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Chemistry Structure and Properties

Nivaldo J. Tro

Chapter 6

Chemical Bonding I: drawing Lewis Structures and determining Molecular Shapes - all with Video Answers

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Chapter Questions

02:55

Problem 1

What is electronegativity? What are the periodic trends in electronegativity?

Nadia Lara
Nadia Lara
Numerade Educator
02:00

Problem 2

Explain the difference between a pure covalent bond, a polar covalent bond, and an ionic bond.

Wilson Ma
Wilson Ma
The University of Alabama
01:51

Problem 3

What is meant by the percent ionic character of a bond? Do any bonds have 100$\%$ ionic character?

Keenan Mintz
Keenan Mintz
University of Miami
02:22

Problem 4

What is a dipole moment?

Mercedes Mazza
Mercedes Mazza
Numerade Educator
03:26

Problem 5

What is the magnitude of the dipole moment formed by separating a proton and an electron by 100 pm? 200 pm?

Nadia Lara
Nadia Lara
Numerade Educator
02:24

Problem 6

What is the basic procedure for writing a covalent Lewis structure?

Mercedes Mazza
Mercedes Mazza
Numerade Educator
02:06

Problem 7

How do you determine the number of electrons that go into the Lewis structure of a molecule? A polyatomic ion?What are resonance structures? What is a resonance hybrid?

Madi Sousa
Madi Sousa
Numerade Educator
02:18

Problem 8

What are resonance structures? What is a resonance hybrid?

Mercedes Mazza
Mercedes Mazza
Numerade Educator
02:23

Problem 9

Do resonance structures always contribute equally to the overall
structure of a molecule? Explain.

Nadia Lara
Nadia Lara
Numerade Educator
04:41

Problem 10

What is formal charge? How is formal charge calculated? How is it
helpful?

Mercedes Mazza
Mercedes Mazza
Numerade Educator
02:24

Problem 11

Why does the octet rule have exceptions? Give the three major
categories of exceptions and an example of each.

Keenan Mintz
Keenan Mintz
University of Miami
02:24

Problem 12

Why does the octet rule have exceptions? Give the three major categories of exceptions and an example of each.

Keenan Mintz
Keenan Mintz
University of Miami
01:22

Problem 13

What is bond energy?

Keenan Mintz
Keenan Mintz
University of Miami
01:03

Problem 14

Give some examples of some typical bond lengths. Which factors in-
fluence bond lengths?

Madi Sousa
Madi Sousa
Numerade Educator
00:59

Problem 15

Why is molecular geometry important? Cite some examples.

Rashmi Sinha
Rashmi Sinha
Numerade Educator
01:09

Problem 16

According to VSEPR theory, what determines the geometry of a molecule?

ES
Eugene Schneider
University of Minnesota - Twin Cities
06:17

Problem 17

Name and draw the five basic electron geometries, and state the number of
electron groups corresponding to each. What constitutes an electron group?

Keenan Mintz
Keenan Mintz
University of Miami
01:24

Problem 18

Explain the difference between electron geometry and molecular geometry. Under what circumstances are they not the same?

ES
Eugene Schneider
University of Minnesota - Twin Cities
02:14

Problem 19

List the correct electron and molecular geometries that correspond to
each set of electron groups around the central atom of a molecule.
\begin{equation}\begin{array}{l}{\text { a. four electron groups overall; three bonding groups and one lone pair }} \\ {\text { b. four electron groups overall; two bonding groups and two lone pair }} \\ {\text { c. five electron groups overall; four bonding groups and one lone pair }} \\ {\text { d. five electron groups overall; three bonding groups and two lone pairs }}\end{array}\end{equation}\begin{equation}\begin{array}{l}{\text { e. five electron groups overall; two bonding groups and three lone pairs }} \\ {\text { f. sixe electron groups overall; five bonding groups and one lone pair }} \\ {\text { g. six electron groups overall; four bonding groups and two lone pairs }}\end{array}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
View

Problem 20

How do you apply VSEPR theory to predict the shape of a molecule
with more than one interior atom?

Emily Himsel
Emily Himsel
Numerade Educator
02:17

Problem 21

How do you determine if a molecule is polar?

Keenan Mintz
Keenan Mintz
University of Miami
01:09

Problem 22

Why is polarity a key connection between the structure of a molecule
and its properties?

