page 46 Flashcards
What type of attack is characteristic of
S
N
2
S
N
2 reactions?
A: Backside attack.
What happens to the configuration at a stereogenic center in
S
N
2
S
N
2 reactions?
A: It undergoes inversion of configuration.
Why does inversion of configuration occur in
S
N
2
S
N
2 reactions?
A: The nucleophile attacks from the opposite side of the leaving group, displacing it.
What is the relationship between the bond to the nucleophile in the product and the bond to the leaving group in the starting material?
A: They are on opposite sides of the molecule.
What does the term “inversion of configuration” mean in
S
N
2
S
N
2 reactions?
A: The spatial arrangement of substituents around the carbon atom is reversed.
How does inversion in
S
N
2
S
N
2 reactions affect the stereochemistry of the product?
A: The stereochemistry of the product is opposite to that of the reactant.
What does backside attack ensure in an
S
N
2
S
N
2 reaction?
A: It minimizes electronic repulsion between the nucleophile and the leaving group.
Which type of carbon is most likely to exhibit inversion in
S
N
2
S
N
2 reactions?
A: A stereogenic carbon (a carbon bonded to four different groups).
What happens if the carbon in the
S
N
2
S
N
2 reaction is not a stereogenic center?
A: No inversion of configuration is observed because there is no chirality.
In
S
N
2
S
N
2 reactions, what is the fate of the leaving group after inversion?
A: It is displaced by the nucleophile and exits as a free ion.
