This document provides an overview of acids and bases in organic chemistry. It discusses Brønsted-Lowry acids and bases, where acids are proton donors and bases are proton acceptors. Brønsted-Lowry acid-base reactions involve the transfer of a proton from an acid to a base. It also covers Lewis acids and bases, where acids are electron pair acceptors and bases are electron pair donors. Lewis acid-base reactions involve the donation of an electron pair from a base to an acid. Common examples of Lewis acids are BF3 and AlCl3, which can accept electron pairs. The key concepts are that electron-rich species react with electron-deficient species.
This document provides an overview of acids and bases in organic chemistry. It discusses Brønsted-Lowry acids and bases, where acids are proton donors and bases are proton acceptors. Brønsted-Lowry acid-base reactions involve the transfer of a proton from an acid to a base. It also covers Lewis acids and bases, where acids are electron pair acceptors and bases are electron pair donors. Lewis acid-base reactions involve the donation of an electron pair from a base to an acid. Common examples of Lewis acids are BF3 and AlCl3, which can accept electron pairs. The key concepts are that electron-rich species react with electron-deficient species.
This document provides an overview of acids and bases in organic chemistry. It discusses Brønsted-Lowry acids and bases, where acids are proton donors and bases are proton acceptors. Brønsted-Lowry acid-base reactions involve the transfer of a proton from an acid to a base. It also covers Lewis acids and bases, where acids are electron pair acceptors and bases are electron pair donors. Lewis acid-base reactions involve the donation of an electron pair from a base to an acid. Common examples of Lewis acids are BF3 and AlCl3, which can accept electron pairs. The key concepts are that electron-rich species react with electron-deficient species.
Learning Outcomes At the end of this lecture, students should be able to:
Identify electrophiles and nucleophiles in
organic chemistry reactions
Use concept of acid and base reaction
mechanism to illustrate reaction mechanism
for organic chemistry reactions
5.3.1 Brnsted-Lowry Acids and Bases (Chemistry I )
A Brnsted-Lowry acid is a proton donor.
A Brnsted-Lowry base is a proton acceptor. H+ = proton Examples
5.3.2 Reactions of Brnsted-Lowry Acids and Bases
A Brnsted-Lowry acid base reaction results in the
transfer of a proton from an acid to a base. In an acid-base reaction, one bond is broken, and another one is formed. The electron pair of the base B: forms a new bond to the proton of the acid. The acid HA loses a proton, leaving the electron pair in the HA bond on A.
5.3.2 Reactions of Brnsted-Lowry Acids and Bases
The movement of electrons in reactions can be
illustrated using curved arrow notation. Because two
electron pairs are involved in this reaction, two curved arrows are needed.
Loss of a proton from an acid forms its conjugate base.
Gain of a proton by a base forms its conjugate acid. A double reaction arrow is used between starting
materials and products to indicate that the reaction can
proceed in the forward and reverse directions. These are equilibrium arrows.
5.3.2 Reactions of Brnsted-Lowry Acids and Bases
Examples:
5.3.3 Lewis Acids and Bases
The Lewis definition of acids and bases is more
general than the Brnsted-Lowry definition.
A Lewis acid is an electron pair acceptor.
A Lewis base is an electron pair donor.
5.3.3 Lewis Acids and Bases
Lewis bases are structurally the same as Brnsted-
Lowry bases. Both have an available electron paira
lone pair or an electron pair in a bond. A Brnsted -Lowry base always donates this electron pair to a proton, but a Lewis base donates this electron pair to anything that is electron deficient.
5.3.3 Lewis Acids and Bases
Common examples of Lewis acids (which are not
Brnsted-Lowry acids) include BF3 and AlCl3. These
compounds contain elements in group 3A of the periodic table that cannot accept an electron pair because they do not have filled valence shells of electrons.
5.3.4 Reactions of Lewis Acids and Bases
A Lewis acid must be able to accept an electron
pair, but there are many ways for this to occur.
All Brnsted-Lowry acids are also Lewis acids,
but the reverse is not necessarily true.
Any species that is electron deficient and capable of accepting an electron pair is also a Lewis acid.
5.3.4 Reactions of Lewis Acids and Bases
Any reaction in which one species donates an
electron pair to another species is a Lewis acidbase reaction.
In a Lewis acid-base reaction, a Lewis base
donates an electron pair to a Lewis acid.
Lewis acid-base reactions illustrate a general
pattern in organic chemistry. Electron-rich species react with electron-poor species.
5.3.4 Reactions of Lewis Acids and Bases
In the simplest Lewis acid-base reaction one
bond is formed and no bonds are broken. This
is illustrated in the reaction of BF3 with H2O. H2O donates an electron pair to BF3 to form a new bond.