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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

how to know photocatalytic properties of tio2 nanoparticles...what to do now
Akash Reply
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Maciej
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s. Reply
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Devang Reply
are you nano engineer ?
s.
fullerene is a bucky ball aka Carbon 60 molecule. It was name by the architect Fuller. He design the geodesic dome. it resembles a soccer ball.
Tarell
what is the actual application of fullerenes nowadays?
Damian
That is a great question Damian. best way to answer that question is to Google it. there are hundreds of applications for buck minister fullerenes, from medical to aerospace. you can also find plenty of research papers that will give you great detail on the potential applications of fullerenes.
Tarell
what is the Synthesis, properties,and applications of carbon nano chemistry
Abhijith Reply
Mostly, they use nano carbon for electronics and for materials to be strengthened.
Virgil
is Bucky paper clear?
CYNTHIA
so some one know about replacing silicon atom with phosphorous in semiconductors device?
s. Reply
Yeah, it is a pain to say the least. You basically have to heat the substarte up to around 1000 degrees celcius then pass phosphene gas over top of it, which is explosive and toxic by the way, under very low pressure.
Harper
Do you know which machine is used to that process?
s.
how to fabricate graphene ink ?
SUYASH Reply
for screen printed electrodes ?
SUYASH
What is lattice structure?
s. Reply
of graphene you mean?
Ebrahim
or in general
Ebrahim
in general
s.
Graphene has a hexagonal structure
tahir
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Cied
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Sanket Reply
what's the easiest and fastest way to the synthesize AgNP?
Damian Reply
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Cied
types of nano material
abeetha Reply
I start with an easy one. carbon nanotubes woven into a long filament like a string
Porter
many many of nanotubes
Porter
what is the k.e before it land
Yasmin
what is the function of carbon nanotubes?
Cesar
I'm interested in nanotube
Uday
what is nanomaterials​ and their applications of sensors.
Ramkumar Reply
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what is system testing?
AMJAD
preparation of nanomaterial
Victor Reply
Yes, Nanotechnology has a very fast field of applications and their is always something new to do with it...
Himanshu Reply
good afternoon madam
AMJAD
what is system testing
AMJAD
what is the application of nanotechnology?
Stotaw
In this morden time nanotechnology used in many field . 1-Electronics-manufacturad IC ,RAM,MRAM,solar panel etc 2-Helth and Medical-Nanomedicine,Drug Dilivery for cancer treatment etc 3- Atomobile -MEMS, Coating on car etc. and may other field for details you can check at Google
Azam
anybody can imagine what will be happen after 100 years from now in nano tech world
Prasenjit
after 100 year this will be not nanotechnology maybe this technology name will be change . maybe aftet 100 year . we work on electron lable practically about its properties and behaviour by the different instruments
Azam
name doesn't matter , whatever it will be change... I'm taking about effect on circumstances of the microscopic world
Prasenjit
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Damian
silver nanoparticles could handle the job?
Damian
not now but maybe in future only AgNP maybe any other nanomaterials
Azam
Hello
Uday
I'm interested in Nanotube
Uday
this technology will not going on for the long time , so I'm thinking about femtotechnology 10^-15
Prasenjit
can nanotechnology change the direction of the face of the world
Prasenjit Reply
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
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The eyes of some reptiles are sensitive to 850 nm light. If the minimum energy to trigger the receptor at this wavelength is 3.15 x 10-14 J, what is the minimum number of 850 nm photons that must hit the receptor in order for it to be triggered?
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A teaspoon of the carbohydrate sucrose contains 16 calories, what is the mass of one teaspoo of sucrose if the average number of calories for carbohydrate is 4.1 calories/g?
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4. On the basis of dipole moments and/or hydrogen bonding, explain in a qualitative way the differences in the boiling points of acetone (56.2 °C) and 1-propanol (97.4 °C), which have similar molar masses
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Which of the following will increase the percent of HF that is converted to the fluoride ion in water? (a) addition of NaOH (b) addition of HCl (c) addition of NaF
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Practice Key Terms 5

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Source:  OpenStax, Ut austin - principles of chemistry. OpenStax CNX. Mar 31, 2016 Download for free at http://legacy.cnx.org/content/col11830/1.13
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