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Chemistry: The Molecular Science

John W. Moore, Conrad L. Stanitski, Peter C. Jurs

Chapter 8

Covalent Bonding - all with Video Answers

Educators


Chapter Questions

01:14

Problem 1

Explain the difference between an ionic bond and a cova-
lent bond.

Emily Himsel
Emily Himsel
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01:15

Problem 2

What kind of bonding (ionic or covalent) would you predict for the products resulting from the following combinations of elements?
(a) $\mathrm{Na}+\mathrm{I}_{2}$
(b) $\mathrm{C}+\mathrm{S}$
(c) $\mathrm{Mg}+\mathrm{Br}_{2}$
(d) $\mathrm{P}_{4}+\mathrm{Cl}_{2}$

Emily Himsel
Emily Himsel
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01:34

Problem 3

What characteristics must atoms $A$ and $X$ have if they are able to form a covalent bond $A-X$ with each other? A polar covalent bond with each other?

Lottie Adams
Lottie Adams
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01:01

Problem 4

Indicate the difference among alkanes, alkenes, and alkynes by giving the structural formula of a compound in each class that contains three carbon atoms.

Emily Himsel
Emily Himsel
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02:15

Problem 5

Refer to Table $8.3$ and answer these questions:
(a) Do any molecules with more than eight electrons have a second-period element as the central atom?
(b) What is the maximum number of bond pairs and lone pairs that surround the central atom in any of these molecules?

Natalie Johns
Natalie Johns
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01:00

Problem 6

While sulfur forms the compounds $\mathrm{SF}_{4}$ and $\mathrm{SF}_{6}$, no equivalent compounds of oxygen, OF, and OF , are known. Explain.

Emily Himsel
Emily Himsel
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01:36

Problem 7

Which of these molecules have an odd number of valence
electrons: $\mathrm{NO}_{2}, \mathrm{SCL}, \mathrm{NH}_{2}, \mathrm{NO}_{z}$ ?

Emily Himsel
Emily Himsel
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01:23

Problem 8

Write resonance structures for $\mathrm{NO}_{2}^{-}$. Predict a value for the N-O bond length based on bond lengths given in Table 8.1, and explain your answer.

Lottie Adams
Lottie Adams
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02:18

Problem 9

Consider these structures for the formate ion, $\mathrm{HCO}_{2}^{-} .$ Designate which two are resonance structures and which is equivalent to one of the resonance structures.

Lottie Adams
Lottie Adams
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01:56

Problem 10

Consider a series of molecules in which the $\mathrm{C}$ atom is bonded to atoms of second-period elements: $\mathrm{C}-\mathrm{O}, \mathrm{C}-\mathrm{F}$, $\mathrm{C}-\mathrm{N}, \mathrm{C}-\mathrm{C}$, and $\mathrm{C}-\mathrm{B} .$ Place these bonds in order of
increasing bond length.

Lottie Adams
Lottie Adams
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01:16

Problem 11

What are the trends in bond length and bond energy for a series of related bonds-for instance, single, double, and
triple carbon-to-oxygen bonds?

Lottie Adams
Lottie Adams
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02:12

Problem 12

Why is cis-trans isomerism not possible for alkynes?

Lottie Adams
Lottie Adams
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02:11

Problem 13

Write the Lewis structures of (a) dichlorine monoxide,
$\mathrm{Cl}_{2} \mathrm{O} ;$
(b) hydrogen peroxide, $\mathrm{H}_{2} \mathrm{O}_{2} ;$ (c) borohydride ion, $\mathrm{BH}_{4}^{-} ;$ (d) phosphonium ion, $\mathrm{PH}_{4}^{+}$; and (e) $\mathrm{PCl}_{5}$.

Lottie Adams
Lottie Adams
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02:17

Problem 14

Write Lewis structures for these molecules or ions.
(a) CIF
(b) H,Se
(c) $\mathrm{BF}_{-}$
(d) $\mathrm{PO}_{4}^{3}$

Emily Himsel
Emily Himsel
Numerade Educator
01:50

Problem 15

Write Lewis structures for these molecules.
(a) CHCIF $_{2}$, one of several chlorofluorocarbons that has been used in refrigeration
(b) Methyl alcohol, $\mathrm{CH}_{3} \mathrm{OH}$
(c) Methyl amine, $\mathrm{CH}_{3} \mathrm{NH}$,

Emily Himsel
Emily Himsel
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02:57

Problem 16

Write Lewis structures for these molecules or ions.
(a) $\mathrm{CH}_{3} \mathrm{C}$
(b) $\mathrm{SiO}_{i}^{4-}$
(c) CIF
(d) $\mathrm{C}_{2} \mathrm{H}_{6}$

Natalie Johns
Natalie Johns
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01:17

Problem 17

Write Lewis structures for these molecules.
(a) Formic acid, $\mathrm{HCOOH}$, in which atomic arrangement is
(b) Acetonitrile, $\mathrm{CH}_{3} \mathrm{CN}$
(c) Vinyl chloride, $\mathrm{CH}_{2} \mathrm{CHCl}$, the molecule from which PVC plastics are made

Lottie Adams
Lottie Adams
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01:17

