1. What is the ground state electron configuration of carbon?

2 2
A. 1s 2s 2px1
2 2
B. 1s 2s 2px2
2 2
C. 1s 2s 2px12py1
2 2
D. 1s 2s 2px22py1

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.01
Subtopic: Periodic table trends
Topic: Structure and Bonding

2. Which of the following has (have) the same electron configuration as Ne?

- 2+ 2- +
Na Mg O Mg

- 2-
A. Na and O
2+ 2-
B. Mg and O
+ 2-
C. Mg and O
2+
D. only Mg

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.02
Subtopic: Periodic table trends
Topic: Structure and Bonding
3. What is the letter designation given to dumbbell shaped orbitals like the one depicted
below?

A. s
B. p
C. d
D. f

Bloom's Level: 1. Remember

Chapter: 01
Difficulty: Easy
Gradable: automatic
Section: 01.01
Subtopic: Atomic orbitals
Topic: Molecular Shape

4. Which of the following atoms has vacant d orbitals that permit it to accommodate more
than eight electrons in its valence shell?
A. N
B. C
C. Ne
D. S

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Easy
Gradable: automatic
Section: 01.08
Subtopic: Octet rule exceptions
Topic: Structure and Bonding

5. Predict which bond is the most polar in ethanol, CH 3CH2OH?

A. C-C
B. C-H
C. C-O
D. O-H

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.04
Subtopic: Bond properties
Subtopic: Types of bonds
Topic: Structure and Bonding
6. Which one of the following is the conjugate base of NH 3?

A. NH4+
+
B. H
C. N3-
-
D. NH2

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.12
Subtopic: Acid/Base definitions
Topic: Acids and Bases

7. What can be said about the polarity of the C=O bond?

A. C and O have the same electronegativity; the bond is nonpolar

B. the C=O bond is polar; the O atom bears a partial negative charge
C. the C=O bond is nonpolar; the C atom bears a partial positive charge
D. the C=O bond is polar; the C atom bears a partial negative charge

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.04
Subtopic: Bond properties
Subtopic: Types of bonds
Topic: Structure and Bonding
8. Identify the condensed formula of the following structure:

A. (CH3)2CHCHClCH(CH3)2

B. CH3CH(CH3)CHClCH(CH3)2
C. (CH3)2CHCHClC(CH3)3
D. (CH3)3CCHClCH(CH3)3

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Condensed formula
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules

9. What is the chemical formula of the following carbon skeleton diagram?

A. C8H14
B. C8H16
C. C8H18
D. C8H20

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Easy
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
10. How many hydrogen atoms are there on carbon atoms 1 and 2, respectively, in the
structure below?

A. 4, 1
B. 4, 0
C. 3, 1
D. 3, 0

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules

11. How many C3H8O constitutional isomers are possible?

A. one
B. two
C. three
D. four

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Constitutional isomers
Topic: Drawing Organic Molecules
12. Which of the following best describes the relationship between the two structures?

A. identical compounds
B. resonance structures
C. constitutional isomers
D. different compounds with different constitutions

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules

13. How many constitutional isomers of C 4H9Br are possible?

A. one
B. two
C. three
D. four

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Constitutional isomers
Topic: Drawing Organic Molecules

14. How many constitutional isomers of C 3H6Cl2 are possible?

A. three
B. four
C. five
D. six

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Constitutional isomers
Topic: Drawing Organic Molecules
15. What is the formal charge on the carbon atom?

A. +1
B. 0
C. -1
D. -2

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding

16. Which of the following describes the relationship between the following two structures?

A. identical structures
B. resonance forms
C. constitutional isomers
D. different compounds with different compositions

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
17. Which of the following describes the relationship between the following two ions?

A. identical structures
B. resonance forms
C. constitutional isomers
D. different compounds with different compositions

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Easy
Gradable: automatic
Section: 01.07
Subtopic: Resonance
Topic: Structure and Bonding

18. What is the formal charge on the oxygen atom in the structure below?

A. -1
B. 0
C. +1
D. +2

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding
19. What is the formal charge on the nitrogen atom in the structure below?

