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TEST BANK for Organic Chemistry 6th Edition
Smith / All Chapters 1 - 29 / Full Complete
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Chapter 1 Structure and Bonding Chapter 2
Acids and Bases
Chapter 3 Introduction to Organic Molecules and Functional Groups Chapter 4
Alkanes
Chapter 5 Stereochemistry
Chapter 6 Understanding Organic Reactions
Chapter 7 Alkyl Halides and Nucleophilic Substitution
Chapter 8 Alkyl Halides and Elimination Reactions Chapter 9
Alcohols, Ethers, and Related Compounds Chapter 10
Alkenes and Addition Reactions
Chapter 11 Alkynes and Synthesis Chapter
12 Oxidation and Reduction Spectroscopy
A Mass Spectrometry Spectroscopy B
Infrared Spectroscopy
Spectroscopy C Nuclear Magnetic Resonance Spectroscopy Chapter 13
Radical Reactions
Chapter 14 Conjugation, Resonance, and Dienes Chapter 15
Benzene and Aromatic Compounds Chapter 16 Reactions of
Aromatic Compounds
Chapter 17 Introduction to Carbonyl Chemistry: Organometallic Reagents; Oxidation
and Reduction
Chapter 18 Aldehydes and Ketones—Nucleophilic Addition Chapter 19
Carboxylic Acids and Nitriles
Chapter 20 Carboxylic Acids and Their Derivatives- Nucleophilic Acyl Substitution
Chapter 21 Substitution Reactions of Carbonyl Compounds at the α-Carbon Chapter
22 Carbonyl Condensation Reactions
Chapter 23 Amines
Chapter 24 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis Chapter 25
Pericyclic Reactions
Chapter 26 Carbohydrates
Chapter 27 Amino Acids and Proteins
Chapter 28 Synthetic Polymers Chapter 29
Lipids (Available online)
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Chapter 1: Structure and Bonding
1. What is the ground-state electronic configuration of a carbon atom? A)
1s2
, 2s2
, 2p5
B) 1s2
, 2s2
, 2p2
C) 1s2
, 2s2
, 2p6
D) 1s2
, 2s2
, 2p4
2. What is the ground-state electronic configuration of a fluorine atom?
A) 1s2
, 2s2
, 2p2
B) 1s2
, 2s2
, 2p3
C) 1s2
, 2s2
, 2p4
D) 1s2
, 2s2
, 2p5
3. What is the ground-state electronic configuration of a magnesium cation (Mg2+
)?
A) 1s2
, 2s2
, 2p6
C) 1s2
, 2s2
, 2p6
, 3s2
B) 1s2
, 2s2
, 2p6
, 3s1
D) 1s2
, 2s2
, 2p6
, 3s2
, 3p2
4. What is the ground-state electronic configuration of a chlorine anion (Cl—
)?
A) 1s2
, 2s2
, 2p6
C) 1s2
, 2s2
, 2p6
, 3s2
, 3p5
B) 1s2
, 2s2
, 2p6
, 3s2
, 3p6
D) 1s2
, 2s2
, 2p6
, 3s2
, 3p4
5. Which of the following statements about valence electrons is true?
A) They are the most tightly held electrons.
B) They do not participate in chemical reactions.
Page 4
Chapter 1: Structure and Bonding
C) They are the outermost electrons.
D) They reveal the period number of a second-row element.
6. Which of the following statements about bonding is true?
A) Covalent bonds result from the transfer of electrons from one element to another.
B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.
C) Ionic bonds result from the sharing of electrons between two non-metals.
D) Covalent bonds result from the sharing of electrons between two metals.
7. Which of the following would you expect to have ionic bonds?
A) CO B) FBr C) NF3 D) NaCl
8. Which of the following molecules has nonpolar covalent bonds?
A) HCl B) N2 C) CHCl3 D) NO
9. Which of the following molecules contain both covalent and ionic bonds?
A) I, II B) I, IV C) II, III D) II, IV
10. Arrange the following bonds in decreasing order of ionic character, putting the most
ionic first.
A) I > II > III > IV C) IV > III > II > I
B) IV > II > I > III D) IV > II > III > I
11. Which of the following statements correctly describes the typical number of bonds for
carbon, nitrogen, and oxygen in most neutral organic molecules?
A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds and oxygen forms 3
covalent bonds.
B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms 2
covalent bonds.
Page 5
Chapter 1: Structure and Bonding
C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 2
covalent bonds.
D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 4
covalent bonds.
12. Which is not an acceptable Lewis structure for the anion CH2NCO—
?
