving group, the more stable it is after departure.
Stability is influenced by how well the group can accommodate the negative charge.
Relation to Base Strength:
Weak bases are better leaving groups.
Example:
H2O is a better leaving group than
OH−because it is a weaker base.
Examples of Good Leaving Groups:
Halide ions:
I −>Br −>Cl −>F −
(based on increasing stability as bases weaken).
Neutral molecules:
H2O is better than
HO−.
Question: What happens to the leaving group during nucleophilic substitution?
Answer: It departs with the electron pair from the
C−X bond, forming
X −.
Why is a weaker base a better leaving group?
Answer: Weaker bases are more stable, making them better at accommodating the negative charge.
Which is a better leaving group:
Br− or
Cl−?
Answer:
Br−, because it is a weaker base and more stable.
Why is
H2O a better leaving group than
OH−?
Answer:
H2O is a weaker base and more stable after leaving.
Question: Rank
F
−
F
−
,
C
l
−
Cl
−
,
B
r
−
Br
−
, and
I
−
I
−
in order of leaving group ability.
Answer:
I
−
>
B
r
−
>
C
l
−
>
F
−
I
−
>Br
−
>Cl −>F −
.
Question: Is
N
H
3
NH
3
a better leaving group than
O
H
−
OH
−
?
Answer: Yes, because
N
H
3
NH
3
is a weaker base than
O
H
−
OH
−
.