Deck 1: Structure and Bonding

Question 1

The formal charge on the nitrogen on the structure shown below is:

Answer 1

N = +1

Question 2

Provide the electron configuration of phosphorus.

Answer 2

1s²2s²2p⁶3s²3p³

Question 3

Draw the Lewis structure for 2-propanol, CH₃CH(OH)CH₃, including all non-bonding lone pairs.

Answer 3

Question 4

The electron density of ________ orbitals has spherical symmetry.

Question 5

How many distinct p orbitals exist in the second electron shell, where n = 2?

A) 2
B) 3
C) 4
D) 5
E) 6

Question 6

A node is a region of high electron density between the two atoms in a covalent bond.

Question 7

Draw the shape of a 2p orbital, including shading to indicate phase.

Question 8

Which element in the second row of the periodic table has six valence electrons and a valence of two?

Question 9

Provide a Lewis structure for a molecule with molecular formula CH₂O₂.

Question 10

In a carbon atom, the 2s and 2p orbitals are the same energy.

Question 11

Atoms with the same number of protons but different numbers of neutrons are called ________.

Question 12

Draw the Lewis structure of acetic acid, CH₃CO₂H, including all non-bonding lone pairs.

Question 13

The ________ tells us that each orbital can hold a maximum of 2 electrons.

A) aufbau principle
B) Pauli exclusion principle
C) Hund's rule principle
D) LeChatelier principle
E) uncertainty principle

Question 14

The atomic number of boron is 5. The correct electronic configuration of boron is:

A) 1s²2s³
B) 1s²2p³
C) 1s²2s²2p¹
D) 2s²2p³
E) 1s²2s²3s¹

Question 15

While you were up late one night studying organic chemistry, you happened to see the last 5 minutes of an infomercial on TV. The spokesperson claimed that their brand of automobile tires were superior to all other brands on the market because they were made by using only natural rubber, isolated from the resin of rubber trees. How could a chemist test her claims that no petroleum products went into the manufacture of her brand of tires?

Question 16

An oxygen atom has ________ valence electrons.

Question 17

Orbitals which are equal in energy are referred to as ________.

A) degenerate
B) polar
C) nodes
D) filled
E) nonpolar

Question 18

When filling two or more orbitals of the same energy with electrons, the electrons will go into different orbitals rather than pair up in the same orbital.

Question 19

Draw a correct Lewis structure for chloromethane, CH₃Cl, including all non-bonding lone pairs.

Question 20

The element with the electronic configuration 1s²2s²2p⁶3s¹ is ________.

Question 21

Add the appropriate formal charge to each atom in the molecule below. It is not necessary to indicate formal charges when zero. (All non-bonding electrons are included.)

Question 22

The formal charge on the oxygens in the compound below are ________.

A) Oxygen 1: 0, Oxygen 2: 0
B) Oxygen 1: -1, Oxygen 2: 0
C) Oxygen 1: 0, Oxygen 2: -1
D) Oxygen 1: +1, Oxygen 2: 0
E) Oxygen 1: -1, Oxygen 2: -1

Question 23

Add the appropriate formal charge to each atom in the molecule below. It is not necessary to indicate formal charges when zero. (All non-bonding electrons are included.)

Question 24

One or more of the atoms in the structure shown should have nonzero formal charges. Add the correct formal charge/s. (All non-bonding electrons have been included.)

Question 25

The formal charge on oxygen in dimethyl ether, CH₃OCH₃, is ________.

A) +2
B) +1
C) 0
D) -1
E) -2

Question 26

Draw a correct Lewis structure for acetonitrile, CH₃CN, including all non-bonding lone pairs.

Question 27

Draw 2 possible Lewis structures for the compound with molecular formula C₃H₆.

Question 28

For most compounds in which a nitrogen atom bears no formal charge, the valence of this nitrogen atom is ________.

Question 29

Assign the correct formal charge to each nitrogen atom in the following Lewis structure. (All non-bonding electrons are included.)

Question 30

One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure and the atoms with non-zero formal charges.

Question 31

The electronegativity of elements on the periodic table increases going ________ a column and to the ________ in each row.

A) up; right
B) up; left
C) down; right
D) down; left

Question 32

Which of the following molecules contains a polar covalent bond?

A) H₂
B) F₂
C) CH₃Cl
D) NaCl
E) He

Question 33

A carbon-hydrogen bond in ethane (CH₃CH₃) is best described a ________.

A) highly polar
B) essentially nonpolar
C) ionic
D) a multiple bond
E) resonance stabilized

Question 34

Which of the following are acceptable Lewis structures, including formal charges, for nitric acid, HNO₃?

A) A only
B) B only
C) C only
D) both B and C
E) A, B, and C

Question 35

Draw a correct Lewis structure for tert-butyl alcohol, (CH₃)₃COH, including all non-bonding lone pairs.

Question 36

Covalent bonds may be polar or nonpolar. What property of the atoms forming a given bond determines this?

Question 37

Draw the Lewis structure for boric acid, B(OH)₃, including all non-bonding lone pairs.

Question 38

Within a given row of the periodic table, electronegativity typically increases left to right across the row.

Question 39

The compound methylamine, CH₃NH₂, contains a C-N bond. In this bond, which of the following best describes the charge on the carbon atom?