A) I B) II C) III D) IV
13. Which of the following Lewis structures is correct?
A) I B) II C) III D) IV
14. Which of the following Lewis structures is correct?
A) I, II B) I, III C) II, III D) III, IV
15. Which is the correct Lewis structure for acetic acid (CH3CO2H)?
A) I B) II C) III D) IV
Page 6
Chapter 1: Structure and Bonding
16. In which of the following ions does carbon have a formal charge?
A) I B) II C) III D) None of the above
17. In which of the following ions does carbon have a formal charge?
A) I B) II C) III D) None of the above
18. What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple
bond?
A) 0 B) -2 C) -1 D) +1
19. Which of the following statements about constitutional isomers is true?
A) Constitutional isomers are different molecules having different molecular formula.
B) Constitutional isomers are different molecules having same molecular formula.
C) Constitutional isomers are same molecules having different molecular formula.
D) Constitutional isomers are same molecules having the same molecular formula.
20. How many constitutional isomers are there for a molecule having the molecular formula
C2H6O?
A) 1 B) 2 C) 3 D) 4
21. How many constitutional isomers are there for a molecule having the molecular C3H8O?
A) 1 B) 2 C) 3 D) 4
22. How many constitutional isomers are there for a molecule having the molecular formula
C3H6?
A) 1 B) 2 C) 3 D) 4
23. How many constitutional isomers are there for a molecule having the molecular formula
C2H4Cl2?
A) 1 B) 2 C) 3 D) 4
24. How many different isomers are there for a compound having the molecular formula
C3H6O?
A) 4 B) 5 C) 6 D) 7
Page 7
Chapter 1: Structure and Bonding
25. Which of the following molecules are constitutional isomers?
A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III
26. Which of the following compounds has an atom with an unfilled valence shell of
electrons?
A) H2O B) BCl3 C) CH4 D) CO2
27. Which of the following statements about resonance structures is true?
A) Resonance structures have the same placement of electrons but different
arrangement of atoms.
B) Resonance structures have the same placement of atoms but different arrangement
of electrons.
C) Resonance structures have the same placement of atoms and the same arrangement
of electrons.
D) Resonance structures have different placement of atoms and different arrangement
of electrons.
28. Which of the following statements about resonance structures is not true?
A) There is no movement of electrons from one form to another.
B) Resonance structures are not isomers.
C) Resonance structures differ only in the arrangement of electrons.
D) Resonance structures are in equilibrium with each other.
29. Which of the following pair does not represent resonance structures?
A) I B) II C) III D) IV
Page 8
Chapter 1: Structure and Bonding
30. What 2 things will change between two resonance structures?
A) The position of multiple bonds and non-bonded electrons.
B) The position of multiple bonds and single bonds.
C) The placement of atoms and single bonds.
D) The placement of atoms and non-bonded electrons.
31. Which of the following is a resonance structure of the compound below?
A) I B) II C) III D) IV
32. Which of the following resonance structures is the least important contributor to the
resonance hybrid of the formate anion, HCOO—
?
A) I B) II C) III D) IV
33. Rank the following in order of decreasing importance as contributing structures to the
resonance hybrid of formaldehyde, H2CO.
A) I > II > III B) I > III > II C) II > I > III D) III > II > I
Page 9
Chapter 1: Structure and Bonding
34. Follow the curved arrows to draw the second resonance structure for the ion below.
A) I B) II C) III D) IV
35. Which is more important in each pair of contributing resonance structures?
A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V
36. What is the approximate value of the H-C-H bond angle in methane, CH4?
A) 90° B) 109.5° C) 120° D) 180°
37. What is the approximate C-C-C bond angle in propene, CH3CH=CH2?
A) 90° B) 109.5° C) 120° D) 180°
38. What is the approximate H-C-O bond angle in formaldehyde, H2CO?
A) 90° B) 109.5° C) 120° D) 180°
Page 10
Chapter 1: Structure and Bonding
39. Determine the electron geometry around the indicated atom in each species.
A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral
B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear
C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar
D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral
40. What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN?
A) 90° B) 109.5° C) 120° D) 180°
41. Which of the following is the appropriate conversion of the condensed structure,
CH3COCH3, to a Lewis structure?
A) I B) II C) III D) IV
42. Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a
skeletal structure?
A) I B) II C) III D) IV
Page 11
Chapter 1: Structure and Bonding
43. Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?
A) I B) II C) III D) IV
44. What is the condensed formula of the compound below?
A) I B) II C) III D) IV
45. Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a
skeletal structure?