Problem 18

Write Lewis structures for these molecules.
(a) Tetrafluoroethylene, $\mathrm{C}_{2} \mathrm{~F}_{4}$, the molecule from which Teflon is made
(b) Acrylonitrile, $\mathrm{CH}_{2} \mathrm{CHCN}$, the molecule from which Orlon is made

Lottie Adams
Lottie Adams
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08:54

Problem 19

Write Lewis structures for:
(a) $\mathrm{N}_{2}^{+}$
(b) $\mathrm{XeF}_{7}^{-}$
(c) tetracyanoethane, $\mathrm{C}_{6} \mathrm{~N}_{4}$

Sandra Lundell
Sandra Lundell
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01:20

Problem 20

Write Lewis structures for:
(a) Disulfur dichloride, $\mathrm{S}_{2} \mathrm{Cl}_{2}$
(b) Nitrous acid, HNO $_{2}$, which has no oxygen-to-oxygen bonds
(c) CIF $_{6}^{+}$

Lottie Adams
Lottie Adams
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03:32

Problem 21

Which of these are correct Lewis structures and which are incorrect? Explain what is wrong with the incorrect ones.
(a) $: \mathrm{N}=\ddot{\mathrm{N}}^{\prime}$
(b) $\mathbf{N}_{2}$
$\mathrm{NCl}_{3}$
(c)
(d)
<smiles>[O-]</smiles> $\left(\mathrm{CH}_{5}\right)_{2} \mathrm{O}$

Natalie Johns
Natalie Johns
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10:07

Problem 22

Which of these are correct Lewis structures and which are incorrect? Explain what is wrong with the incorrect ones.
(a) $\mathrm{F}+\ddot{\mathrm{O}}: \mathrm{F}$
(b)
$\mathrm{OF}_{2}$
$: \mathrm{O} \equiv \mathrm{O}^{t}$
(c)
(d) $\mathrm{O}_{2}$ $\mathrm{H}: \ddot{\mathrm{C}} \cdot \mathrm{H} * \ddot{\mathrm{C}} 1$
$\mathrm{CH}_{3} \mathrm{Cl}$
<smiles>CO[N+](=O)[O-]</smiles> $\mathrm{CCl}_{2} \mathrm{O}$
(e)
$\mathrm{NO}_{2}^{-}$

Sandra Lundell
Sandra Lundell
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01:17

Problem 23

Write the structural formulas for all the branched-chain compounds with the molecular formula $\mathrm{C}_{4} \mathrm{H}_{10}$

Lottie Adams
Lottie Adams
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01:28

Problem 24

Write the structural formulas for all the branched-chain compounds with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14}$.

Lottie Adams
Lottie Adams
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01:37

Problem 25

Write structural formulas for two straight-chain alkenes with the formula $\mathrm{C}_{5} \mathrm{H}_{10}$. Are these the only two structures that meet these specifications?

Lottie Adams
Lottie Adams
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01:34

Problem 26

From their molecular formulas, classify each of these straight-chain hydrocarbons as an alkane, an alkene, or an alkyne.
(a) $\mathrm{C}_{5} \mathrm{H}_{8}$
(b) $\mathrm{C}_{24} \mathrm{H}_{50}$
(c) $\mathrm{C}_{7} \mathrm{H}_{1 i}$

Emily Himsel
Emily Himsel
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01:24

Problem 27

From their molecular formulas, classify each of these straight-chain hydrocarbons as an alkane, an alkene, or an alkyne.
(a) $\mathrm{C}_{21} \mathrm{H}_{44}$
(b) $\mathrm{C}_{4} \mathrm{H}_{6}$
(c) $\mathrm{C}_{\mathrm{g}} \mathrm{H}_{16}$

Emily Himsel
Emily Himsel
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00:59

Problem 28

Write the structural formulas for the cis and trans iso-
mers of 2 -pentene.

Emily Himsel
Emily Himsel
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03:19

Problem 29

The structural formulas are given for these cis or trans alkenes.
<smiles>CC(Cl)=C(Cl)C(C)Cl</smiles>
(a) $\mathrm{C}=\mathrm{C}-\mathrm{CH}_{3} \quad$ trans $-1,2$ -dichloropropene
(b) cis-2-pentene
(c) cis-3-hexene
(d) trans-2-hexene
Write the structural formula for
(a) cis-1,2-dichloropropene
(b) trans-2-pentene
(c) trans-3-hexene
(d) cis-2-hexene

Natalie Johns
Natalie Johns
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02:11

Problem 30

In each case, tell whether cis and trans isomers exist. If they do, write structural formulas for the two isomers and label each cis or trans.
(a) $\mathrm{Br}_{2} \mathrm{CH}_{2}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{5}$
(d) $\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}$

Natalie Johns
Natalie Johns
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06:24

Problem 31

Which of these molecules can have cis and trans isomers? For those that do, write the structural formulas of the two isomers and label each cis or trans. For those that cannot have these isomers, explain why.
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{BrC}=\mathrm{CBrCH}_{3}$
(b) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{lC}=\mathrm{ClCH}_{2} \mathrm{CH}_{3}$
(d) $\mathrm{CH}_{3} \mathrm{ClC}=\mathrm{CHCH}_{3}$
(e) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CHCH}_{3}$

Sandra Lundell
Sandra Lundell
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01:10

Problem 32

Oxalic acid has this structural formula.
<smiles>O=C(O)C(=O)O</smiles>
Is cis-trans isomerism possible for oxalic acid? Explain your answer.