Wilson Ma
Wilson Ma
The University of Alabama
01:59

Problem 23

Determine if a bond between each pair of atoms would be pure covalent, polar covalent, or ionic.
a. $\mathrm{Br}$ and $\mathrm{Br}$
b. $\mathrm{C}$ and $\mathrm{Cl}$
c. $\mathrm{C}$ and $\mathrm{S} \quad$
d. $\quad$ Sr and $\mathrm{O}$

Nadia Lara
Nadia Lara
Numerade Educator
02:36

Problem 24

Determine if a bond between each pair of atoms would be pure covalent, polar covalent, or ionic.
a. $\mathrm{C}$ and $\mathrm{N} \quad$ b. $\mathrm{N}$ and $\mathrm{S}$ c. $\mathrm{K}$ and $\mathrm{F} \quad$ d. $\quad \mathrm{N}$ and $\mathrm{N}$

Mercedes Mazza
Mercedes Mazza
Numerade Educator
02:48

Problem 25

Draw the Lewis structure for CO with an arrow representing the
dipole moment. Use Figure 6.5 to estimate the percent ionic character
of the CO bond.

Dr.  Satish  Ingale
Dr. Satish Ingale
Numerade Educator
01:08

Problem 26

Draw the Lewis structure for BrF with an arrow representing the dipole moment. Use Figure 6.5 to estimate the percent ionic character of the BrF bond.

Wilson Ma
Wilson Ma
The University of Alabama
05:35

Problem 27

Write the Lewis structure for each molecule.
a. PH $_{3} \quad$ b. $\mathrm{SCl}_{2} \quad$ c. HI $\quad$ d. $\mathrm{CH}_{4}$

Marjeta Wolfe
Marjeta Wolfe
Numerade Educator
07:10

Problem 28

Write the Lewis structure for each molecule.
a. $\mathrm{NF}_{3} \quad$ b. HBr $\quad$ c. $\mathrm{SBr}_{2} \quad$ d. $\mathrm{CCl}_{4}$

Bryan Li
Bryan Li
Numerade Educator
07:15

Problem 29

Write the Lewis structure for each molecule.
$\begin{array}{ll}{\text { a. } S F_{2}} & {\text { b. } \operatorname{SiH}_{4}} \\ {\text { c. HCOOH (both O bonded to } C )} & {\text { d. } C H_{3} S H(C \text { and } S \text { central) }}\end{array}$

Nadia Lara
Nadia Lara
Numerade Educator
07:42

Problem 30

Write the Lewis structure for each molecule.
a. $\mathrm{CH}_{2} \mathrm{O} \quad$ b. $\mathrm{C}_{2} \mathrm{Cl}_{4}$

Bryan Li
Bryan Li
Numerade Educator
10:55

Problem 31

Write the Lewis structure for each molecule or ion.
a. $\mathrm{CI}_{4} \quad$ b. $\mathrm{N}_{2} \mathrm{O}$ $\mathrm{c} . \mathrm{SiH}_{4} \quad$ d. $\mathrm{Cl}_{2} \mathrm{CO}$

Bryan Li
Bryan Li
Numerade Educator
04:28

Problem 32

Write the Lewis structure for each molecule or ion.
a. $\mathrm{H}_{3} \mathrm{COH} \quad$ b. $\mathrm{OH}^{-}$ c. $\mathrm{BrO}^{-} \quad$ d. $\mathrm{O}_{2}^{2-}$

Mercedes Mazza
Mercedes Mazza
Numerade Educator
09:37

Problem 33

Write the Lewis structure for each molecule or ion.
\begin{equation}\mathrm a.{N}_{2} \mathrm{H}_{2} \quad \text { b. } \mathrm{N}_{2} \mathrm{H}_{4}
\end{equation}\begin{equation} \mathrm c.{C}_{2} \mathrm{H}_{2} \quad \text { d. } \mathrm{C}_{2} \mathrm{H}_{4}\end{equation}

Nadia Lara
Nadia Lara
Numerade Educator
03:58

Problem 34

Write the Lewis structure for each molecule or ion.
\begin{equation}\mathrm a.{H}_{3} \mathrm{COCH}_{3} \text { b. } \mathrm{CN}^{-}\end{equation}\begin{equation}
\mathrm c.{NO}_{2}^{-} \quad \text { d. } \mathrm{ClO}^{-}\end{equation}

Mercedes Mazza
Mercedes Mazza
Numerade Educator
08:06

Problem 35

Write a Lewis structure that obeys the octet rule for each molecule or
ion. Include resonance structures if necessary and assign formal charges
to each atom.
\begin{equation}
\mathrm { a. } {SeO}_{2} \quad \text { b. } \mathrm{CO}_{3}^{2-} \quad \text { c. } \mathrm{ClO}^{-} \quad \text { d. } \mathrm{NO}_{2}^{-}
\end{equation}

Alexandra Grace
Alexandra Grace
Numerade Educator
02:57

Problem 36

Write a Lewis structure that obeys the octet rule for each ion. Include
resonance structures if necessary and assign formal charges to each atom.
\begin{equation}\mathrm { a. }{ClO}_{3}^{-} \quad \text { b. } \mathrm{ClO}_{4}^{-} \quad \text { c. } \mathrm{NO}_{3}^{-} \quad \text { d. } \mathrm{NH}_{4}^{+}\end{equation}

Tiffany Noble
Tiffany Noble
Numerade Educator
View

Problem 37

Use formal charge to determine which Lewis structure is better.