A) I B) II C) III D) IV
Page 12
Chapter 1: Structure and Bonding
46. Convert the following skeletal structure to a condensed structure.
A) I B) II C) III D) IV
47. Avobenzone is an active ingredient in some common sunscreens. Which of the
following is the correct molecular formula for avobenzone?
A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3
48. In which structure is the hybridization incorrect?
A) I B) II C) III D) IV
49. What is the hybridization for each of the indicated atoms in the following compound?
A) I = sp2
; II = sp2
; III = sp2
. C) I = sp; II = sp2
; III = sp3
.
Page 13
Chapter 1: Structure and Bonding
3
4
B) I = sp2
; II = sp3
; III = sp3
. D) I = sp2
; II = sp2
; III = sp3
.
50. What is the hybridization of the carbon atom in the methyl cation, (CH +
)?
A) sp3
B) sp2
C) sp D) p
51. What is the hybridization of the nitrogen atom in the ammonium cation, NH +
?
A) sp3
B) sp2
C) sp D) p
52. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of ethane,
CH3CH3?
A) Csp2
+ H1s B) Csp3
+ H1s C) C2p + H1s D) Csp + H1s
53. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of
ethylene, H2C=CH2?
A) C2p + H1s B) Csp + H1s C) Csp3
+ H1s D) Csp2
+ H1s
54. Which atomic orbitals overlap to form the carbon-carbon and bonding
molecular orbitals of ethylene, H2C=CH2?
A) Csp3
+ Csp3
, and C2p + C2p C) Csp2
+ Csp2
, and C2p + C2p
B) Csp3
+ Csp3
, and Csp2
+ Csp2
D) Csp2
+ Csp2
, and Csp2
+ Csp2
55. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of
acetylene, C2H2?
A) Csp + H1s B) C2p +H1s C) Csp3
+ H1s D) Csp2
+ H1s
56. Which atomic orbitals overlap to form the carbon-carbon bonding molecular orbital of
acetylene, C2H2?
A) Csp2
+ Csp2
B) Csp + Csp C) Csp3
+ Csp3
D) C2p + C2p
57. When forming molecular orbitals from atomic orbitals, what is the order of increasing
C-H bond strength for the following.
A) II < I < III B) III < I < II C) III < II < I D) I < II < III
58. What is the order of decreasing bond length for a C-C bond comprised of the following
molecular orbitals?
A) I > III > II B) I > II > III C) III > II > I D) II > III > I
Page 14
Chapter 1: Structure and Bonding
59. Which of the following statements about electronegativity and the periodic table is true?
A) Electronegativity decreases across a row of the periodic table.
B) Electronegativity increases down a column of the periodic table.
C) Electronegativity increases across a row of the periodic table.
D) Electronegativity does not change down a column of the periodic table.
60. Rank the following atoms in order of increasing electronegativity, putting the least
electronegative first.
A) I < II < III < IV C) III < II < IV < I
B) I < IV < II < III D) I < II < IV < III
61. Rank the following atoms in order of decreasing electronegativity, putting the most
electronegative first.
A) I > IV > II > III C) III > IV > II > I
B) II > III > IV > I D) III > II > IV > I
62. Which molecule has the greatest difference in electronegativity ( E) between the two
different elements?
A) CO2 B) H2S C) NH3 D) H2O
63. Which compound contains the most polar bond?
A) I B) II C) III D) IV
64. Which of the following compounds are non-polar?
A) I, IV B) I, II C) II, III D) II, IV
Page 15
Chapter 1: Structure and Bonding
65. Which of the following molecules has non-polar covalent bonds?
A) CO2 B) N2 C) CCl4 D) HF
66. Which of the following molecules has polar covalent bonds?
A) MgO B) NH3 C) Cl2 D) NaBr
67. Which of the following covalent bonds has the largest dipole moment?
A) C-H B) C-C C) C-O D) H-F
68. Which of the following molecules has the smallest dipole moment?
A) CO2 B) HCl C) H2O D) NH3
69. Which of the following molecules does not have a net dipole moment of zero?
A) CCl4 B) BF3 C) CO2 D) NH3
70. Which of the following molecules has a net dipole moment of zero?
A) I B) II C) III D) IV
Chapter 2: Acids and Bases
1. Which of the following statements is a correct definition for a Brønsted-Lowry acid?
A) Proton acceptor C) Electron pair acceptor
B) Electron pair donor D) Proton donor
2. Which of the following statements about a Brønsted-Lowry base is true?
A) The net charge may be zero, positive, or negative.
