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CHAPTER 9
Substitution and Elimination Reactions of Alkyl Halides
Important Terms
b
-elimination reaction
an elimination reaction where the groups being eliminated are bonded to adjacent
or
carbons.
1,2-elimination reaction
anti elimination
an elimination reaction in which the substituents being eliminated are removed
from opposite sides of the molecule.
anti-periplanar
substituents are attached to parallel bonds on opposite sides of a molecule.
aprotic solvent
a solvent that does not have a hydrogen bonded to an oxygen or to a nitrogen;
some aprotic solvents are polar; others are nonpolar.
back-side attack
nucleophilic attack on the side of the carbon opposite the side bonded to the
leaving group.
base
a substance that gains a proton.
basicity
the tendency of a compound to share its electrons with a proton.
bifunctional molecule
a molecule with two functional groups.
bimolecular reaction
a reaction in which two molecules are involved in the transition state of the rate-
determining step.
complete racemization
formation of a pair of enantiomers in equal amounts.
dehydrohalogenation
elimination of a proton and a halide ion.
E1 reaction
a unimolecular elimination reaction.
E2 reaction
a bimolecular elimination reaction.
elimination reaction
a reaction that removes atoms or groups from the reactant to form a
p
bond.
first-order reaction
a reaction whose rate is proportional to the concentration of one reactant.
intermolecular reaction
a reaction that takes place between two molecules.
intimate ion pair
an ion pair that results when the covalent bond that joined the cation and anion has
broken but the cation and anion are still next to each other.
intramolecular reaction
a reaction that takes place within a molecule.