Natalie Johns
Natalie Johns
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01:16

Problem 33

2 -methyl propene has this Lewis structure.
Is cis-trans isomerism possible for this molecule? Explain your answer.

Lottie Adams
Lottie Adams
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02:37

Problem 34

For each pair of bonds, predict which will be the shorter.
(a) $\mathrm{B}-\mathrm{Cl}$ or $\mathrm{Ga}-\mathrm{Cl}$
(b) $\mathrm{C}-\mathrm{O}$ or $\mathrm{Sn}-\mathrm{O}$
(c) $\mathrm{P}-\mathrm{S}$ or $\mathrm{P}-\mathrm{O}$
(d) The $\mathrm{C}=\mathrm{C}$ or the $\mathrm{C}=\mathrm{O}$ bond in acrolein

Lottie Adams
Lottie Adams
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02:15

Problem 35

For each pair of bonds, predict which will be the shorter.
(a) $\mathrm{Si}-\mathrm{N}$ or $\mathrm{P}-\mathrm{O}$
(b) $\mathrm{Si}-\mathrm{O}$ or $\mathrm{C}-\mathrm{O}$
(c) $\mathrm{C}-\mathrm{F}$ or $\mathrm{C}-\mathrm{Br}$
(d) The $\mathrm{C}=\mathrm{C}$ or the $\mathrm{C} \equiv \mathrm{N}$ bond in acrylonitrile, $\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}=\mathrm{N}$

Lottie Adams
Lottie Adams
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01:39

Problem 36

Using only a periodic table (not a table of bond energies), decide which of these is likely to be the strongest bond.
(a) $\mathrm{Si}=\mathbf{F}$
(b) $\mathrm{P}-\mathrm{S}$
(c) $\mathrm{P}=\mathrm{O}$

Lottie Adams
Lottie Adams
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00:56

Problem 37

Compare the nitrogen-nitrogen bonds in hydrazine, $\mathrm{N}_{2} \mathrm{H}_{4}$, and in "laughing gas," $\mathrm{N}_{2} \mathrm{O}$. In which molecule is the nitrogennitrogen bond shorter? In which should the nitrogen-nitrogen bond be stronger?

Natalie Johns
Natalie Johns
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01:11

Problem 38

Consider the carbon-oxygen bonds in formaldehyde, $\mathrm{H}_{2} \mathrm{CO}$, and in carbon monoxide, $\mathrm{CO}$. In which molecule is the carbon-oxygen bond shorter?

Lottie Adams
Lottie Adams
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00:52

Problem 39

Which bond will require more energy to break, the carbonoxygen bond in formaldehyde, $\mathrm{H}_{2} \mathrm{CO}$, or the $\mathrm{CO}$ bond in carbon monoxide, $\mathrm{CO}$ ?

Emily Himsel
Emily Himsel
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03:16

Problem 40

Compare the carbon-oxygen bond lengths in the formate ion, $\mathrm{HCO}_{2}^{-}$, and in the carbonate ion, $\mathrm{CO}_{3}^{2-} .$ In which ion is the bond longer? Explain briefly.

Lottie Adams
Lottie Adams
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01:54

Problem 42

Compare the nitrogen-oxygen bond lengths in $\mathrm{NO}_{2}^{+}$ and in $\mathrm{NO}_{3}^{-} .$ In which ion are the bonds longer? Explain briefly.

Lottie Adams
Lottie Adams
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02:58

Problem 42

Estimate $\Delta H^{\circ}$ for forming 2 mol ammonia from molecular nitrogen and molecular hydrogen. Is this reaction exothermic or endothermic? $\left(\mathrm{N}_{3}\right.$ has a triple bond.)

Sandra Lundell
Sandra Lundell
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01:35

Problem 43

Estimate $\Delta H^{\circ}$ for the conversion of $1 \mathrm{~mol}$ carbon monoxide to carbon dioxide by combination with molecular oxygen. Is this reaction exothermic or endothermic? (CO has a triple bond.)

Lottie Adams
Lottie Adams
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04:12

Problem 44

Which of the four molecules HF HCl, HBr, and HI has_the strongest chemical bond? Using bond energies, estimate $\Delta H^{\circ}$ for the reaction of molecular hydrogen with each of the gaseous molecular halogens: fluorine, chlorine, bromine, and iodine. Which is the most exothermic reaction?

Rabia Shuaib
Rabia Shuaib
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01:57

Problem 45

For each pair of bonds, indicate the more polar bond and use $\delta+$ or $\delta-$ to show the partial charge on each atom.
(a) $\mathrm{C}-\mathrm{O}$ and $\mathrm{C}-\mathrm{N}$
(b) $\mathrm{B}-\mathrm{O}$ and $\mathrm{P}-\mathrm{S}$
(c) $\mathbf{P}-\mathbf{H}$ and $\mathbf{P}-\mathbf{N}$
(d) $\mathbf{B}-\mathrm{H}$ and $\mathrm{B}-\mathrm{I}$

Emily Himsel
Emily Himsel
Numerade Educator
01:35

Problem 46

Given the bonds $\mathrm{C}-\mathrm{N}, \mathrm{C}-\mathrm{H}, \mathrm{C}-\mathrm{Br}$, and $\mathrm{S}-\mathrm{O}$
(a) Which atom in each is the more electronegative?
(b) Which of these bonds is the most polar?