B) All Brønsted-Lowry bases contain a lone pair of electrons or a bond.
C) All Brønsted-Lowry bases contain a proton.
D) The net charge may be zero or positive.
Page 16
Chapter 1: Structure and Bonding
3 4
4
2 3
3. Which of the following compounds is both a Brønsted-Lowry acid and base?
A) I, II B) I, III C) II, IV D) I, IV
4. Which of the following species cannot act as both a Brønsted-Lowry acid and base?
A) HCO
-
B) HSO4
-
C) HO
-
D) H2PO -
5. Which of the following species is not a Brønsted-Lowry base?
A) BF3 B) NH3 C) H2O D) PO 3-
6. Which of the following statements about Brønsted-Lowry acids and bases is true?
A) Loss of a proton from a base forms its conjugate acid.
B) Loss of a proton from an acid forms its conjugate base.
C) Gain of a proton by an acid forms its conjugate base.
D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a
base to an acid.
7. Which of the following species is the conjugate base of methanol, CH3OH?
A) CH3OH
+
B) CH3O
-
C) CH -
D) CH4
8. Which of the following species is the conjugate base of the hydronium ion, H3O+
?
A) H3O B) H2O-
C) H2O D) HO-
9. Which of the following species is the conjugate acid of ammonia, NH3?
A) H4N B) H3N+
C) H2N-
D) H4N+
10. Which is the conjugate acid in the following reaction?
A) I B) II C) III D) IV
11. Which is the conjugate base in the following reaction?
A) I B) II C) III D) IV
Page 17
Chapter 1: Structure and Bonding
12. Which is the conjugate acid in the following reaction?
A) I B) II C) III D) IV
13. Which is the conjugate base in the following reaction?
A) I B) II C) III D) IV
14. Which of the following statements about acid strength is true?
A) The stronger the acid, the further the equilibrium lies to the left.
B) The stronger the acid, the smaller the Ka.
C) The stronger the acid, the larger the pKa.
D) The stronger the acid, the smaller the pKa.
15. Which of the following compounds is the strongest acid?
A) I B) II C) III D) IV
16. Which of the following compounds is the strongest acid?
A) CH3OH B) BrCH2OH C) CH3NH2 D) CH3Cl
17. Which of the following compounds is the weakest acid?
A) HF B) HCl C) HBr D) HI
18. Which of the following compounds is the weakest acid?
A) H2S B) PH3 C) HCl D) SiH4
19. Which of the following species is the strongest base?
A) HO-
B) H2N-
C) CH3COO-
D) Cl-
20. Which of the following ranks the compounds in order of increasing basicity, putting the
least basic first?
A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
Page 18
Chapter 1: Structure and Bonding
B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2
21. Consider the following molecule with protons labeled, I-III. Rank these protons in
order of decreasing acidity, putting the most acidic first.
A) I > II > III B) I > III > II C) III > II > I D) III > I > II
22. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
A) III < I < IV < II C) II < I < IV < III
B) III < IV < I < II D) III < I < II < IV
23. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
A) I < IV < III < II C) II < III < IV < I
B) I < III < IV < II D) II < IV < III < I
24. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
A) IV > II > III > I C) I > II > IV > III
Page 19
Chapter 1: Structure and Bonding
B) III > II > IV > I D) III > IV > II > I
25. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
A) IV > II > III > I C) III > IV > II > I
B) IV > III > II > I D) III > IV > I > II
26. Rank the following conjugate bases in order of increasing basicity, putting the least
basic first.
A) II < I < III B) II < III < I C) I < II < III D) I < III < II
27. Rank the following conjugate bases in order of decreasing basicity, putting the most
basic first.
A) II > I > III B) I > II > III C) III > I > II D) III > II > I
28. Which of the following is the strongest base?
A) CH3COCH3 B) CH3COOH C) NH3 D) H2O
29. What is the direction of equilibrium when acetylene (C2H2) reacts with H2N-
in an acid-
base reaction?
A) Left B) Right C) Neither D) Cannot be determined
Page 20
Chapter 1: Structure and Bonding
3
30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide
(CH3CH2O-
) in an acid-base reaction?
A) Left B) Right C) Neither D) Cannot be determined
31. Which of the following statements explain why H2O is a stronger acid than CH4?
A) H2O can form hydrogen bonds while CH4 cannot.
B) H2O forms a less stable conjugate base, HO-
.
C) CH4 forms a more stable conjugate base, CH -
.
D) H2O forms a more stable conjugate base, HO-
.
