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Key concepts and summary

In a Lewis structure, formal charges can be assigned to each atom by treating each bond as if one-half of the electrons are assigned to each atom. These hypothetical formal charges are a guide to determining the most appropriate Lewis structure. A structure in which the formal charges are as close to zero as possible is preferred. Resonance occurs in cases where two or more Lewis structures with identical arrangements of atoms but different distributions of electrons can be written. The actual distribution of electrons (the resonance hybrid) is an average of the distribution indicated by the individual Lewis structures (the resonance forms).

Key equations

  • formal charge = # valence shell electrons (free atom) # one pair electrons 1 2 # bonding electrons

Chemistry end of chapter exercises

Write resonance forms that describe the distribution of electrons in each of these molecules or ions.

(a) selenium dioxide, OSeO

(b) nitrate ion, NO 3

(c) nitric acid, HNO 3 (N is bonded to an OH group and two O atoms)

(d) benzene, C 6 H 6 :

A Lewis structure shows a hexagonal ring composed of six carbon atoms. They form single bonds to each another and single bonds to one hydrogen atom each.

(e) the formate ion:

A Lewis structure shows a carbon atom single bonded to two oxygen atoms and a hydrogen atom. The structure is surrounded by brackets and there is a superscripted negative sign.
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Write resonance forms that describe the distribution of electrons in each of these molecules or ions.

(a) sulfur dioxide, SO 2

(b) carbonate ion, CO 3 2−

(c) hydrogen carbonate ion, HCO 3 (C is bonded to an OH group and two O atoms)

(d) pyridine:

A Lewis structure depicts a hexagonal ring composed of five carbon atoms and one nitrogen atom. Each carbon atom is single bonded to a hydrogen atom.

(e) the allyl ion:

A Lewis structure shows a carbon atom single bonded to two hydrogen atoms and a second carbon atom. The second carbon atom is single bonded to a hydrogen atom and a third carbon atom. The third carbon atom is single bonded to two hydrogen atoms. The whole structure is surrounded by brackets, and there is a superscripted negative sign.

(a)
Two Lewis structures are shown with a double-headed arrow in between. The left structure shows a sulfur atom with a lone pair of electrons single bonded to the left to an oxygen atom with three lone pairs of electrons. The sulfur atom is also double bonded on the right to an oxygen atom with two lone pairs of electrons. The right structure depicts the same atoms, but this time the double bond is between the left oxygen and the sulfur atom. The lone pairs of electrons have also shifted to account for the change of bond types. The sulfur atom in the right structures, also has a third electron dot below it. ;
(b)
Three Lewis structures are shown, with double-headed arrows in between, each surrounded by brackets and a superscripted two negative sign. The left structure depicts a carbon atom bonded to three oxygen atoms. It is single bonded to two of these oxygen atoms, each of which has three lone pairs of electrons, and double bonded to the third, which has two lone pairs of electrons. The double bond is located between the bottom oxygen and the carbon. The central and right structures are the same as the first, but the position of the double bonded oxygen has moved to the left oxygen in the right structure while the central structure only has single bonds. The lone pairs of electrons change to correspond with the bonds as well. ;
(c)
Two Lewis structures are shown, with a double-headed arrow in between, each surrounded by brackets and a superscripted negative sign. The left structure depicts a carbon atom bonded to three oxygen atoms. It is single bonded to one of these oxygen atoms, which has three lone pairs of electrons, and double bonded to the other two, which have two lone pairs of electrons. One of the double bonded oxygen atoms also has a single bond to a hydrogen atom. The right structure is the same as the first, but there is only one double bonded oxygen. The oxygen with the single bonded hydrogen now has a single bond to the carbon atom. The lone pairs of electrons have also changed to correspond with the bonds. ;
(d)
Two Lewis structures are shown with a double-headed arrow in between. The left structure depicts a hexagonal ring composed of five carbon atoms, each single bonded to a hydrogen atom, and one nitrogen atom that has a lone pair of electrons. The ring has alternating single and double bonds. The right structure is the same as the first, but each double bond has rotated to a new position. ;
(e)
Two Lewis structures are shown with a double-headed arrow in between. The left structure shows a carbon atom single bonded to two hydrogen atoms and a second carbon atom. The second carbon atom is single bonded to a hydrogen atom and double bonded to a third carbon atom. The third carbon atom is single bonded to two hydrogen atoms. The whole structure is surrounded by brackets and a superscripted negative sign. The right structure shows a carbon atom single bonded to two hydrogen atoms and double bonded to a second carbon atom. The second carbon atom is single bonded to a hydrogen atom and a third carbon atom. The third carbon atom is single bonded to two hydrogen atoms. The whole structure is surrounded by brackets and a superscripted negative sign.

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Write the resonance forms of ozone, O 3 , the component of the upper atmosphere that protects the Earth from ultraviolet radiation.