Andrew Eddins
Andrew Eddins
Emory University
View

Problem 38

Use formal charge to determine which Lewis structure is better.

Andrew Eddins
Andrew Eddins
Emory University
02:52

Problem 39

How important is this resonance structure to the overall structure of car-
bon dioxide? Explain.

Bryan Li
Bryan Li
Numerade Educator
01:48

Problem 40

In $\mathrm{N}_{2} \mathrm{O},$ nitrogen is the central atom and the oxygen atom is terminal.
In $\mathrm{OF}_{2},$ however, oxygen is the central atom. Use formal charges to
explain why.

Tiffany Noble
Tiffany Noble
Numerade Educator
04:14

Problem 41

Draw the Lewis structure (including resonance structures) for the acetate
ion $\left(\mathrm{CH}_{3} \mathrm{COO}^{-}\right) .$ For each resonance structure, assign formal charges to all atoms that have formal charge.

Nadia Lara
Nadia Lara
Numerade Educator
02:24

Problem 42

Draw the Lewis structure (including resonance structures) for methyl
azide $\left(\mathrm{CH}_{3} \mathrm{N}_{3}\right) .$ For each resonance structure, assign formal charges to all atoms that have formal charge.

Tiffany Noble
Tiffany Noble
Numerade Educator
01:08

Problem 43

What are the formal charges of the atoms shown in red?

Nicole Krahulik
Nicole Krahulik
Numerade Educator
01:08

Problem 44

What are the formal charges of the atoms shown in red?

Nicole Krahulik
Nicole Krahulik
Numerade Educator
03:08

Problem 45

Write the Lewis structure for each molecule (octet rule not followed).
\begin{equation}\mathrm{ a.} {BCl}_{3} \quad \text { b. } \mathrm{NO}_{2} \quad \text { c. } \mathrm{BH}_{3}\end{equation}

Nadia Lara
Nadia Lara
Numerade Educator
01:39

Problem 46

Write the Lewis structure for each molecule (octet rule not followed).
\begin{equation}\mathrm { a. } {BBr}_{3} \quad \text { b. NO } \quad \text { c. } \mathrm{ClO}_{2}\end{equation}

Mercedes Mazza
Mercedes Mazza
Numerade Educator
08:10

Problem 47

Write the Lewis structure for each ion. Include resonance structures if
necessary and assign formal charges to all atoms. If necessary, expand
the octet on the central atom to lower formal charge.
\begin{equation}\mathrm{ a.} {PO}_{4}^{3-} \quad \text { b. } \mathrm{CN}^{-} \quad \text { c. } \mathrm{SO}_{3}^{2-} \quad \text { d. } \mathrm{ClO}_{2}^{-}\end{equation}

Lewis Rose
Lewis Rose
Numerade Educator
12:09

Problem 48

Write Lewis structures for each molecule or ion. Include resonance
structures if necessary and assign formal charges to all atoms. If you
need to, expand the octet on the central atom to lower formal charge.
\begin{equation}\mathrm{ a.} {SO}_{4}^{2-} \quad \text { b. } \mathrm{HSO}_{4}^{-} \quad \text { c. } \mathrm{SO}_{3} \quad \text { d. } \mathrm{BrO}_{2}^{-}\end{equation}

Bryan Li
Bryan Li
Numerade Educator
09:51

Problem 49

Write Lewis structures for each molecule or ion. Use expanded octets as necessary.
\begin{equation}\begin{array}{lllll}{\text { a. } \mathrm{PF}_{5}} & {\text { b. } \mathrm{I}_{3}^{-}} & {\text { c. }} & {\mathrm{SF}_{4}} & {\text { d. GeF }_{4}}\end{array}\end{equation}

Bryan Li
Bryan Li
Numerade Educator
11:04

Problem 50

Write Lewis structures for each molecule or ion. Use expanded octets
as necessary.
\begin{equation}\mathrm{ a. }{ClF}_{5} \quad \text { b. } \mathrm{AsF}_{6}-\quad \text { c. } \mathrm{Cl}_{3} \mathrm{PO} \quad \text { d. IF }_{5}\end{equation}

Bryan Li
Bryan Li
Numerade Educator
02:12

Problem 51

Order these compounds in order of increasing carbon-carbon bond
strengtb and in order of decreasing carbon-carbon bond length:
HCCH, $\mathrm{H}_{2} \mathrm{CCH}_{2}, \mathrm{H}_{3} \mathrm{CCH}_{3}$

Bryan Li
Bryan Li
Numerade Educator
02:10

Problem 52

Which of these compounds has the stronger nitrogen-nitrogen bond?
The shorter nitrogen-nitrogen bond?
$\mathrm{H}_{2} \mathrm{NNH}_{2}, \mathrm{HNNH}$

Bryan Li
Bryan Li
Numerade Educator
02:06

Problem 53

A molecule with the formula AB3 has a trigonal pyramidal geometry.
How many electron groups are on the central atom (A)?