32. Which of the following statements explain why HBr is a stronger acid than HF?
A) Br-
is more stable than F-
because Br-
is larger than F-
.
B) Br-
is less stable than F-
because Br-
is larger than F-
.
C) Br-
is more stable than F-
because Br-
is less electronegative than F-
.
D) Br-
is less stable than F-
because Br-
is less electronegative than F-
.
33. Which of the following compounds has the lowest pKa?
A) H2O B) H2S C) NH3 D) CH4
34. Which of the following concepts can be used to explain the difference in acidity
between acetic acid (CH3COOH) and ethanol (CH3CH2OH)?
A) Hybridization B) Electronegativity C) Resonance D) Size
35. Which of the following concepts can be used to explain the difference in acidity
between acetylene (C2H2) and ethylene (C2H4)?
A) Size B) Resonance C) Inductive effect D) Hybridization
36. Which of the following concepts can be used to explain the difference in acidity
between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)?
A) Size B) Inductive effect C) Resonance D) Hybridization
Page 21
Chapter 1: Structure and Bonding
37. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
38. Which of the following statements about Lewis acids is true?
A) Lewis acids are proton donors.
B) Lewis acids are proton acceptors.
C) Lewis acids are electron pair donors.
D) Lewis acids are electron pair acceptors.
39. Which of the following statements about Lewis bases is true?
A) Lewis bases are electron pair acceptors.
B) Lewis bases are electron pair donors.
C) Lewis bases are proton donors.
D) Lewis bases are proton acceptors.
40. Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH3OH B) H2O C) CH3COOH D) BF3
41. Which of the following species can be both Lewis acid and Lewis base?
A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III
42. What is the correct classification of the following compound?
CH3-O-CH3
A) Brønsted-Lowry acid and Lewis acid. C) Brønsted-Lowry base.
B) Brønsted-Lowry base and Lewis base. D) Lewis base.
Page 22
Chapter 1: Structure and Bonding
43. Identify the Lewis acid in the following reaction.
A) I B) II C) III D) IV
44. Identify the Lewis base in the following reaction.
A) I B) II C) III D) IV
45. Which of the following compounds is not a Lewis acid?
A) AlCl3 B) HCl C) H2O D) CBr4
46. What is the role of methylchloride (CH3Cl) in the following reaction?
A) Lewis acid C) Brønsted-Lowry acid
B) Lewis base D) Brønsted-Lowry base
47. What is the electrophilic site in the following compounds?
A) I = Carbon; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron.
B) I = Chlorine; II = carbon; III = boron. D) I = Carbon; II = carbon; III = fluorine.
48. What is the nucleophilic site in the following compounds?
A) I = Hydrogen; II = electrons in bond; III = nitrogen.
B) I = Oxygen; II = carbon; III = nitrogen.
C) I = Hydrogen; II = carbon; III = carbon.
Page 23
Chapter 1: Structure and Bonding
D) I = Oxygen; II = electrons in bond; III = nitrogen.
Chapter 3: Intro. to Organic Molecules & Functional Groups
1. Which of the following lists contains common heteroatoms found in organic molecules?
A) N, O, S, P, Cl C) Na, Mg, S, N, Cl
B) Na, O, S, P, Cl D) Na, Mg, O, N, Cl
2. Why do heteroatoms confer reactivity on a particular molecule?
A) Because they have lone pairs and create electron-rich sites on carbon.
B) Because they have lone pairs and create electron-deficient sites on carbon.
C) Because they are electronegative and act as electrophiles.
D) Because they are electropositive and act as nucleophiles.
3. Why do bonds confer reactivity on a particular molecule?
A) Because bonds are difficult to break in chemical reactions.
B) Because bonds make a molecule an acid.
C) Because bonds are easily broken in chemical reactions.
D) Because bonds make a molecule an electrophile.
4. Which of the following molecules contain the same functional groups?
A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV
5. Which of the following molecules contain the same functional groups?
A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV
Page 24
Chapter 1: Structure and Bonding
6. Which of the following molecules are aliphatic hydrocarbons?
A) I, II, III B) I and III C) II, III, IV D) II and IV
7. Which of the following molecules are aromatic hydrocarbons?
A) I B) II C) III D) I and III
8. Which of the following correctly matches the molecules to the names of the functional
groups?
I. CH3OH Carboxylic acid
II. CH3CO2CH3 Ester
III. CH3COCH3 Ketone
IV. H2CO Alcohol
A) I and II B) III and IV C) II and III D) II and IV
9. Which of the following correctly matches the molecules to the names of the functional
groups?
