__ has little effect on __ because __ invovles attack on an unhindered proton.
When a __ attacks a carbon atom, however, a bulky __ cannot approach the C atom so easily. Most __ are also __, capable of attacking either a proton or an electrophilic carbon atom.
If we want a species to act as a base, what do we do?
If we want a species to act as a nucleophile, what do we do?
- steric hindrance
- basicity x2
- nucleophile x2
- use a bulky reagent
- use a less hindered reagent