Arun Bana
Arun Bana
Numerade Educator
03:24

Problem 54

A molecule with the formula AB3 has a trigonal planar geometry.
How many electron groups are on the central atom?

Shazia Naz
Shazia Naz
Numerade Educator
03:22

Problem 55

For each molecular geometry shown here, list the number of total elec-
tron groups, the number of bonding groups, and the number of lone

pairs on the central atom.

Bryan Li
Bryan Li
Numerade Educator
02:38

Problem 56

For each molecular geometry shown here, list the number of total electron groups, the number of bonding groups, and the number of lone pairs on the central atom.

KC
Kara Cecil
Numerade Educator
01:35

Problem 57

Determine the electron geometry, molecular geometry, and idealized
bond angles for each molecule. In which cases do you expect deviations
from the idealized bond angle?
\begin{equation}\mathrm{ a. } {PF}_{3} \quad \text { b. } \mathrm{SBr}_{2}\end{equation} \begin{equation}\mathrm{ c. }{CHCl}_{3} \quad \text { d. } \mathrm{CS}_{2}\end{equation}

Lottie Adams
Lottie Adams
Numerade Educator
03:03

Problem 58

Determine the electron geometry, molecular geometry, and idealized
bond angles for each molecule. In which cases do you expect deviations
from the idealized bond angle?
\begin{equation}\begin{array}{lllll}{\text { a. } \mathrm{CF}_{4}} & {\text { b. } \mathrm{NF}_{3}} & {\text { c. } \mathrm{OF}_{2}} & {\text { d. } \mathrm{H}_{2} \mathrm{S}}\end{array}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
00:39

Problem 59

Which species has the smaller bond angle, $\mathrm{H}_{3} \mathrm{O}^{+}$ or $\mathrm{H}_{2} \mathrm{O}$ ? Explain.

Lottie Adams
Lottie Adams
Numerade Educator
05:03

Problem 60

Which species has the smaller bond angle, $\mathrm{ClO}_{4}^{-}$ or $\mathrm{ClO}_{3}^{-}$ or ? Explain.

Bryan Li
Bryan Li
Numerade Educator
13:47

Problem 61

Determine the molecular geometry and draw each molecule or ion using
the bond conventions shown in the "Representing Molecular Geometries
on Paper"'section of this chapter (see Section 6.9$) .$
\begin{equation}\mathrm{ a. } {SF}_{4} \quad \text { b. } \mathrm{CIF}_{3} \quad \text { c. IF }_{2}^{-} \quad \text { d. IBr }_{4}^{-}\end{equation}

Aparna Shakti
Aparna Shakti
Numerade Educator
02:47

Problem 62

Determine the molecular geometry and draw each molecule or ion, using
the bond conventions shown in the "Representing Molecular Geometries
on Paper" section of this chapter (see Section 6.9$) .$
a. $\mathrm{BrF}_{5} \quad$ b. $\mathrm{SCl}_{6}$ c. $\mathrm{PF}_{5} \quad$ d. IF $_{4}^{+}$

Madi Sousa
Madi Sousa
Numerade Educator
01:37

Problem 63

Determine the molecular geometry about each interior atom and draw
each molecule. (Skeletal structure is indicated in parentheses.)
\begin{equation}\begin{array}{l}{\text { a. } C_{2} \mathrm{H}_{2}(\mathrm{HCCH})} \\ {\text { b. } \mathrm{C}_{2} \mathrm{H}_{4}\left(\mathrm{H}_{2} \mathrm{CCH}_{2}\right)} \\ {\text { c. } \mathrm{C}_{2} \mathrm{H}_{6}\left(\mathrm{H}_{3} \mathrm{CCH}_{3}\right)}\end{array}
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
01:30

Problem 64

Determine the molecular geometry about each interior atom and draw
each molecule. (Skeletal structure is indicated in parentheses.)
\begin{equation}\begin{array}{l}{\text { a. } \mathrm{N}_{2}} \\ {\text { b. } \mathrm{N}_{2} \mathrm{H}_{2}(\mathrm{HNNH})} \\ {\text { c. } \mathrm{N}_{2} \mathrm{H}_{4}\left(\mathrm{H}_{2} \mathrm{NN} \mathrm{H}_{2}\right)}\end{array}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
03:32

Problem 65

Each ball-and-stick model shows the electron and molecular geometry of
a generic molecule. Explain what is wrong with each molecular geometry
and provide the correct molecular geometry, given the number of lone
pairs and bonding groups on the central atom.