A. -1
B. 0
C. +1
D. +2

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding

20. The formal charges on the nitrogen and oxygen in the following structures are,
respectively

A. +1, -1
B. 0, -1
C. +1, 0
D. 0, 0

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding
21. In which of the following compounds would you expect Cl to have a partial
positive charge?
A. HCl
B. CCl4
C. NaCl
D. HOCl

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.04
Subtopic: Bond properties
Subtopic: Types of bonds
Topic: Structure and Bonding

22. Based on the VSEPR model, which of the following species has (have) a trigonal planar
geometry?
I. BCl3 II. NH3 III. NO3¯

A. only I
B. I and II
C. I and III
D. I, II, and III

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.09
Subtopic: VSEPR theory
Topic: Molecular Shape

23. Based on VSEPR theory, which of the following species has (have) a trigonal pyramidal
geometry?
I. CO32- II. NH3 III. CH3+

A. only I
B. only II
C. I and II
D. II and III

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.09
Subtopic: VSEPR theory
Topic: Molecular Shape
24. Which of the following species has(have) a linear geometry?
I. CO2 II. NO2 + III. NO2¯

A. only I
B. only II
C. I and II
D. I, II, and III

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.09
Subtopic: VSEPR theory
Topic: Molecular Shape

25. Which of the following molecules would you expect to have a dipole moment?
I. CO2 II. HCN III. CHCl3

A. II and III
B. only II
C. only III
D. I, II, and III

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.10
Subtopic: Dipole moments
Subtopic: Polarity of molecules
Topic: Molecular Shape
26. Which of the following molecules would you expect to have a dipole moment?
I. CH2Cl2 II. CH3Cl III. CCl4

A. only I
B. only II
C. I and II
D. I, II, and III

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.10
Subtopic: Dipole moments
Subtopic: Polarity of molecules
Topic: Molecular Shape

27. The H-C-H bond angles in ethylene, C2H4, are closest to

A. 90°.
B. 109.5°.
C. 120°.
D. 180°.

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.09
Subtopic: Hybridization
Topic: Molecular Shape

28. The C-C-C bond angle in propane, C3H8, is closest to

A. 90°.
B. 109.5°.
C. 120°.
D. 180°.

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.09
Subtopic: Hybridization
Topic: Molecular Shape
29. What are the formal charges of boron and nitrogen, respectively, in the following
structure?

A. -1 and +1
B. -1 and 0
C. 0 and +1
D. 0 and 0

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding

30. Which one of the following is isoelectronic with CO 2?

A. NO2¯
B. NO2+
C. NO2
D. O3

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.10
Subtopic: Dipole moments
Subtopic: Polarity of molecules
Subtopic: VSEPR theory
Topic: Molecular Shape
31. In which of the following does hydrogen have a partial negative charge based
on electronegativity?
A. BH3
B. CH4
C. NH3
D. H2O

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.04
Subtopic: Bond properties
Subtopic: Types of bonds
Topic: Structure and Bonding

32. Which of the following species have a zero formal charge on its carbon atom?

A. I and II
B. II and IV
C. III and IV
D. I, II, and III

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding
33. Which one of the following species is formed when diazomethane loses a nitrogen
molecule?

diazomethane

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.11
Subtopic: Bond formation and bond breaking
Subtopic: Drawing and interpretation
Topic: Curved Arrows
 +
34. Which species is formed when the CH3N2 cation loses a nitrogen molecule?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.11
Subtopic: Bond formation and bond breaking
Subtopic: Drawing and interpretation
Topic: Curved Arrows
35. Give the molecular formula of the compound shown below:

A. C8H16O
B. C9H18O
C. C10H18O
D. C10H20O

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
36. The electron pair movement depicted below produces a second resonance form for the
species. What is the formal charge on the nitrogen atom for this second resonance form?

A. -2
B. -1
C. 0
D. +1

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.07
Subtopic: Bond formation and bond breaking
Subtopic: Drawing and interpretation
Subtopic: Formal charges
Subtopic: Resonance
Topic: Curved Arrows
Topic: Structure and Bonding

37. Which statement correctly describes the structures of BH 3 and NH3?

A. Both are trigonal and planar.

B. Both are pyramidal.
C. BH3 is trigonal planar and NH3 is trigonal pyramidal.
D. BH3 is trigonal pyramidal and NH3 is trigonal planar.

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Bloom's Level: 3. Apply
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.09
Subtopic: VSEPR theory
Topic: Molecular Shape
38. Which one of the following is the conjugate acid of ethanol?
-
A. CH3CH2O
+
B. CH3CH2O
C. CH3CH2OH2+
D. CH3CH2OH3+

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Bloom's Level: 2. Understand
Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.12
Subtopic: Acid/Base definitions
Topic: Acids and Bases

39. In the equilibrium below, the strongest base is: (pK a H2O = 15.7, pKa NH3 = 36)

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.14
Subtopic: Predicting acid/base reaction equilibrium
Topic: Acids and Bases
40. In the equilibrium below, the strongest acid is:

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.14
Subtopic: Factors affecting acid strength
Subtopic: Predicting acid/base reaction equilibrium
Topic: Acids and Bases
41. Which one of the following is the strongest base?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.13
Subtopic: Factors affecting acid strength
Topic: Acids and Bases
42. Which one of the following mechanistically depicts the protonation of methanol by
hydrogen bromide?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.11
Subtopic: Curved arrow notation
Topic: Curved Arrows
43. Which one of the following is the strongest acid?

