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If two bonds define two line segments, then they are antiperiplanar if they are
antiparallel in the plane they define. It's much easier to see antiperiplanar
bonds than it is to explain them. In the following diagram, the C-H and C-LG
bonds are antiperiplanar:
E2 reactions require an antiperiplanar β-hydrogen.
Aprotic
A solvent that is not a hydrogen bond donor.
Backside Attack
The SN2 mechanism in which the nucleophile attacks the
α-carbon from a direction directly opposite
to the C-LG bond. Results in inversion of stereochemical configuration.
β-carbon
The carbon(s) adjacent to the α-carbon.
β-elimination
A mechanism that involves the removal of a beta-
hydrogen. All E2 reactions are
β-eliminations.
β-hydrogen
The hydrogen(s) attached to the β-carbon.
Bimolecular
Involving two molecules. In this SparkNote, the term bimolecular is used to
refer to
SN2 and E2 reactions. The rate-limiting transition
states of both
reactions involve two molecules.
Carbocation
A carbon that carries a positive charge. Carbocations are highly unstable and
are prone to
rearrangement. SN1 and E1 reactions proceed through
a common
carbocation intermediate.
Concerted
A single step mechanism. The SN2 and E2 mechanisms are
concerted.
E1
A reaction where a β-hydrogen is Eliminated to form a double
bond.
E1 reactions go through a carbocation intermediate. Somewhat
similar to the
E2 reaction.
E2
An E2 reaction in which a β-hydrogen and a leaving group are
removed to form a double bond. The reaction is so named because it is
bimolecular (2 molecules) and because it involves the Elimination
of a β-hydrogen.
Frontside attack
A disproved SN2 mechanism in which the
nucleophile attacks the α-
carbon from the same side as the C-LG bond. If this
mechanism was valid, it would result in retention of stereochemical
configuration. See backside attack.
Intramolecular
A reaction that involves groups attached to the same molecule. Contrast with
the intermolecular reaction, which takes place between groups on two different
molecules.
Leaving Group
The group that leaves in a substitution or elimination reaction.
Nucleophile
A group characterized by it's SN2 reactivity. Good
nucleophiles tend to be good bases, though they need not be. A nucleophile
has a lone pair of electrons which makes up the business
end of the molecule. See the
nucleophilicity section.
Protic
A solvent that is a hydrogen bond donor.
Rate
The speed of a reaction. Often measured in moles per second.
Rate law
A mathematical equation that relates the rate of a reaction to the concentration
of its reactants. For a generic reaction:
X + Y → Z
The rate law is expressed as:
rate = k [X]a [Y]b
Rate-limiting step
The slowest step in a reaction that determines the overall rate.
Reaction order
In the rate law, the value of "a" and "b" for reactants "X" and "Y,"
respectively. The overall order of a reaction is the sum of "a" and "b" and
tells how many molecules of reactant are involved in the transition state of the
rate-limiting step.
Reaction intermediate
An intermediary molecule that accumulates in negligible quantities during a
reaction.
SN2
A SN2 reaction is a bimolecular (2 molecules) reaction
involving the Substitution of a
Nucleophile for a leaving group. See the SN2
section.
SN1
A reaction in which a Nucleophile Substitutes for a leaving
group.
SN1. It goes through a carbocation intermediate.
Saytzeff's rule
Saytzeff's rule states that an E2 reaction will preferentially form
the most stable alkene isomer. Alkene stability generally increases with
branching at the alkene carbons.
Secondary
A secondary carbon has bonds to two other carbons.
Tertiary
A tertiary carbon has bonds to three other carbons.
Transition state
An extremely unstable molecule that forms between the reactants and their
intermediates/products. A transition state exists at the peaks of an energy
diagram, in contrast to intermediates and products, which form in the troughs.
The âá symbol and brackets denote a transition state structure. The
number of reactant molecules present in the rate-limiting transition state is
equal to the reaction order.
Unimolecular
Involving one molecule. This term is used synonymously with the E1
and SN1 reactions in this SparkNote. The rate-limiting transition
states of both mechanisms involve one molecule.
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