I. CH3OCH3 Ether
II. CH3CONH2 Amine
III. CH3SH Thiol
IV. CH3CHO Alcohol
A) I and II B) II and III C) III and IV D) I and III
10. Which of the following correctly matches the molecules to the names of the functional
groups?
I. CH3NH2 Amide
II. CH3SCH3 Sulfide
III. CH3CONH2 Amine
IV. CH3CO2CH3 Ester
A) I and II B) II and IV C) III and IV D) II and III
Page 25
Chapter 1: Structure and Bonding
11. Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the
following lists the correct functional groups present in donepezil?
A) Amide, aromatic, ether, ketone. C) Amine, aromatic, ester, ketone.
B) Amide, aromatic, ester, ketone. D) Amine, aromatic, ether, ketone.
12. Consider the molecule atenolol (a blocker used to treat hypertension). Which of the
following lists the correct functional groups present in atenolol?
A) Primary alcohol, amide, primary amine, aromatic, ether.
B) Secondary alcohol, amide, secondary amine, aromatic, ether.
C) Secondary alcohol, amide, primary amine, aromatic, ether.
D) Secondary alcohol, amide, secondary amine, aromatic, ester.
13. Which of the following structures contains a secondary amine?
A) I B) II C) III D) IV
14. Which of the following structures contains a primary amine?
A) I B) II C) III D) IV
Page 26
Chapter 1: Structure and Bonding
15. Which of the following structures contains an amide?
A) I B) II C) III D) IV
16. Which of the following structures contains an alkene?
A) I B) II C) III D) IV
17. Which of the following is a tertiary amine?
A) I B) II C) III D) IV
18. Which of the following is a secondary alcohol?
A) I B) II C) III D) IV
19. Which of the following statements best describes the relationship between the surface
area of a molecule and the strength of the intermolecular forces?
A) The larger the surface area, the weaker the intermolecular force.
B) The larger the surface area, the stronger the intermolecular forces.
C) The smaller the surface area, the stronger the intermolecular forces.
D) There is no relationship between surface area and intermolecular forces.
Page 27
Chapter 1: Structure and Bonding
20. Rank the following compounds in order of increasing strength of intermolecular forces,
putting the molecule with the weakest intermolecular force first.
A) I < II < III B) II < I < III C) I < III < II D) II < III < I
21. Which of the following compounds has the lowest boiling point?
A) I B) II C) III D) IV
22. Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
23. Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
24. Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
Page 28
Chapter 1: Structure and Bonding
25. Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
26. Rank the following compounds in order of decreasing boiling point, putting the
compound with the highest boiling point first.
A) I > II > III > IV C) III > II > IV > I
B) III > IV > II > I D) I > IV > II > III
27. Which of the following compounds can form intermolecular hydrogen bonds with a
molecule similar to itself?
A) I B) II C) III D) IV
28. What is the strongest intermolecular force present in 1-propanol?
A) Ion-ion C) Dipole-dipole
B) Hydrogen bonding D) Induced dipole-induced dipole
29. What intermolecular force is generally considered the strongest?
A) Hydrogen bonding C) Covalent bonds
B) London dispersion forces D) Dipole-dipole
30. What intermolecular force is generally considered the weakest?
A) Hydrogen bonding C) Dipole-dipole
B) London dispersion forces D) Ion-ion
Page 29
Chapter 1: Structure and Bonding
31. Rank the following compounds in order of increasing melting point, putting the
compound with the least melting point first.
A) II < I < III B) I < III < II C) I < II < III D) III < II < I
32. Rank the following compounds in order of decreasing melting point, putting the
compound with the highest melting point first.
A) I > II > III B) II > III > I C) III > II > I D) III > I > II
33. Which of the following intermolecular forces would not form between similar
molecules of the structure below?
A) London dispersion forces C) Hydrogen bonding
B) Ion-ion D) Dipole-dipole
34. Which of the following alkanes is expected to have the highest melting point?
A) I B) II C) III D) IV
35. Which of the following compounds is expected to be the least soluble in H2O?
A) I B) II C) III D) IV
Page 30
Chapter 1: Structure and Bonding
36. Which of the following compounds is expected to be the most soluble in H2O?
A) I B) II C) III D) IV
37. Which of the following compounds would be expected to be more soluble in hexane
(C6H14)?
A) I B) II C) III D) IV
38. Which of the following statements about the solubility of organic compounds in H2O is
true?
A) The non-polar part of a molecule that is not attracted to water is said to be
hydrophilic.