A. FCH2CO2H
B. ClCH2CO2H
C. BrCH2CO2H
D. ICH2CO2H

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.13
Subtopic: Factors affecting acid strength
Topic: Acids and Bases

44. Which one of the following has the largest acid equilibrium constant, K a?

A. CH3CO2H
B. CH2ClCO2H
C. CHCl2CO2H
D. CCl3CO2H

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Bloom's Level: 4. Analyze
Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.13
Subtopic: Factors affecting acid strength
Subtopic: pKa
Topic: Acids and Bases
45. For which of the following does the equilibrium favor reactants?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.14
Subtopic: Predicting acid/base reaction equilibrium
Topic: Acids and Bases
46. Identify the resonance structure that results from the following "electron pair
movements."

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.07
Subtopic: Resonance
Topic: Structure and Bonding
47. A Lewis structure of the azide ion, N 3¯, is shown below. The formal charge on the middle
nitrogen atom is:

A. +2
B. +1
C. 0
D. -1

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding
48. Identify the species that results from the following movement of electron pairs.

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.11
Subtopic: Bond formation and bond breaking
Subtopic: Curved arrow notation
Subtopic: Drawing and interpretation
Topic: Curved Arrows
49. The most stable resonance contributor of this would be:

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.07
Subtopic: Resonance
Topic: Structure and Bonding
50. What is the molecular formula of aspirin?

A. C6H4O4
B. C8H8O4
C. C9H8O4
D. C9H10O4

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules

51. Which of the following is not identical to the others?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Easy
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
52. Which of the line-bond structures below cannot represent a stable molecule?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
53. Which of the electron-movement arrows below are NOT valid?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.07
Subtopic: Resonance
Topic: Structure and Bonding
54. What atom would have a formal charge in this structure?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.05
Subtopic: Formal charges
Topic: Structure and Bonding
55. Rank the following in order of decreasing acidity. (more acidic > less acidic)

A. I > IV > III > II

B. IV > I > II > III
C. III > II > I > IV
D. I > III > IV > II

Bloom's Level: 4. Analyze

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.13
Subtopic: Acid/Base definitions
Subtopic: Factors affecting acid strength
Topic: Acids and Bases
56. Using resonance principles, what atom is acid first protonated in the molecule shown?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 01
Difficulty: Hard
Gradable: automatic
Section: 01.13
Subtopic: Acid/Base definitions
Subtopic: Factors affecting acid strength
Subtopic: Resonance
Topic: Acids and Bases
Topic: Structure and Bonding
57. What structure would result from these electron movement arrows?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.07
Subtopic: Bond formation and bond breaking
Subtopic: Curved arrow notation
Subtopic: Drawing and interpretation
Topic: Curved Arrows
58. What would be the line-bond structure for (CH3)3CCH2CH(CH3)2?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 01
Difficulty: Medium
Gradable: automatic
Section: 01.06
Subtopic: Condensed formula
Subtopic: Skeletal/bond-line structures
Topic: Drawing Organic Molecules
 Category # of Questions
Accessibility: Keyboard Navigation 23
Bloom's Level: 1. Remember 1
Bloom's Level: 2. Understand 23
Bloom's Level: 3. Apply 23
Bloom's Level: 4. Analyze 11
Chapter: 01 58
Difficulty: Easy 5
Difficulty: Hard 16
Difficulty: Medium 37
Gradable: automatic 58
Section: 01.01 2
Section: 01.02 1
Section: 01.04 4
Section: 01.05 8
Section: 01.06 13
Section: 01.07 6
Section: 01.08 1
Section: 01.09 6
Section: 01.10 3
Section: 01.11 4
Section: 01.12 2
Section: 01.13 5
Section: 01.14 3
Subtopic: Acid/Base definitions 4
Subtopic: Atomic orbitals 1
Subtopic: Bond formation and bond breaking 5
Subtopic: Bond properties 4
Subtopic: Condensed formula 2
Subtopic: Constitutional isomers 3
Subtopic: Curved arrow notation 3
Subtopic: Dipole moments 3
Subtopic: Drawing and interpretation 5
Subtopic: Factors affecting acid strength 6
Subtopic: Formal charges 9
Subtopic: Hybridization 2
Subtopic: Octet rule exceptions 1
Subtopic: Periodic table trends 2
Subtopic: pKa 1
Subtopic: Polarity of molecules 3
Subtopic: Predicting acid/base reaction equilibrium 3
Subtopic: Resonance 6
Subtopic: Skeletal/bond-line structures 10
Subtopic: Types of bonds 4
Subtopic: VSEPR theory 5
Topic: Acids and Bases 10
Topic: Curved Arrows 6
Topic: Drawing Organic Molecules 13
Topic: Molecular Shape 10
Topic: Structure and Bonding 21