Keenan Mintz
Keenan Mintz
University of Miami
03:32

Problem 66

Each ball-and-stick model shows the electron and molecular geometry of
a generic molecule. Explain what is wrong with each molecular geometry
and provide the correct molecular geometry, given the number of lone
pairs and bonding groups on the central atom.

Keenan Mintz
Keenan Mintz
University of Miami
02:10

Problem 67

Determine the geometry about each interior atom in each molecule
and draw the molecule. (Skeletal structure is indicated in parentheses.)
\begin{equation}\mathrm{a} . \mathrm{CH}_{3} \mathrm{OH}\left(\mathrm{H}_{3} \mathrm{COH}\right)
\end{equation} \begin{equation}\mathrm{ b. } {CH}_{3} \mathrm{OCH}_{3}\left(\mathrm{H}_{3} \mathrm{COCH}_{3}\right)
\end{equation} \begin{equation}\mathrm{c} . \mathrm{H}_{2} \mathrm{O}_{2}(\mathrm{HOOH})
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
03:00

Problem 68

Determine the geometry about each interior atom in each molecule
and draw the molecule. (Skeletal structure is indicated in parentheses.)
\begin{equation}\mathrm{ a. }{CH}_{3} \mathrm{NH}_{2}\left(\mathrm{H}_{3} \mathrm{CNH}_{2}\right)\end{equation}
\begin{equation}\mathrm{ b. }{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}\left(\mathrm{H}_{3} \mathrm{CCOOCH}_{3} \text { both } \mathrm{O} \text { atoms attached to second } \mathrm{C}\right)
\end{equation}\begin{equation}
\mathrm{ c. }{NH}_{2} \mathrm{CO}_{2} \mathrm{H}\left(\mathrm{H}_{2} \mathrm{NCOOH} \text { both } \mathrm{O} \text { atoms attached to } \mathrm{C}\right)
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
01:16

Problem 69

Explain why $\mathrm{CO}_{2}$ and $\mathrm{CCl}_{4}$ are both nonpolar even though they contain
polar bonds.

KC
Kara Cecil
Numerade Educator
01:22

Problem 70

$\mathrm{CH}_{3} \mathrm{F}$ is a polar molecule, even though the tetrahedral geometry often
leads to nonpolar molecules. Explain.

ES
Eugene Schneider
University of Minnesota - Twin Cities
02:44

Problem 71

Determine whether each molecule in Exercise 57 is polar or nonpolar.

Wilson Ma
Wilson Ma
The University of Alabama
04:44

Problem 72

Determine whether each molecule in Exercise 58 is polar or nonpolar.

Keenan Mintz
Keenan Mintz
University of Miami
02:10

Problem 73

Determine whether each molecule or ion is polar or nonpolar.
\begin{equation}\mathrm{ a. }{ClO}_{3}^{-} \quad \text { b. } \mathrm{SCl}_{2} \quad \text { c. } \mathrm{SCl}_{4} \quad\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
02:32

Problem 74

Determine whether each molecule is polar or nonpolar.
\begin{equation}\mathrm{ a. }{SiCl}_{4} \quad \text { b. } \mathrm{CF}_{2} \mathrm{Cl}_{2} \quad \text { c. SeF }_{6} \quad \text { d. IF }_{5}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
03:34

Problem 75

Each compound contains both ionic and covalent bonds. Write ionic
Lewis structures for each, including the covalent structure for the ion
in brackets. Write resonance structures if necessary.
\begin{equation}\begin{array}{lllll}{\text { a. } \mathrm{BaCO}_{3}} & {\text { b. } \mathrm{Ca}(\mathrm{OH})_{2}} & {\text { c. } \mathrm{KNO}_{3}} & {\text { d. LiIO }}\end{array}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
02:52

Problem 76

Each compound contains both ionic and covalent bonds. Write ionic
Lewis structures for each, including the covalent structure for the ion
in brackets. Write resonance structures if necessary.
\begin{equation}\mathrm{ a. }{RbIO}_{2} \quad \text { b. } \mathrm{NH}_{4} \mathrm{Cl} \quad \text { c. KOH } \quad \text { d. } \operatorname{Sr}(\mathrm{CN})_{2}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
02:00

Problem 77

Carbon ring structures are common in organic chemistry. Draw a
Lewis structure for each carbon ring structure, including any necessary
resonance structures.
\begin{equation}\mathrm{ a. }{C}_{4} \mathrm{H}_{8} \quad \text { b. } \mathrm{C}_{4} \mathrm{H}_{4}
\end{equation}\begin{equation}\mathrm{ c. }{C}_{6} \mathrm{H}_{12} \quad \text { d. } \mathrm{C}_{6} \mathrm{H}_{6}
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
00:50

Problem 78

Amino acids are the building blocks of proteins. The simplest amino
acid is glycine $\left(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH}\right) .$ Draw a Lewis structure for glycine. $($Hint : The central atoms in the skeletal structure are nitrogen bonded to carbon, which is bonded to another carbon. The two oxygen atoms are bonded directly to the rightmost carbon atom.)

