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Resonance Structure Worksheet

This document discusses resonance structures and how they are used to describe molecules where the bonding cannot be accurately represented by a single Lewis structure. It provides examples of the nitrite (NO2-) and carbonate (CO32-) ions to illustrate how resonance structures average the distribution of electrons between equivalent bonds. The key points are that resonance structures show alternative distributions of electrons that average to describe the actual structure, and experiments support structures where equivalent bonds have identical properties rather than distinct single and double bonds.

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71 views

Resonance Structure Worksheet

This document discusses resonance structures and how they are used to describe molecules where the bonding cannot be accurately represented by a single Lewis structure. It provides examples of the nitrite (NO2-) and carbonate (CO32-) ions to illustrate how resonance structures average the distribution of electrons between equivalent bonds. The key points are that resonance structures show alternative distributions of electrons that average to describe the actual structure, and experiments support structures where equivalent bonds have identical properties rather than distinct single and double bonds.

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hbjvghcg
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© © All Rights Reserved
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Resonance Structure Worksheet 1,2, 3

For many chemical species, a single Lewis structure, consisting of atoms obeying the octet rule,
possibly bearing formal charges, and connected by bonds of positive integer order, is sufficient for
describing the chemical bonding and rationalizing experimentally determined molecular
properties like bond lengths, angles, and dipole moment. However, in some cases, more than one
Lewis structure could be drawn, and experimental properties are inconsistent with any one
structure. In order to address this type of situation, several contributing structures are considered
together as an average, and the molecule is said to be represented by a resonance hybrid in which
several Lewis structures are used collectively to describe its true structure.

Sometimes, even when formal charges are considered, the bonding in some molecules or ions
cannot be described by a single Lewis structure. Resonance is a way of describing delocalized
electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by
a single Lewis formula. A molecule or ion with such delocalized electrons is represented by several
contributing structures (also called resonance structures or canonical forms).

Let’s take a look at nitrite ion, 𝑁𝑂2−

If nitrite ions do indeed contain a single and a double bond, we would expect for the two bond
lengths to be different. A double bond between two atoms is shorter (and stronger) than a single
bond between the same two atoms. Experiments show, however, that both N–O bonds in
NO2− have the same strength and length, and are identical in all other properties.

It is not possible to write a single Lewis structure for NO2− in which nitrogen has an octet and both
bonds are equivalent. Instead, we use the concept of resonance: if two or more Lewis structures
with the same arrangement of atoms can be written for a molecule or ion, the actual distribution
of electrons is an average of that shown by the various Lewis structures. The actual distribution of
electrons in each of the nitrogen-oxygen bonds in NO2− is the average of a double bond and a
single bond. We call the individual Lewis structures resonance forms. The actual electronic
structure of the molecule (the average of the resonance forms) is called a resonance hybrid of the
individual resonance forms. A double-headed arrow between Lewis structures indicates that they
are resonance forms. Thus, the electronic structure of the NO2− ion is shown as:

We should remember that a molecule described as a resonance hybrid never possesses an


electronic structure described by either resonance form. It does not fluctuate between resonance
forms; rather, the actual electronic structure is always the average of that shown by all resonance
forms.
The carbonate anion, CO32−, provides a second example of resonance:

One oxygen atom must have a double bond to carbon to complete the octet on the central atom. All
oxygen atoms, however, are equivalent, and the double bond could form from any one of the three
atoms. This gives rise to three resonance forms of the carbonate ion. Because we can write three
identical resonance structures, we know that the actual arrangement of electrons in the carbonate
ion is the average of the three structures. Again, experiments show that all three C–O bonds are
exactly the same.

Example
1. Draw all possible resonance structures for each of these compounds. Determine the formal
charge on each atom in each of the resonance structures:
(a) O3

(b) SO2

(c) NO2−

(d) NO3−

1. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/02%3A_Polar_Covalent_Bonds%3B_Acids_and_Bases/2.03%3A_Resonance
2. https://en.wikipedia.org/wiki/Resonance_(chemistry)
3. https://opentextbc.ca/chemistry/chapter/7-4-formal-charges-and-resonance/

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