|
Substitution versus Elimination |
Chapter 8: Nucleophilic Substitution |
Substitution and elimination
reactions are strongly influenced by many factors. Some of the more important
factors are outlined in the following table.
The significance of the effect is stated first, then the system that will favor
the reaction is stated.
This should help you deal with the questions....
1. When does an anion function as a Nu and when does it function as a B ?, and
therefore,
2. When to I get substitution and when do I get elimination ?
|
|
|
|
|
|
Typical Conditions |
|
|
Polar solvents |
Good Nu and weak base |
Good LG |
3o or resonance stabilized |
AgNO3 / aq. EtOH |
|
|
Polar aprotic solvents |
Good Nu and weak base |
Good LG |
Methyl or 1o |
NaI / Acetone |
|
|
Polar solvents |
Weak base |
Good LG |
3o or resonance stabilized |
H2SO4, heat |
|
|
Polar aprotic solvents |
Poor Nu and strong base |
Good LG |
3o |
KOH, heat, |