Deck 1: Introduction and Review

Question 1

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?

Answer 1

Compounds synthesized from petroleum products have a lower content of ¹⁴C. Plant-derived compounds are recently synthesized from CO₂ in the air and have a higher ¹⁴C content.

Question 2

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

Answer 2

oxygen

Question 3

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

Answer 3

isotopes

Question 4

An oxygen atom has ________ valence electrons.

Question 5

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

Question 6

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 7

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 8

Draw the line energy orbital diagram for the outer shell of an uncharge nitrogen atom and describe the location and number of unshared electrons.

Question 9

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 10

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

Question 11

The electron density of ________ orbitals has spherical symmetry.

Question 12

Draw the Lewis structure for 2-butanol, CH₃CH(OH)CH₂CH₃.

Question 13

Draw the shape of a 2p orbital.

Question 14

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

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

Question 15

The element with the electronic configuration 1s²2s²2p⁶3s¹ is ________.

Question 16

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 17

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

Question 18

Draw a correct Lewis structure for chloromethane, CH₃Cl.

Question 19

Provide the electron configuration of phosphorus.

Question 20

Draw the Lewis structure of acetic acid, CH₃CO₂H.

Question 21

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

Question 22

Assign the correct formal charge to each nitrogen atom in the following Lewis structure.

Question 23

Draw a proper Lewis structure for H₂SO₄.

Question 24

Add the appropriate formal charge to each atom in the molecule below. It is not necessary to indicate formal charges when zero.

Question 25

One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure and indicate any such charges.

Question 26

Draw a correct Lewis structure for acetonitrile, CH₃CN.

Question 27

Add the appropriate formal charge to each atom in the molecule below. It is not necessary to indicate formal charges when zero.

Question 28

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

Question 29

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 30

Draw a correct Lewis structure for boric acid, B(OH)₃.

Question 31

Which of the following molecules contains a polar covalent bond?

A) H₂
B) F₂
C) CH₃Cl
D) NaCl
E) He

Question 32

Draw a correct Lewis structure for tert-butyl alcohol, (CH₃)₃COH.

Question 33

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

Question 34

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

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

Question 35

The formal charge on nitrogen in the compound below is ________.

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

Question 36

One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure and indicate any such charges.

Question 37

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 38

Which of the following are correct 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 39

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

Question 40

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) uncharged
D) slightly negative
E) -1

Question 41

Draw the other important resonance form of:

Question 42

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 43

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 44

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 45

Draw the important resonance forms for the structure shown below.

Question 46

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

Question 47

Draw the important resonance forms for the structure shown below.

Question 48

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 49

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

Question 50

Draw the important resonance forms of:

Question 51

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

Question 52

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

Question 53

Draw the important resonance forms for the structure shown below.

Question 54

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

Question 55

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 56

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 57

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 58

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

A)
B)
C)
D)

Question 59

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

Question 60

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 61

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

Question 62

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

Question 63

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

Question 64

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

Question 65

How many carbon atoms are present in the molecule shown?

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

Question 66

Draw condensed structures for the four compounds with formula C₃H₉N.

Question 67

Draw a correct Lewis structure for (CH₃)₂CHCOOH.

Question 68

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

Question 69

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

A)

B)

C)

D)

Question 70

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

Question 71

How many hydrogen atoms are present in the molecule shown?

Question 72

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

Question 73

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

Question 74

Provide the line-angle formula (skeletal structure) for CH₂=CHCH₂CH₂C(CH₃)₃.

Question 75

Provide the structural formula for an aldehyde whose condensed structure is (CH₃)₃CCHO.

Question 76

Draw a correct Lewis structure for acetaldehyde, CH₃CHO.

Question 77

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 78

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

Question 79

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 80

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