Lottie Adams
Lottie Adams
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01:43

Problem 47

For each pair of bonds, identify the more polar one and use $\delta+$ or $\delta-$ to indicate the partial charge on each atom.
(a) $\mathrm{B}-\mathrm{Cl}$ and $\mathrm{B}-\mathrm{O}$
(b) $\mathrm{O}-\mathrm{F}$ and $\mathrm{O}-\mathrm{Se}$
(c) $\mathrm{S}-\mathrm{Cl}$ and $\mathrm{B}-\mathrm{F}$
(d) $\mathrm{N}-\mathrm{H}$ and $\mathrm{N}-\mathrm{F}$

Lottie Adams
Lottie Adams
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02:53

Problem 48

The molecule below is urea, a compound used in plastics and fertilizers.
urea
(a) Which bonds in the molecule are polar and which are nonpolar?
(b) Which is the most polar bond in the molecule? Which atom is the partial negative end of this bond?

Lottie Adams
Lottie Adams
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01:11

Problem 49

The molecule below is acrolein, the starting material for certain plastics.
acrolein
(a) Which bonds in the molecule are polar and which are nonpolar?
(b) Which is the most polar bond in the molecule? Which atom is the partial negative end of this bond?

Lottie Adams
Lottie Adams
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01:23

Problem 50

What is the total formal charge of a molecule? Of an ion?

Lottie Adams
Lottie Adams
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01:49

Problem 51

What is the relationship between formal charge and electronegativity?

Lottie Adams
Lottie Adams
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01:14

Problem 52

Write correct Lewis structures and assign a formal charge to each atom.
(a) $\mathrm{SO}_{3}$
(b) $\mathrm{C}_{2} \mathrm{~N}_{2}$ (atoms bonded in the order $\mathrm{NCCN}$ )
(c) $\mathrm{NO}_{2}^{-}$

Lottie Adams
Lottie Adams
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15:07

Problem 53

Write correct Lewis structures and assign a formal charge to each atom.
(a) $\mathrm{OCS}$
(b) HNC (atoms bonded in that order)
(c) $\mathrm{CH}_{3}^{-}$

Sandra Lundell
Sandra Lundell
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16:45

Problem 54

Write correct Lewis structures and assign a formal charge to each atom.
(a) $\mathrm{CH}_{4} \mathrm{CHO}$
(b) $\mathrm{N}_{3}^{-}$
(c) $\mathrm{CH}_{3} \mathrm{CN}$

Sandra Lundell
Sandra Lundell
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01:57

Problem 55

Write correct Lewis structures and assign a formal charge to
each atom.
(a) $\mathrm{KrF}_{4}$
(b) $\mathrm{ClO}_{3}^{-}$
(c) $\mathrm{SO}_{2} \mathrm{Cl}_{2}$

Lottie Adams
Lottie Adams
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03:09

Problem 56

Write the correct Lewis structure and assign a formal charge to each atom in fulminate ion, (CNO) $^{-}$.

Lottie Adams
Lottie Adams
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12:42

Problem 57

Peroxydisulfate ion, $\mathrm{S}_{2} \mathrm{O}_{8}^{2}$, is reduced to two sulfate ions, $\mathrm{SO}_{4}^{2-}$. Write the correct Lewis structures and assign a formal charge to each atom in the peroxydisulfate and sulfate ions.

Sandra Lundell
Sandra Lundell
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03:00

Problem 58

Two Lewis structures can be written for nitrosyl chloride, which contains one nitrogen, one oxygen, and one chlorine atom per molecule. Write the two Lewis structures and assign a formal charge to each atom.

Nicole Smina
Nicole Smina
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01:12

Problem 59

Two Lewis structures can be written for nitrosyl fluoride, which contains one nitrogen, one oxygen, and one fluorine atom per molecule. Write the two Lewis structures and assign a formal charge to each atom.

Lottie Adams
Lottie Adams
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01:59

Problem 60

These have two or more resonance structures. Write all the resonance structures for each.
(a) Nitric acid
<smiles>O=[N+]([O-])O</smiles>
(b) Nitrate ion, $\mathrm{NO}_{3}^{-}$

Natalie Johns
Natalie Johns
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13:24

Problem 61

These have two or more resonance structures. Write all the resonance structures for each molecule or ion.
(a) $\mathrm{SO}_{3}$
(b) $\mathrm{SCN}^{-}$

Sandra Lundell
Sandra Lundell
Numerade Educator
02:10

Problem 62

Several Lewis structures can be written for perbromate ion. $\mathrm{BrO}_{4}^{-}$, the central $\mathrm{Br}$ with all single $\mathrm{Br}-\mathrm{O}$ bonds, or with one, two, or three $\mathrm{Br}=\mathrm{O}$ double bonds. Draw the Lewis structures of these possible resonance forms, and use formal charges to predict the most plausible one.