Madi Sousa
Madi Sousa
Numerade Educator
02:35

Problem 79

Formic acid is partly responsible for the sting of ant bites. By mass,
formic acid is $26.10 \% \mathrm{C}, 4.38 \% \mathrm{H},$ and 69.5$\%$ O.The molar mass of
formic acid is 46.02 $\mathrm{g} / \mathrm{mol} .$ Find the molecular formula of formic acid
and draw its Lewis structure.

Madi Sousa
Madi Sousa
Numerade Educator
03:32

Problem 80

Diazomethane is a highly poisonous, explosive compound because it
readily evolves $N_{2} .$ Diazomethane has the following composition by
mass: $28.57 \% \mathrm{C} ; 4.80 \% \mathrm{H} ;$ and 66.64$\% \mathrm{N}$ . The molar mass of diazomethane is 42.04 $\mathrm{g} / \mathrm{mol} .$ Find the molecular formula of diazometh-
ane, draw its Lewis structure, and assign formal charges to each atom.
Why is diazomethane not very stable? Explain.

Madi Sousa
Madi Sousa
Numerade Educator
03:32

Problem 81

Draw the Lewis structure for nitric acid (the hydrogen atom is attached to one of the oxygen atoms). Include all three resonance structures by alternating the double bond among the three oxygen atoms.
Use formal charge to determine which of the resonance structures is most important to the structure of nitric acid.

Nadia Lara
Nadia Lara
Numerade Educator
01:41

Problem 82

Phosgene $\left(\mathrm{Cl}_{2} \mathrm{CO}\right)$ is a poisonous gas that was used as a chemical
weapon during World War I. It is a potential agent for chemical terrorism today. Draw the Lewis structure of phosgene. Include all three resonance forms by alternating the double bond among the three terminal atoms. Which resonance structure is the best?

Tiffany Noble
Tiffany Noble
Numerade Educator
02:58

Problem 83

The cyanate ion $\left(\mathrm{OCN}^{-}\right)$ and the fulminate ion $\left(\mathrm{CNO}^{-}\right)$ share the same three atoms, but have vastly different properties. The cyanate ion is stable, while the fulminate ion is unstable and forms explosive compounds. The resonance structures of the cyanate ion were explored in pounds. The resonance structures of the cyanate ion were explosive com
Example $6.6 .$ Draw Lewis structures for the fulminate ion-including possible resonance forms $-$ and use formal charge to explain why the fulminate ion is less stable (and therefore more reactive) than the cyanate ion.

Madi Sousa
Madi Sousa
Numerade Educator
03:20

Problem 84

Draw the Lewis structure for each organic compound from its condensed structural formula.
\begin{equation}\mathrm{a} \cdot \mathrm{C}_{3} \mathrm{H}_{8} \quad \text { b. } \mathrm{CH}_{3} \mathrm{OCH}_{3} \text { c. } \mathrm{CH}_{3} \mathrm{COCH}_{3}
\end{equation}\begin{equation}\mathrm{d} . \mathrm{CH}_{3} \mathrm{COOH} \quad \text { e. } \mathrm{CH}_{3} \mathrm{CHO}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
03:00

Problem 85

Draw the Lewis structure for each organic compound from its condensed structural formula.
\begin{equation}\mathrm{ a. }{C}_{2} \mathrm{H}_{4} \quad \text { b. } \mathrm{CH}_{3} \mathrm{NH}_{2} \quad\mathrm{ c. }{HCHO}\end{equation}\begin{equation}
\mathrm{ d. }{CH}_{3} \mathrm{COOH} \text { e. } \mathrm{CH}_{3} \mathrm{CHO}
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
01:45

Problem 86

Use Lewis structures to explain why $\mathrm{Br}_{3}^{-}$ and $\mathrm{I}_{3}^{-}$ are stable, while $\mathrm{F}_{3}^{-}$ is not.

Tiffany Noble
Tiffany Noble
Numerade Educator
View

Problem 87

Draw the Lewis structure for $\mathrm{HCSNH}_{2} .$ (The carbon and nitrogen
atoms are bonded together, and the sulfur atom is bonded to the carbon atom.) Label each bond in the molecule as polar or nonpolar.

