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Lewis Acids and Bases

The document discusses the Lewis definition of acids and bases, which is broader than the Brønsted-Lowry definition. It defines Lewis acids as substances that can accept electron pairs from bases, including metal cations and compounds with vacant orbitals. Lewis bases are defined as substances that donate electron pairs, including those with lone pairs. Common examples of Lewis acids and bases are provided, along with diagrams to show electron flow using curved arrows. Noncovalent interactions such as dipole-dipole forces, dispersion forces, and hydrogen bonding are also briefly discussed.

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83 views

Lewis Acids and Bases

The document discusses the Lewis definition of acids and bases, which is broader than the Brønsted-Lowry definition. It defines Lewis acids as substances that can accept electron pairs from bases, including metal cations and compounds with vacant orbitals. Lewis bases are defined as substances that donate electron pairs, including those with lone pairs. Common examples of Lewis acids and bases are provided, along with diagrams to show electron flow using curved arrows. Noncovalent interactions such as dipole-dipole forces, dispersion forces, and hydrogen bonding are also briefly discussed.

Uploaded by

Grad Oana
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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2.

11 Acids and Bases: The Lewis Definition

The Lewis definition is broader than the Brønsted-Lowry definition


Lewis acid – an electrophile
• A substance with a vacant low energy orbital that can accept an
electron pair from a base
• All electrophiles are Lewis acids
Lewis base – a nucleophile
• A substance that donates an electron lone pair to an acid
• All nucleophiles are Lewis bases

Acids and Bases: The Lewis Definition


Lewis Acids and the Curved Arrow Formalism
• To accept an electron pair a Lewis acid must have either:
• A vacant, low-energy orbital
• A polar bond to hydrogen so that it can donate H+

• Various metal cations, such as Mg2+, are Lewis acids


because they accept a pair of electrons when they form a
bond to a base

Acids and Bases: The Lewis Definition


• Compounds of group 3A elements, such as BF 3 and AlCl3
are Lewis acids
• Have unfilled valence orbitals and can accept electron
pairs from Lewis bases
• Many transition metals, such as TiCl4, FeCl3, ZnCl2, and
SnCl4 are Lewis acids
Acids and Bases: The Lewis Definition
Curved arrow formalism
• Indicates the direction of
electron flow from the base to
the acid
• Always means that a pair of
electrons moves from the atom
at the tail of the arrow to the
atom at the head of the arrow
• For the reaction of boron
trifluoride, a Lewis acid, with
dimethyl ether, a Lewis base.
All movement of electrons from
the Lewis base to the Lewis
acid is indicated by a curved
arrow

Acids and Bases: The Lewis Definition


Further examples of Lewis acids

Acids and Bases: The Lewis Definition


Lewis bases
• A compound with a pair of nonbonding electrons that it can
use in bonding to a Lewis acid
• Definition of Lewis base similar to Brønsted-Lowry definition
• H2O acts as a Lewis base
• Has two nonbonding electrons on oxygen
Acids and Bases: The Lewis Definition
• Most oxygen- and nitrogen- containing organic compounds
are Lewis bases
• They have lone pair electrons

Acids and Bases: The Lewis Definition


• Some compounds can act as both acids and bases
• Some compounds have more than one atom with a lone pair
of electrons
• Reaction normally occurs only once in such instances
• The more stable of the two possible protonation products is
formed
• Occurs with carboxylic acids, esters, and amides

Worked Example 2.6


Using Curves Arrows to Show Electron Flow
Using curved arrows, show how acetaldehyde,
CH3CHO, can act as a Lewis base.
2.12 Noncovalent Interactions between
Molecules
Noncovalent Interactions
• Also called intermolecular forces or van der Waals forces
• Types of noncovalent interactions include:
• Dipole-Dipole forces
• Occur between polar molecules as a result of electrostatic
interactions among dipoles
• Forces are either attractive or repulsive

Attractive Repulsive
• Attractive geometry is lower in energy and therefore predominates

Noncovalent Interactions between Molecules


• Dispersion forces
• Attractive dispersion forces in nonpolar molecules are caused by
temporary dipoles
• One side of the molecule may have a slight excess of electrons
relative to the opposite side, giving the molecule a temporary dipole
• Temporary dipole in one molecule causes a nearby molecule to
adopt a temporarily opposite dipole resulting in a small attraction
between the two molecules
• Arise because the electron distribution within molecules is constantly
changing

Noncovalent Interactions between Molecules


• Hydrogen Bonds
• A weak attraction between a hydrogen atom bonded to an
electronegative O or N and an electron lone pair on another O
or N atom
• Strong dipole-dipole interaction involving polarized O-H and
N-H bonds
• Important noncovalent interaction in biological molecules
Noncovalent Interactions between Molecules
• Effects of Hydrogen Bonding
• Causes water to be a liquid rather than a gas at room
temperature
• Holds enzymes in the shapes necessary for catalyzing biological
reactions
• Causes strands of deoxyribonucleic acid (DNA) to pair up and
coil into a double helix

Noncovalent Interactions between Molecules

Hydrophilic (water-loving)
• Dissolves in water
• Table sugar
• Has ionic charges, polar –OH groups, in its structure

Hydrophobic (water-fearing)
• Does not dissolve in water
• Vegetable oil
• Does not have groups that form hydrogen bonds

3.1 Functional Groups


Functional group
• An atom or a group of atoms that is part of a larger molecule
and that has a characteristic chemical reactivity
• Structural features that allow for classification of compounds
into families
Functional Groups

Functional Groups

Functional Groups
Functional Groups

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