Lottie Adams
Lottie Adams
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15:27

Problem 63

Use formal charges to predict which of the resonance forms is most plausible for
(a) $\mathrm{SO}_{3}$ and
(b) HNO $_{3}$ (See Question $60 .$ )

Sandra Lundell
Sandra Lundell
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02:11

Problem 64

Write the resonance structures for adenine, which is the nitrogen-containing organic base portion of the nucleic acid ATP (adenosine triphosphate).

Lottie Adams
Lottie Adams
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02:53

Problem 65

Several Lewis structures can be written for thiosulfate ion, $\mathrm{S}_{2} \mathrm{O}_{3}^{2-} .$ Write the Lewis structures of these possible resonance forms.

Rabia Shuaib
Rabia Shuaib
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08:11

Problem 66

Use formal charges to predict the most plausible Lewis structure for thiosulfate ion, $\mathrm{S}_{2} \mathrm{O}_{3}^{2-}$. (See Question 65.)

Sandra Lundell
Sandra Lundell
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06:10

Problem 67

Write the Lewis structure for each of these molecules or
ions.
(a) $\mathrm{BrF}_{5}$
(b) IF $_{5}$
(c) $\mathrm{IBr}_{2}$

Sandra Lundell
Sandra Lundell
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05:20

Problem 68

Write the Lewis structure for each of these molecules or
ions.
(a) $\mathrm{BrF}_{3}$
(b) $\mathrm{I}_{3}^{-}$
(c) XeF $_{4}$

Sandra Lundell
Sandra Lundell
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00:45

Problem 69

Which of these elements can form compounds with five or six pairs of valence electrons surrounding their atoms?
(a) $\mathrm{C}$
(b) $\mathbf{P}$
(c) $\overline{\mathrm{O}}$
(d) $\overline{\mathbf{F}}$
(e) $\overline{\mathrm{C}}$
(f) $\mathrm{B}$
(g) Se
(h) Sn

Emily Himsel
Emily Himsel
Numerade Educator
01:55

Problem 70

Carbon-to-carbon double bonds $(\mathrm{C}=\mathrm{C})$ react by addition. Cite experimental evidence that benzene does not have $\mathrm{C}=\mathrm{C}$ bonds.

Lottie Adams
Lottie Adams
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01:33

Problem 71

All carbon-to-carbon bond lengths are identical in benzene. Does this argue for or against the presence of $\mathrm{C}=\mathrm{C}$ bonds in benzene? Explain.

Lottie Adams
Lottie Adams
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01:41

Problem 72

Three dibromobenzenes are known. Write the Lewis structure and name for each compound.

Lottie Adams
Lottie Adams
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00:53

Problem 73

The structural formula of anthracene is
<smiles>c1ccc2cc3ccccc3cc2c1</smiles>
anthracene
What is its molecular formula?

Emily Himsel
Emily Himsel
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01:19

Problem 74

Write the structural formula for 1,2 -diiodobenzene (also
known as ortbo-diiodobenzene). Write the structural formulas for the meta and para isomers as well.

Lottie Adams
Lottie Adams
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01:56

Problem 75

Use MO theory to predict the MO diagram, the number of bonds, and the number of unpaired electrons in the nitrosyl ion, $\mathrm{NO}^{+}$.

CG
Chirag Gupta
Numerade Educator
01:56

Problem 76

Use MO theory to predict the number of electrons in each of the $2 s$ and $2 p$ molecular orbitals, the number of bonds, and the number of unpaired electrons in:
(a) CO
(b) $\overline{F_{2}}^{-}$
(c) $\mathrm{NO}^{-}$

Lottie Adams
Lottie Adams
Numerade Educator
01:25

Problem 77

Use MO theory to predict the number of bonds and the number of unpaired electrons in each of these ions:
(a) $\mathrm{B}_{2}^{+}$
(b) $\mathrm{Li}_{2}^{+}$
(c) $\mathrm{O}_{2}^{+}$

Lottie Adams
Lottie Adams
Numerade Educator
02:07

Problem 78

Using just a periodic table (not a table of electronegativities), decide which of these is likely to be the most polar bond. Explain your answer.
(a) $\mathrm{C}-\mathrm{F}$
(b) $\mathrm{S}-\mathrm{F}$
(c) $\mathrm{Si}=\mathbf{F}$
(d) $\mathrm{O}=\mathbf{F}$

Lijeesh Krishnan
Lijeesh Krishnan
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02:33

Problem 79

The $\mathrm{C}-\mathrm{Br}$ bond length in $\mathrm{CBr}_{4}$ is $191 \mathrm{pm} ;$ the $\mathrm{Br}-\mathrm{Br}$ distance in $\mathrm{Br}_{2}$ is $228 \mathrm{pm}$. Estimate the radius of a $\mathrm{C}$ atom in $\mathrm{CBr}_{4}$. Use this value to estimate the $\mathrm{C}-\mathrm{C}$ distance in ethane, $\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{3} .$ How does your calculated bond length agree with the measured value of $154 \mathrm{pm}$ ? Are radii of atoms exactly the same in every molecule?

Lottie Adams
Lottie Adams
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01:20

Problem 80

Is it a good generalization that elements that are close together in the periodic table form covalent bonds, whereas elements that are far apart form ionic bonds? Why or why not?