A) +1
B) slightly positive
C) neutral
D) slightly negative
E) -1

Question 40

Write a Lewis structure for a compound with the molecular formula H₂N₂.

Question 41

The Lewis structure of trimethylamine is shown below. Draw the condensed structural formula which corresponds to this Lewis structure.

Question 42

Nitroamines are common functional groups found in energetic materials, such as RDX and HMX. For the structure below, draw two other significant resonance structures, include any formal charges, and indicate the hybridization on each nitrogen and oxygen.

Question 43

Which of the following compounds are covalent compounds?

A) KCl
B) CF₄
C) NH₃
D) both A and B
E) both B and C

Question 44

When a negatively charged species is most appropriately depicted as a hybrid of several resonance forms, the negative charge present is considered to be rapidly moving between the resonance forms bearing the formal negative charge.

Question 45

Structures ________, shown below, are resonance structures, and structure ________ is the major contributor to the overall resonance hybrid.

A) 2 & 4; 2
B) 1, 3 & 5; 3
C) 4 & 6; 6
D) 1, 3 & 5; 1
E) 1, 3, 4 & 5; 3

Question 46

Draw the important resonance forms for the structure shown below.

Question 47

In the compound sodium methoxide (NaOCH₃), there is ________ bonding.

A) ionic
B) polar covalent
C) nonpolar covalent
D) a mixture of ionic and covalent
E) resonance stabilized

Question 48

Draw the complete Lewis structure for the compound whose condensed formula is (CH₃)₂CHCHO.

Question 49

One resonance structure of a cation is shown. Provide the other reasonable resonance structures.

Question 50

Draw the other important resonance form of:

Question 51

Draw a line-angle formula for (CH₃)₂CHCH₂CH₂NH₂.

Question 52

Which of the following structures (a-d) is another resonance structure of the following organic molecule?

A)
B)
C)
D)

Question 53

When a molecule can best be represented as a series of resonance forms, each of these forms always contributes to the same degree in the hybrid.

Question 54

The Lewis structure of pentane is shown below. Draw the condensed structural formula which corresponds to this Lewis structure.

Question 55

Draw 3 significant resonance structures for the compound shown below. Place a box around the major contributor. Fill in any missing formal charges.

Question 56

Draw additional resonance contributors for:

Question 57

Which of the following bonding patterns of carbon is not allowed in the formation of an organic compound?

A)
B)
C)
D)
E)
F)

Question 58

Draw the important resonance forms for the structure shown below.

Question 59

Which of the following choices represent(s) a pair of resonance forms?

A)
B)
C)
D) both A and C
E) both B and C

Question 60

Draw the important resonance forms of the structure below to indicate the delocalization of charge. Indicate which is the major contributor to the overall structure.

Question 61

Draw the line-angle formula for three compounds with molecular formula C₃H₈O.

Question 62

What is the molecular formula for the following line-angle structure?

Question 63

Which of the following condensed formulas correctly represents the line-angle structure shown below?

A) CH(CH₃)₂CH(CH₃)CO₂H
B) C₂(CH₃)₃CO₂H
C) (CH₃)₂CC(CH₃)CO₂H
D) C(CH₃)₂C(CH₃)CH₂CO₂H

Question 64

Provide the line-angle formula (skeletal structure) for (CH₃)₂CHCH₂CHO.

Question 65

Which of the following condensed formulas represents the same compound as the line-angle structure shown?

A) CH₃CH₂CH₂OCH₂CH₂CH₂N(CH₂CH₂CH₃)₂
B) CH₃CH₂CH₂OCH₂N(CH₂CH₃)₂
C) CH₃CH₂OCH₂N(CH₂CH₃)₂
D) CH₃CH₂OCH₂N(CH₂CH₂CH₃)₂
E) CH₃ON(CH₃)₂

Question 66

How many carbon atoms are present in the molecule shown?

A) 6
B) 8
C) 10
D) 11
E) 12

Question 67

A condensed structure for acetone is CH₃COCH₃. Provide the structural formula for acetone.

Question 68

Draw a correct Lewis structure for CH₃CHCHCOOH.

Question 69

Draw an acceptable line-angle formula for the compound shown below.

Question 70

Provide the line-angle formula (skeletal structure) for (CH₃CH₂)₂C=O.

Question 71

How many hydrogen atoms are present in the molecule shown?

Question 72

Draw a correct Lewis structure for acetaldehyde, CH₃CHO.

Question 73

Compute the empirical and molecular formulas for the compound of molecular weight 180 g/mol which is shown to contain 40.0% C and 6.7% H by elemental analysis.

Question 74

Provide the line-angle formula for the alcohol CH₃CH₂CH(OH)CH₂CH₂CH(CH₃)₂.

Question 75

Provide the line-angle formula for CH₃CH₂C(CH₃)₂CH₂CHO

Question 76

Draw an acceptable line-angle formula for cyclobutanol (shown below).

Question 77

What is the molecular formula for the following line-angle structure?

Question 78

Draw a complete Lewis structure, including lone pairs, for (CH₃)₂CHCO₂H.

Question 79

Draw condensed structures for the four compounds with formula C₃H₉N.

Question 80

Indicate the line-angle structure that corresponds to the condensed structure, HOCH₂C(O)CH(CH₃)₂.

A)
B)
C)
D)