Stephanie Castillo
Stephanie Castillo
Numerade Educator
01:41

Problem 88

Draw the Lewis structure for urea, $\mathrm{H}_{2} \mathrm{NCONH}_{2},$ one of the compounds
responsible for the smell of urine. (The central carbon atom is bonded to
both nitrogen atoms and to the oxygen atom.) Does urea contain polar
bonds? Which bond in urea is most polar?

Tiffany Noble
Tiffany Noble
Numerade Educator
02:11

Problem 89

Some theories of aging suggest that free radicals cause certain diseases and perhaps aging in general. As you know from the Lewis model, such molecules are not chemically stable and will quickly react with other molecules. According to some theories, free radicals may attack molecules within the cell, such as DNA, changing them and causing cancer or other diseases. Free radicals may also attack molecules on the surfaces of cells, making them appear foreign to the body's immune system. The immune system then attacks the cells and destroys them,weakening the body. Draw Lewis structures for the free radicals implicated in this theory of aging, which are given here.
\begin{equation}\mathrm{ a. }{O}_{2}^{-} \quad \text { b. } \mathrm{O}^{-} \quad \text { c. } \mathrm{OH}\end{equation}\begin{equation}\mathrm{d} . \mathrm{CH}_{3} \mathrm{OO} \quad \text(unpaired\ electron\ on\ terminal\ oxygen)
\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
01:24

Problem 90

Free radicals are important in many environmentally significant reactions. For example, photochemical smog-smog that results from the action of sunlight on air pollutants - forms in part by these two steps:
$$\begin{array}{c}{\mathrm{NO}_{2} \stackrel{\mathrm{UV} \text { light }}{\longrightarrow} \mathrm{NO}+\mathrm{O}} \\ {\mathrm{O}+\mathrm{O}_{2} \quad \longrightarrow \mathrm{O}_{3}}\end{array}$$
The product of this reaction, ozone, is a pollutant in the lower atmosphere. (Upper atmospheric ozone is a natural part of the atmosphere that protects life on Earth from ultraviolet light.) Ozone is an eye and lung irritant and also accelerates the weathering of rubber products. Rewrite the above reactions using the Lewis structure of each reactant and product. Identify the free radicals.

Madi Sousa
Madi Sousa
Numerade Educator
02:05

Problem 91

A compound composed of only carbon and hydrogen is 7.743$\%$ hydrogen by mass. Draw a Lewis structure for the compound.

Madi Sousa
Madi Sousa
Numerade Educator
02:16

Problem 92

A compound composed of only carbon and chlorine is 85.5$\%$ chlorine
by mass. Draw a Lewis structure for the compound.

Madi Sousa
Madi Sousa
Numerade Educator
13:37

Problem 93

Amino acids are biological compounds that link together to form proteins, the workhorse molecules in living organisms. The skeletal structures of several simple amino acids are shown here. For each skeletal structure,complete the Lewis structure, determine the geometry about each interior
atom, and draw the molecule, using the bond conventions of Section $6.9 .$

Keenan Mintz
Keenan Mintz
University of Miami
05:37

Problem 94

The genetic code is based on four different bases with the structures
shown here. Assign a geometry to each interior atom in these four bases.
\begin{equation}\quad \text { a. cytosine } \quad \text { b. adenine } \quad \text { c. thymine } \quad \text { d. guanine }\quad\end{equation}

David Collins
David Collins
Numerade Educator
02:10

Problem 95

Most vitamins can be classified either as fat soluble, which results in their
tendency to accumulate in the body (so that taking too much can be
harmful), or water soluble, which results in their tendency to be quickly eliminated from the body in urine. Examine the structural formulas and
space-filling models of these vitamins and determine whether each one is
fat soluble (mostly nonpolar) or water soluble (mostly polar).
\begin{equation}\mathrm \quad \text {a. vitamin C} \quad \text{b. vitamin A} \quad \text{c. niacin (vitamin B3)} \quad \text {d. vitamin E} \end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
02:17

Problem 96

Water alone does not easily remove grease from dishes or hands because grease is nonpolar and water is polar. The addition of soap to water, however, allows the grease to dissolve. Study the structure of sodium stearate (a soap) and describe how it works.

Madi Sousa
Madi Sousa
Numerade Educator
01:49

Problem 97

The azide ion, $\mathrm{N}_{3}^{-},$ is a symmetrical ion and all of its contributing
resonance structures have formal charges. Draw three important contributing structures for this ion.

Madi Sousa
Madi Sousa
Numerade Educator
02:29

Problem 98

A 0.167 -g sample of an unknown compound contains 0.00278 $\mathrm{mol}$
of the compound. Elemental analysis of the compound gives the following percentages by mass: $40.00 \% \mathrm{C} ; 6.71 \% \mathrm{H} ; 53.29 \%$ O. Determine the molecular formula, molar mass, and Lewis structure of the unknown compound.