Lottie Adams
Lottie Adams
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01:14

Problem 81

Write Lewis structures for:
(a) $\mathrm{CS}_{2}$
(b) $\mathrm{NH}_{2} \mathrm{OH}$
(c) $\mathrm{S}_{2} \mathrm{Cl}_{2}$ (contains $\mathrm{S}-\mathrm{S}$ bond $)$
(d) $\mathrm{NS}_{2}^{+}$

Lottie Adams
Lottie Adams
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01:30

Problem 82

The molecule pictured below is acrylonitrile, the building block of the synthetic fiber Orlon.
(a) Which is the shorter carbon-carbon bond?
(b) Which is the stronger carbon-carbon bond?
(c) Which is the most polar bond and what is the partial negative end of the bond?

Lottie Adams
Lottie Adams
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01:31

Problem 83

In nitryl chloride, $\mathrm{NO}_{2} \mathrm{Cl}$, there is no oxygen-oxygen bond. Write a Lewis structure for the molecule. Write any resonance structures for this molecule.

Lottie Adams
Lottie Adams
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01:41

Problem 84

Write Lewis structures for:
(a) $\mathrm{SCl}_{2}$
(b) $\mathrm{Cl}_{3}^{+}$
(c) $\mathrm{ClOClO}_{3}$ (contains $\mathrm{Cl}-\mathrm{O}-\mathrm{Cl}$ bond $)$
(d) $\mathrm{SOCl}_{2}$

Emily Himsel
Emily Himsel
Numerade Educator
01:12

Problem 85

Arrange these bonds in order of increasing length (shortest first). List all the factors responsible for each placement:
$\mathrm{O}-\mathrm{H}, \mathrm{O}-\mathrm{O}, \mathrm{Cl}-\mathrm{O}, \mathrm{O}=\mathrm{O}, \mathrm{O}=\mathrm{C}$

Lottie Adams
Lottie Adams
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01:16

Problem 86

List the bonds in Question 85 in order of increasing bond strengtb.

Lottie Adams
Lottie Adams
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01:19

Problem 87

Chlorine trifluoride, $\mathrm{CIF}_{3}$, is one of the most reactive compounds known. Write the Lewis structure for $\mathrm{CIF}_{3}$

Lottie Adams
Lottie Adams
Numerade Educator
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Problem 88

Judging from the number of carbon and hydrogen atoms in their formulas, which of these formulas represent alkanes? Which are likely aromatic? Which fall into neither category? (It may help to write structural formulas.)
(a) $\mathrm{C}_{8} \mathrm{H}_{10}$
(b) $\mathrm{C}_{10} \mathrm{H}_{\mathrm{g}}$
(c) $\mathrm{C}_{6} \mathrm{H}_{12}$
(d) $\mathrm{C}_{6} \mathrm{H}_{14}$
(e) $\mathrm{C}_{\mathrm{g}} \mathrm{H}_{18}$
(f) $\mathrm{C}_{6} \mathrm{H}_{10}$

Emily Himsel
Emily Himsel
Numerade Educator
01:32

Problem 89

A student drew this incorrect Lewis structure for $\mathrm{ClO}_{3}^{-}$. What errors were made when determining the number of valence electrons?

Lottie Adams
Lottie Adams
Numerade Educator
01:26

Problem 90

This Lewis structure for $\mathrm{SF}_{5}^{+}$ is drawn incorrectly. What error was made when determining the number of valence electrons?

Lottie Adams
Lottie Adams
Numerade Educator
00:55

Problem 91

Tribromide, $\mathrm{Br}_{3}^{-}$, and triiodide, $\mathrm{I}_{3}^{-}$, ions exist, but trifluoride ion, $\mathrm{F}_{x}^{-}$, is not known. Explain.

Emily Himsel
Emily Himsel
Numerade Educator
01:09

Problem 92

Explain why nonmetal atoms in Period 3 and beyond can accommodate greater than an octet of electrons and those in Period 2 cannot do so.

Lottie Adams
Lottie Adams
Numerade Educator
00:52

Problem 93

When asked to give an example of resonance structures, a student drew these Lewis structures. Why is this example incorrect?

Emily Himsel
Emily Himsel
Numerade Educator
01:18

Problem 94

Why is this not an example of resonance structures?

Lottie Adams
Lottie Adams
Numerade Educator
01:31

Problem 95

How many bonds would you expect the elements in Groups 3 A through $7 \mathrm{~A}$ to form if they obeyed the octet rule?

Lottie Adams
Lottie Adams
Numerade Educator
01:21

Problem 96

In another universe, elements try to achieve a nonet (nine valence electrons) instead of an octet when forming chemical bonds. As a result, covalent bonds form when a trio of electrons are shared between two atoms. Draw Lewis structures for the compounds that would form between (a) hydrogen and oxygen and (b) hydrogen and fluorine.

Lottie Adams
Lottie Adams
Numerade Educator
01:23

Problem 97

Elemental phosphorus has the formula $\mathrm{P}_{4} .$ Propose a Lewis structure for this molecule. [Hints: (1) Each phosphorus atom is bonded to three other phosphorus atoms. (2) Visualize the structure three-dimensionally, not flat on a page.]