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Sodium nitrite, which has been used to preserve bacon and other meats, is an ionic compound. Write the resonance forms of the nitrite ion, NO 2 .

 
Two pairs of Lewis structures are shown with a double-headed arrow in between each pair. The left structure of the first pair shows a nitrogen atom with one lone pair of electrons single bonded to an oxygen atom with three lone pairs of electrons. It is also double bonded to an oxygen with two lone pairs of electrons. The right image of this pair depicts the mirror image of the left. Both images are surrounded by brackets and a superscripted negative sign. They are labeled, “For N O subscript two superscript negative sign.” The left structure of the second pair shows an oxygen atom with one lone pair of electrons single bonded to an oxygen atom with three lone pairs of electrons. It is also double bonded to an oxygen atom with two lone pairs of electrons. The right structure appears as a mirror image of the left. These structures are labeled, “For O subscript three.”

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In terms of the bonds present, explain why acetic acid, CH 3 CO 2 H, contains two distinct types of carbon-oxygen bonds, whereas the acetate ion, formed by loss of a hydrogen ion from acetic acid, only contains one type of carbon-oxygen bond. The skeleton structures of these species are shown:

Two Lewis structures are shown with a double headed arrow in between. The left structure shows a carbon atom single bonded to three hydrogen atoms and a second carbon atom. The second carbon is single bonded to two oxygen atoms. One of the oxygen atoms is single bonded to a hydrogen atom. The right structure, surrounded by brackets and with a superscripted negative sign, depicts a carbon atom single bonded to three hydrogen atoms and a second carbon atom. The second carbon atom is single bonded to two oxygen atoms.
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Write the Lewis structures for the following, and include resonance structures where appropriate. Indicate which has the strongest carbon-oxygen bond.

(a) CO 2

(b) CO

(a)
This structure shows a carbon atom double bonded to two oxygen atoms, each of which has two lone pairs of electrons.
(b)
The right structure of this pair shows a carbon atom with one lone pair of electrons triple bonded to an oxygen with one lone pair of electrons.
CO has the strongest carbon-oxygen bond because there is a triple bond joining C and O. CO 2 has double bonds.

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Toothpastes containing sodium hydrogen carbonate (sodium bicarbonate) and hydrogen peroxide are widely used. Write Lewis structures for the hydrogen carbonate ion and hydrogen peroxide molecule, with resonance forms where appropriate.

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Determine the formal charge of each element in the following:

(a) HCl

(b) CF 4

(c) PCl 3

(d) PF 5

(a) H: 0, Cl: 0; (b) C: 0, F: 0; (c) P: 0, Cl 0; (d) P: 0, F: 0

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Determine the formal charge of each element in the following:

(a) H 3 O +

(b) SO 4 2−

(c) NH 3

(d) O 2 2−

(e) H 2 O 2

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Calculate the formal charge of chlorine in the molecules Cl 2 , BeCl 2 , and ClF 5 .

Cl in Cl 2 : 0; Cl in BeCl 2 : 0; Cl in ClF 5 : 0

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Calculate the formal charge of each element in the following compounds and ions:

(a) F 2 CO

(b) NO

(c) BF 4

(d) SnCl 3

(e) H 2 CCH 2

(f) ClF 3

(g) SeF 6

(h) PO 4 3−

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Draw all possible resonance structures for each of these compounds. Determine the formal charge on each atom in each of the resonance structures:

(a) O 3

(b) SO 2

(c) NO 2

(d) NO 3

(a)
Two Lewis structures are shown with a double-headed arrow in between. The left structure shows an oxygen atom with one lone pair of electrons single bonded to an oxygen atom with three lone pairs of electrons. It is also double bonded to an oxygen atom with two lone pairs of electrons. The symbols and numbers below this structure read, “( 0 ), ( positive 1 ), ( negative 1 ).” The phrase, “Formal charge,” and a right-facing arrow lie to the left of this structure. The right structure appears as a mirror image of the left and the symbols and numbers below this structure read, “( negative 1 ), ( positive 1 ), ( 0 ).” ;
(b)
Two Lewis structures are shown, with a double-headed arrow in between. The left structure shows a sulfur atom with one lone pair of electrons single bonded to an oxygen atom with three lone pairs of electrons. The sulfur atom also double bonded to an oxygen atom with two lone pairs of electrons. The symbols and numbers below this structure read, “( negative 1 ), ( positive 1 ), ( 0 ).” The right structure appears as a mirror image of the left and the symbols and numbers below this structure read, “( 0 ), ( positive 1 ), ( negative 1 ).” ;
(c)
[Two Lewis structures are shown, with brackets surrounding each with a superscripted negative sign and a double ended arrow in between. The left structure shows a nitrogen atom with one lone pair of electrons single bonded to an oxygen atom with three lone pairs of electrons and double bonded to an oxygen atom with two lone pairs of electrons. The symbols and numbers below this structure read “open parenthesis, 0, close parenthesis, open parenthesis, 0, close parenthesis, open parenthesis, negative 1, close parenthesis. The right structure appears as a mirror image of the left and the symbols and numbers below this structure read “open parenthesis, negative 1, close parenthesis, open parenthesis, 0, close parenthesis, open parenthesis, 0, close parenthesis.] ;
(d)
[Three Lewis structures are shown, with brackets surrounding each with a superscripted negative sign and a double ended arrow in between. The left structure shows a nitrogen atom single bonded to two oxygen atoms, each with three lone pairs of electrons and double bonded to an oxygen atom with two lone pairs of electrons. The single bonded oxygen atoms are labeled, from the top of the structure and going clockwise, “open parenthesis, negative 1, close parenthesis, open parenthesis, positive 1, close parenthesis”. The symbols and numbers below this structure read “open parenthesis, 0, close parenthesis, open parenthesis, negative 1, close parenthesis. The middle structure shows a nitrogen atom single bonded to two oxygen atoms, each with three lone pairs of electrons, one of which is labeled “open parenthesis, positive 1, close parenthesis” and double bonded to an oxygen atom with two lone pairs of electrons labeled “open parenthesis, 0, close parenthesis”. The symbols and numbers below this structure read “open parenthesis, negative 1, close parenthesis, open parenthesis, negative 1, close parenthesis. The right structure shows a nitrogen atom single bonded to two oxygen atoms, each with three lone pairs of electrons and double bonded to an oxygen atom with two lone pairs of electrons. One of the single bonded oxygen atoms is labeled, “open parenthesis, negative 1, close parenthesis while the double bonded oxygen is labeled, “open parenthesis, positive 1, close parenthesis”. The symbols and numbers below this structure read “open parenthesis, negative 1, close parenthesis” and “open parenthesis, 0, close parenthesis”.]

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Based on formal charge considerations, which of the following would likely be the correct arrangement of atoms in nitrosyl chloride: ClNO or ClON?

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Based on formal charge considerations, which of the following would likely be the correct arrangement of atoms in hypochlorous acid: HOCl or OClH?

HOCl

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Based on formal charge considerations, which of the following would likely be the correct arrangement of atoms in sulfur dioxide: OSO or SOO?

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Draw the structure of hydroxylamine, H 3 NO, and assign formal charges; look up the structure. Is the actual structure consistent with the formal charges?

The structure that gives zero formal charges is consistent with the actual structure:
A Lewis structure shows a nitrogen atom with one lone pair of electrons single bonded to two hydrogen atoms and an oxygen atom which has two lone pairs of electrons. The oxygen atom is single bonded to a hydrogen atom.

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Iodine forms a series of fluorides (listed here). Write Lewis structures for each of the four compounds and determine the formal charge of the iodine atom in each molecule:

(a) IF

(b) IF 3

(c) IF 5

(d) IF 7

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Write the Lewis structure and chemical formula of the compound with a molar mass of about 70 g/mol that contains 19.7% nitrogen and 80.3% fluorine by mass, and determine the formal charge of the atoms in this compound.

NF 3 ;
A Lewis structure shows a nitrogen atom with one lone pair of electrons single bonded to three fluorine atoms, each with three lone pairs of electrons.

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Which of the following structures would we expect for nitrous acid? Determine the formal charges:

Two Lewis structures are shown, with the word “or” in between. The left structure shows a nitrogen atom single bonded to an oxygen atom with three lone pairs of electrons. It is also single bonded to a hydrogen atom and double bonded to an oxygen atom with two lone pairs of electrons. The right structure shows a hydrogen atom single bonded to an oxygen atom with two lone pairs of electrons. The oxygen atom is single bonded to a nitrogen atom which is double bonded to an oxygen atom with two lone pairs of electrons.
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Sulfuric acid is the industrial chemical produced in greatest quantity worldwide. About 90 billion pounds are produced each year in the United States alone. Write the Lewis structure for sulfuric acid, H 2 SO 4 , which has two oxygen atoms and two OH groups bonded to the sulfur.

 
A Lewis structure shows a hydrogen atom single bonded to an oxygen atom with two lone pairs of electrons. The oxygen atom is single bonded to a sulfur atom. The sulfur atom is double bonded to two oxygen atoms, each of which have three lone pairs of electrons, and single bonded to an oxygen atom with two lone pairs of electrons. This oxygen atom is single bonded to a hydrogen atom.

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Questions & Answers

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Practice Key Terms 5

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Source:  OpenStax, Chemistry. OpenStax CNX. May 20, 2015 Download for free at http://legacy.cnx.org/content/col11760/1.9
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