Wilson Ma
Wilson Ma
The University of Alabama
04:21

Problem 99

Use the dipole moments of $\mathrm{HF}$ and $\mathrm{HCl}$ (given at the end of the
problem) together with the percent ionic character of each bond (Figure 6.5) to estimate the bond length in each molecule. How well does your estimated bond length agree with the bond length in Table 6.4$?$
$$\begin{aligned} \mathrm{HCl} \mu &=1.08 \mathrm{D} \\ \mathrm{HF} \mu &=1.82 \mathrm{D} \end{aligned}$$

David Collins
David Collins
Numerade Educator
02:46

Problem 100

One form of phosphorus exists as $P_{4}$ molecules. Each $P_{4}$ molecule has
four equivalent $P$ atoms, no double or triple bonds, and no expanded
octets. Draw the Lewis structure for $P_{4} .$

Bryan Li
Bryan Li
Numerade Educator
01:22

Problem 101

A compound has the formula $\mathrm{C}_{8} \mathrm{H}_{8}$ and does not contain any double or
triple bonds. All the carbon atoms are chemically identical, as are all the
hydrogen atoms. Draw the Lewis structure for this molecule.

Tiffany Noble
Tiffany Noble
Numerade Educator
00:46

Problem 102

The species $\mathrm{NO}_{2}, \mathrm{NO}_{2}^{+},$ and $\mathrm{NO}_{2}^{-},$ in which $\mathrm{N}$ is the central atom,
have very different bond angles. Predict what these bond angles might
be with respect to the ideal angles and justify your prediction.

Lottie Adams
Lottie Adams
Numerade Educator
01:25

Problem 103

The bond angles increase steadily in the series $\mathrm{PF}_{3}, \mathrm{PCl}_{3}, \mathrm{PBr}_{3},$ and $\mathrm{Pl}_{3} .$ After consulting the data on atomic radii in Chapter $4,$ provide an
explanation for this observation.

Madi Sousa
Madi Sousa
Numerade Educator
16:43

Problem 104

Draw the Lewis structure for acetamide $\left(\mathrm{CH}_{3} \mathrm{CONH}_{2}\right),$ an organic
compound, and determine the geometry about each interior atom. Experiments show that the geometry about the nitrogen atom in acetamide is nearly planar. Which resonance structure can account for the
planar geometry about the nitrogen atom?

Erin Wagner
Erin Wagner
Numerade Educator
02:59

Problem 105

Use VSEPR to predict the geometry (including bond angles) about each
interior atom of methyl azide $\left(\mathrm{CH}_{3} \mathrm{N}_{3}\right)$ and draw the molecule. Would you expect the bond angle between the two interior nitrogen atoms to
be the same or different? Would you expect the two nitrogen-nitrogen
bond lengths to be the same or different?

Madi Sousa
Madi Sousa
Numerade Educator
01:57

Problem 106

In the very first chapter of this book, we described the scientific approach and put a special emphasis on scientific models or theories. In this chapter, we looked carefully at the Lewis model of chemical
bonding. Why is this theory successful? What are some of the limitations of the theory

Anatole Borisov
Anatole Borisov
Numerade Educator
01:29

Problem 107

Which statement best captures the fundamental idea behind VSEPR
theory? Explain what is wrong with the statements you do not
choose.
\begin{equation}\begin{array}{l}{\text { a. The angle between two or more bonds is determined primarily by }} \\ {\text { the repulsions between the electrons within those bonds and other }} \\ {\text { (lone pair) electrons on the central atom of a molecule. Each of these electron groups }} \\ {\text { (bonding electrons or lone pair electrons)lowers its potential energy by maximizing }} \\ {\text { its separation from other electron groups, thus determining the geometry of the molecule. }} \\ {\text { b. The angle between two or more bonds is determined primarily by the repulsions between }} \\ {\text { the electrons within those bonds. Each of these bonding electrons lowers its potential energy }} \\ {\text { by maximizing its separation from other electron groups, thus determining the geometry }} \\ {\text { of the molecule }} \\ {\text { c. The geometry of a molecule is determined by the shapes of the overlapping orbitals }} \\ {\text { that form the chemical bonds. Therefore, to determine the geometry of a molecule, }} \\ {\text { you must determine the shapes of the orbitals involved in bonding.}}\end{array}\end{equation}

Madi Sousa
Madi Sousa
Numerade Educator
01:10

Problem 108

Suppose that a molecule has four bonding groups and one lone pair on the central atom. Suppose further that the molecule is confined to two dimensions (this is a purely hypothetical assumption for the sake of understanding the principles behind VSEPR theory). Draw the molecule
and estimate the bond angles.

Wilson Ma
Wilson Ma
The University of Alabama