Lottie Adams
Lottie Adams
Numerade Educator
02:46

Problem 98

The elements As, Br, Cl, S, and Se have electronegativity values of $2.1,2.4,2.5$, and $3.0$, but not in that order. Using the periodic trend for electronegativity, assign the values to the elements. Which assignments are you certain about? Which are you not?

Natalie Johns
Natalie Johns
Numerade Educator
11:30

Problem 99

A substance is analyzed and found to contain $85.7 \%$ carbon and $14.3 \%$ hydrogen by weight. A gaseous sample of the substance is found to have a density of $1.87 \mathrm{~g} / \mathrm{L}$, and $1 \mathrm{~mol}$ of it occupies a volume of $22.4 \mathrm{~L}$. What are two possible Lewis structures for molecules of the compound? (Hint:
First determine the empirical formula and molar mass of the substance.)

Sandra Lundell
Sandra Lundell
Numerade Educator
00:43

Problem 100

Which of these molecules is least likely to exist: $\mathrm{NF}_{5}, \mathrm{PF}_{5}$, $\mathrm{SbF}_{5}$, or IF ? Explain why.

Emily Himsel
Emily Himsel
Numerade Educator
03:10

Problem 101

When we estimate $\Delta H^{\circ}$ from bond enthalpies we assume that all bonds of the same type (single, double, triple) between the same two atoms have the same energy, regardless of the molecule in which they occur. The purpose of this problem is to show you that this is only an approximation. You will need the following standard enthalpies of formation:
$$
\begin{array}{ll}
\mathrm{C}(\mathrm{g}) & \Delta H^{\circ}=716.7 \mathrm{~kJ} / \mathrm{mol} \\
\mathrm{CH}(\mathrm{g}) & \Delta H^{\circ}=596.3 \mathrm{~kJ} / \mathrm{mol} \\
\mathrm{CH}_{2}(\mathrm{~g}) & \Delta H^{\circ}=392.5 \mathrm{~kJ} / \mathrm{mol} \\
\mathrm{CH}_{3}(\mathrm{~g}) & \Delta H^{\circ}=146.0 \mathrm{~kJ} / \mathrm{mol} \\
\mathrm{H}(\mathrm{g}) & \Delta H^{\circ}=218.0 \mathrm{~kJ} / \mathrm{mol}
\end{array}
$$
(a) What is the average $\mathrm{C}-\mathrm{H}$ bond energy in methane, $\mathrm{CH}_{4} ?$
(b) Using bond enthalpies, estimate $\Delta H^{\circ}$ for the reaction
$$
\mathrm{CH}_{4}(\mathrm{~g}) \longrightarrow \mathrm{C}(\mathrm{g})+2 \mathrm{H}_{2}(\mathrm{~g})
$$
(c) By heating $\mathrm{CH}_{4}$ in a flame it is possible to produce the reactive gaseous species $\mathrm{CH}_{3}, \mathrm{CH}_{2}, \mathrm{CH}$, and even carbon atoms, $\mathrm{C}$. Experiments give these values of $\Delta H^{\circ}$ for the reactions shown:
$$
\begin{array}{ll}
\mathrm{CH}_{3}(\mathrm{~g}) \longrightarrow \mathrm{C}(\mathrm{g})+\mathrm{H}_{2}(\mathrm{~g})+\mathrm{H}(\mathrm{g}) & \Delta H^{\circ}=788.7 \mathrm{~kJ} \\
\mathrm{CH}_{2}(\mathrm{~g}) \longrightarrow \mathrm{C}(\mathrm{g})+\mathrm{H}_{2}(\mathrm{~g}) & \Delta H^{\circ}=324.2 \mathrm{~kJ}
\end{array}
$$
$\mathrm{CH}(\mathrm{g}) \longrightarrow \mathrm{C}(\mathrm{g})+\mathrm{H}(\mathrm{g})$
$\Delta H^{\circ}=338.3 \mathrm{~kJ}$
For each of these reactions, draw a diagram similar to Figure $8.4$. Then calculate the average $\mathrm{C}-\mathrm{H}$ bond energy in $\mathrm{CH}_{5}, \mathrm{CH}_{2}$, and $\mathrm{CH}$. Comment on any trends you see.

Rabia Shuaib
Rabia Shuaib
Numerade Educator
08:18

Problem 102

Write the Lewis structure for nitrosyl fluoride, FNO. Using only a periodic table, identify:
(a) Which is the longest bond.
(b) Which is the strongest bond.
(c) Which is the most polar bond.

Sandra Lundell
Sandra Lundell
Numerade Educator
08:50

Problem 103

Write the Lewis structure for nitrosyl chloride, CINO. Using only a periodic table, identify:
(a) Which is the longest bond.
(b) Which is the strongest bond.
(c) Which is the most polar bond.

Sandra Lundell
Sandra Lundell
Numerade Educator
01:35

Problem 104

Methylcyanoacrylate is the active ingredient in "super" glues. Its Lewis structure is
In this molecule, which is the:
(a) Weakest carbon-containing bond?
(b) Strongest carbon-containing bond?
(c) Most polar bond?