B) The non-polar part of a molecule that is not attracted to water is said to be
hydrophobic.
C) The polar part of a molecule that can hydrogen bond to water is said to be
hydrophobic.
D) For an organic compound with one functional group that contains an O or N atom,
the compound is water soluble only if it has 5 carbons.
39. Which of the following compounds is expected to be H2O soluble?
A) I B) II C) III D) IV
40. What molecular features are required for soap to properly dissolve grease and oil?
A) The molecule must be large.
B) The molecule must contain a polar head.
C) The molecule must contain a non-polar tail.
D) B and C are required.
Page 31
Chapter 1: Structure and Bonding
41. Which of the following statements about vitamin A, drawn below, are true?
A) Vitamin A is soluble in H2O.
B) Vitamin A is insoluble in organic solvents.
C) Vitamin A contains an aromatic ring.
D) Vitamin A is insoluble in H2O.
42. Which of the following statements about vitamin C, drawn below, are true?
A) Vitamin C is insoluble in H2O.
B) Vitamin C is soluble in H2O.
C) Vitamin C is an aliphatic hydrocarbon.
D) Vitamin C contains a ketone functional group.
43. Which of the following could most likely serve as an ionophore?
A) I B) II C) III D) IV
Page 32
Chapter 1: Structure and Bonding
44. The indicated carbon atom is:
A) Electrophilic because it is electron-deficient.
B) Nucleophilic because it is electron-deficient.
C) Electrophilic because it is electron-rich.
D) Nucleophilic because it is electron-rich.
45. The indicated bond is:
A) Nucleophilic because it is electron-deficient.
B) Electrophilic because it is electron-deficient.
C) Nucleophilic because it electron-rich.
D) Electrophilic because it is electron-rich.
46. The indicated bond is:
A) Nucleophilic because it is electron-deficient.
B) Electrophilic because it is electron-rich.
C) Nucleophilic because it is electron-rich.
D) Electrophilic because it is electron-deficient.
Page 33
Chapter 1: Structure and Bonding
47. Which of the following list the correct functional groups found in aspartame, the
artificial sweetener?
A) Amine, aromatic, carboxylic acid, ether, ketone.
B) Amine, amide, aromatic, carboxylic acid, ester.
C) Amide, alcohol, aromatic, carboxylic acid, ether.
D) Amine, aromatic, carboxylic acid, ester, nitrile.
48. Rank the following compounds in order of decreasing boiling point, putting the
compound with the highest boiling point first.
A) I > III > IV > II C) IV > I > II > III
B) IV > II > I > III D) I > IV > II > III
Chapter 4: Alkanes
1. Which of the following statements about alkanes is not true?
A) Alkanes are aliphatic hydrocarbons.
B) Alkanes contain only C-C and C-H bonds.
C) Alkanes are acyclic or cyclic.
D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of
carbons.
2. Which of the following statements about alkanes is true?
A) Alkanes are aliphatic hydrocarbons having only C-C and C-H bonds.
Page 34
Chapter 1: Structure and Bonding
B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of
carbons.
C) Acyclic alkanes contain carbons joined in one or more rings.
D) Acyclic alkanes have general molecular formula CnH2n.
3. What is the molecular formula of an alkane that has twenty-three carbon atoms?
A) C23H46 B) C23H48 C) C23H50 D) C23H44
4. What is the molecular formula of a cycloalkane that has six carbon atoms?
A) C6H14 B) C6H10 C) C6H12 D) C6H16
5. What is the approximate C-C-C bond angle in propane?
A) 90° B) 109.5° C) 120° D) 180°
6. What is the hybridization of a carbon atom in an alkane?
A) sp3
B) sp2
C) sp D) p
7. How many constitutional isomers are there with the molecular formula C5H12?
A) 2 B) 3 C) 4 D) 5
8. How many constitutional isomers are there with the molecular formula C6H14?
A) 2 B) 3 C) 4 D) 5
9. Which of the following is not another representation for 2-methylbutane?
A) I B) II C) III D) IV
10. Which of the following compounds has primary, secondary, tertiary and quaternary
carbon atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
11. Which of the following compounds has only primary and secondary carbon atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,3,3-Trimethylpentane
Page 35
Chapter 1: Structure and Bonding
12. Which of the following compounds has only primary, secondary and tertiary carbon
atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
13. Which of the following compounds has only primary, secondary and quaternary carbon
atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
14. Which of the following compounds has primary, secondary and tertiary hydrogen
atoms?
