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ewis Acids and Bases (see Jensen, The Lewis Acid-Base Concepts, Wiley
Interscience, 1980) #
G. N. Lewis (the same chemist who gave us Lewis electrondot structures) proposed a definition of acids and bases at about the same time as
Bronsted, but he included as acids substances that were very different from the
hydrogen-containing Bronsted acids or the acids proposed in earlier definitions.
Lewis noted that there are some compounds that possess no hydrogen, such as BF3,
which have some of the properties historically associated with acids, such as the
ability to change the colors of acid/base indicators. BF3 can also catalyze
reactions that are catalyzed by more familiar acids such as H2SO4, and it will also
combine with bases. The reaction of BF3 with ammonia, for example, is given below.
#
If you compare this process with a typical Bronsted acid/base reaction
involving ammonia (below), certain similarities appear. Note that the base is
behaving the same way in both reactions, by providing an electron pair that forms a
new bond. Lewis focused his attention on the base as an electron-pair donor, and
#suggested that anything that can combine with (accept) this electron pair
should be called an acid. He therefore proposed the following definitions:
base = an electron-pair donor
acid = an electron-pair
acceptor
In a typical Lewis acid/base process, the electron-pair donor and
acceptor simply combine to form a new bond. The result of this combination reaction
is usually called a Lewis adduct. The definitions that would apply to the reaction
of BF3 with NH3 are given below.
#
The substances that are bases
according to the Lewis definition are also Bronsted bases, but Lewis acids can be
very different from traditional acids. The question naturally arose whether or not
a Bronsted acid can also be regarded a Lewis acid. The definition can be expanded
to include Bronsted acids, but there is a difference. Notice that a Bronsted
acid/base reaction is a substitution (displacement) reaction, with the base
(nucleophile) displacing another base (leaving group) when the proton is
transferred (like an SN2 reaction). A Bronsted acid cannot be an electron-pair
acceptor without at the same time disconnecting from an electron pair. Many typical
Lewis acids, on the other hand, simply attach to the base to form the adduct.
Nothing needs to leave.
A more rigorous consideration of Bronsted acids
within the Lewis framework treats the Bronsted acid as a Lewis adduct between H+
and a base. For example, H3O+ is regarded as the adduct of H+ with H2O, and can be
symbolized as A-B. When H3O+ transfers a proton to another base, call it B', the
overall process is represented by B' + A-B ( A-B' + B. It is called an "acid
exchange", and is illustrated below by the protonation of methanol by hydronium
ion.
#
A nucleophilic substitution (SN) reaction can also be regarded as
an acid exchange, as illustrated below, with the substrate treated as a Lewis
adduct between the R group (regarded as R+) and a base (leaving group).
#The Lewis definition can be stretched to the point that it represents one of three
categories into which any chemical reaction can be placed. The other two are
radical reactions and oxidation/reduction reactions. A less familiar definition of
acids and bases by Usanovich even includes oxidation/reduction reactions as
acid/base reactions. Although it can be instructive to see the relationships among
seemingly disparate chemical processes, a definition that is too all-inclusive
loses the advantage of discrimination. In practice, most chemists use the words
acid and base to mean either traditional or Bronsted acids and bases, unless they
have qualified this by specifically using the words Lewis acid or Lewis base.

Examples of Lewis acids. All metal cations can in principle behave as Lewis
acids, as can molecules or ions that have incomplete octets, such as BF3 and AlCl3
and other compounds of boron and aluminum, both of which have only three valence
electrons. A carbocation also has an incomplete octet. Examples of Lewis acid/base
reactions include:
#
#
Molecules with multiple
bonds can function as Lewis acid, illustrated by the reaction of carbon dioxide
with hydroxide ion. # The Lewis definition shares a feature with the Bronsted, in
that a molecule or ion is defined as an acid or base depending on what it is doing
at the time. A molecule might behave as a Lewis acid under one set of
circumstances, and a Lewis base under another. (The carbon dioxide shown above can
behave as a Lewis base by using an unshared electron pair on oxygen to plug into a
Lewis acid.) In addition, the same molecule or ion might behave either as a Lewis
acid or as a Bronsted acid. For example, the carbocation shown above behaving as a
Lewis acid, with water as the Lewis base, can also react as a Bronsted acid with
water as the Bronsted base.
#
Note that the electron pushing shown in all of
the examples in this discussion is not part of the Lewis or Bronsted definitions,
but it helps in understanding the changes that are taking place. Many of the
elementary steps in organic reaction mechanisms are either Bronsted or Lewis
acid/base reactions.
Problems. Complete each of the following, assuming
reaction in a Lewis acid/base sense. Include formal charges. Label each thing in
your equation as either a Lewis acid, Lewis base, or Lewis adduct. Use correct
electron pushing to show the changes taking place. (Answers over.)
#
#
#
###Answers.####
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