Lottie Adams
Lottie Adams
Numerade Educator
01:14

Problem 105

Acrylonitrile is used to made synthetic carpets and wigs. Its Lewis structure is
In this molecule, which is the:
(a) Strongest carbon-containing bond?
(b) Second strongest carbon-containing bond?
(c) Most polar bond?

Natalie Johns
Natalie Johns
Numerade Educator
02:44

Problem 106

Write the Lewis structure for:
(a) tetraboron tetrachloride, $\mathrm{B}_{4} \mathrm{Cl}_{4}$
(b) hyponitrous acid, $\mathrm{H}_{2} \mathrm{~N}_{2} \mathrm{O}_{2}$

Rabia Shuaib
Rabia Shuaib
Numerade Educator
01:29

Problem 107

Nitrosyl azide, $\mathrm{N}_{4} \mathrm{O}$, is a pale yellow solid first synthesized in $1993 .$ Write the Lewis structure for nitrosyl azide.

Lottie Adams
Lottie Adams
Numerade Educator
02:38

Problem 108

Write the Lewis structures for
(a) $\left(\mathrm{Cl}_{2} \mathrm{PN}\right)_{3}$
(b) $\left(\mathrm{Cl}_{2} \overline{\mathrm{PN}}\right)_{4}$

Lottie Adams
Lottie Adams
Numerade Educator
01:00

Problem 109

Write the Lewis structures for:
(a) dithiocyanogen, (NCS),
(b) tetrahydrofuran, $\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}$

Lottie Adams
Lottie Adams
Numerade Educator
00:46

Problem 110

In sulfuric acid production, sulfur trioxide is combined with sulfuric acid to produce oleum, which contains $\mathrm{H}_{2} \mathrm{~S}_{2} \mathrm{O}_{7}$ Write the Lewis structure for this compound.

Emily Himsel
Emily Himsel
Numerade Educator
07:36

Problem 111

Tetrasulfur tetranitride, $\mathrm{S}_{4} \mathrm{~N}_{4}$, can be converted to disulfur dinitride, $\mathrm{S}_{2} \mathrm{~N}_{2} .$ Write the Lewis structures for these compounds.

Sandra Lundell
Sandra Lundell
Numerade Educator
01:45

Problem 112

Write the Lewis structures for:
(a) hyponitrite ion, $\left(\mathrm{N}_{2} \mathrm{O}_{2}\right)^{2-}$
(b) $\left(\mathrm{SO}_{3}\right)_{3}$

Nicholas Mogoi
Nicholas Mogoi
Numerade Educator
12:36

Problem 113

Write the Lewis structures for.
(a) $\mathrm{S}_{2} \mathrm{~F}_{10}$
(b) $\mathrm{FXeN}\left(\mathrm{SO}_{2} \mathrm{~F}\right)_{2}$

Sandra Lundell
Sandra Lundell
Numerade Educator
01:08

Problem 114

Experimental evidence indicates the existence of $\mathrm{HC}_{3} \mathrm{~N}$ molecules in interstellar clouds. Write a plausible Lewis structure for this molecule.

Lottie Adams
Lottie Adams
Numerade Educator
01:42

Problem 115

Molecules of $\mathrm{SiC}_{3}$ have been discovered in interstellar clouds. Write a plausible Lewis structure for this molecule.

Lottie Adams
Lottie Adams
Numerade Educator
11:48

Problem 116

For many people, tears flow when they cut raw onions. The tear-inducing agent is thiopropionaldehyde-S-oxide, $\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{OS}$. Write the Lewis structure for this compound.

Sandra Lundell
Sandra Lundell
Numerade Educator
05:10

Problem 117

One of the structural isomers of $\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{OS}$ is the compound that is the offending odorant released by striped skunks. Write Lewis structures for two isomers of this compound.

Sandra Lundell
Sandra Lundell
Numerade Educator
02:07

Problem 118

Phosphorus and sulfur form a series of compounds, one of which is tetraphosphorus trisulfide. Write the Lewis structure for this compound.

Natalie Johns
Natalie Johns
Numerade Educator
02:02

Problem 119

Piperine, the active ingredient in black pepper, has the structural formula given below.
(a) Write the molecular formula of piperine.
(b) Identify the shortest carbon-to-carbon bond in piperine.
(c) Identify the shortest carbon-to-oxygen bond in piperine.
(d) Identify the stongest carbon-to-carbon bond in piperine.
(e) Identify the most polar bond in piperine.

Natalie Johns
Natalie Johns
Numerade Educator
01:27

Problem 120

Gamma-aminobutanoic acid, $\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{O}_{2} \mathrm{~N}$, is a neurotransmitter. The molecule contains a four-carbon chain.
(a) Write the Lewis structure for this molecule.
(b) Which bond is the longest?
(c) Which bond is the most polar?
(d) Which bond is the strongest?

Lottie Adams
Lottie Adams
Numerade Educator
01:17

Problem 121

Suppose in building up molecular orbitals, the $\pi_{2 p}$ were placed above the $\sigma_{2 p}$. Prepare a diagram similar to Figure $8.11$ based on these changes. For which species in Table $8.4$ would this change in relative energies of the MOs affect the prediction of number of bonds and number of unpaired electrons?

Lottie Adams
Lottie Adams
Numerade Educator