A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane
15. Which of the following compounds has only primary and secondary hydrogen atoms?
A) 2-Methylpentane C) 3-Methylpentane
B) 2,2,3-Trimethylpentane D) 2,2-Dimethylpentane
16. How many cycloalkane constitutional isomers (excluding stereoisomers) are there with
molecular formula C5H10?
A) 2 B) 3 C) 4 D) 5
17. What is the parent chain for the following compound?
A) Hexane B) Heptane C) Octane D) Nonane
18. What is the parent chain for the following compound?
A) Heptane B) Octane C) Nonane D) Decane
19. What is the name of the alkyl group that contains two carbons in a straight chain and
one-carbon branch?
A) Ethyl B) Propyl C) Isopropyl D) None of the above
Page 36
Chapter 1: Structure and Bonding
20. What is the IUPAC name for the following compound?
A) 4-Ethyl-5-methyloctane C) 4-Methyl-3-propylheptane
B) 4-Methyl-5-ethyloctane D) 4-Methyl-5-propyloctane
21. What is the IUPAC name for the following compound?
A) 3,5-Diethyl-6-methylheptane C) 3-Ethyl-5-isopropylheptane
B) 3,5-Diethyl-2-methylheptane D) 5-Ethyl-3-isopropylheptane
22. What is the IUPAC name for the following compound?
A) 2,3-Dimethyl-4-sec-butylheptane C) 3,5,6-Trimethyl-4-propylheptane
B) 4-sec-Butyl-2,3-dimethylheptane D) 2,3,5-Trimethyl-4-propylheptane
23. What is the IUPAC name for the following compound?
A) 5-Ethyl-3,6-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane
B) 3-Ethyl-2,5-dimethylheptane D) 5-Ethyl-3,6-dimethyloctane
Page 37
Chapter 1: Structure and Bonding
24. What is the IUPAC name for the following compound?
A) 2,3,5-Trimethylhexane C) 2,4-Diethyl-5-methylheptane
B) 2,4,5-Triethylhexane D) 4-Ethyl-3,6-dimethyloctane
25. What is the IUPAC name for the following compound?
A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane
B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane
C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane
D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane
26. What is the IUPAC name for the following compound?
A) 3-Ethyl-1-methylcyclohexane C) 1-Ethyl-3-methylhexane
B) 1-Ethyl-3-methylcyclohexane D) 3-Ethyl-1-methylhexane
27. What is the IUPAC name for the following compound?
A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane
B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane
C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane
Page 38
Chapter 1: Structure and Bonding
D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane
28. What is the IUPAC name for the following compound?
A) 1,4-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane
B) 1,3-Dimethylcyclohexane D) 1,4-Dimethylcyclopentane
29. What is the IUPAC name for the following compound?
A) 1-Butylcyclohexane C) 1-Cyclohexylbutane
B) Cyclohexanebutane D) Butylcyclohexane
30. What is the IUPAC name for the following compound?
A) Hexylcyclopentane C) 1-Cyclopentylhexane
B) 1-Hexylcyclopentane D) 1-Cyclopentylheptane
31. What is the IUPAC name for the following compound?
A) 1-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane
B) 1-sec-Butyl-3-methylcyclohexane D) 1-sec-Butyl-3-methylhexane
32. What is the common name of the following alkyl group?
A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl
Page 39
Chapter 1: Structure and Bonding
33. What is the common name of the following alkyl group?
A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl
34. Rank the following alkanes in order of decreasing boiling point, putting the alkane with
the highest boiling point first.
A) I > II > III B) I > III > II C) II > III > I D) III > II > I
35. Rank the following alkanes in order of increasing melting point, putting the alkane with
the lowest melting point first.
A) I < III < II B) I < II < III C) II < III < I D) III < II < I
36. Which of the following statements about the conformations of acyclic alkanes is true?
A) Conformations are the same arrangements of atoms that cannot be interconverted
by rotation about single bonds.
B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond
angle on the adjacent carbon.
C) In the staggered conformation, the C-H bonds on one carbon are directly aligned
with the C-H bonds on the adjacent carbon.
D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a
staggered conformation, and vice versa.
37. Which of the following statements about the conformations of acyclic alkanes is not
true?
A) The staggered and eclipsed conformations are equally stable.
B) The staggered conformations are more stable than the eclipsed conformations.
C) An energy minimum and maximum occur every 60° as the conformation changes
from staggered to eclipsed.
D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
Page 40
Chapter 1: Structure and Bonding
38. Which of the following statements about the conformations of acyclic alkanes is true?
A) A staggered conformation with two larger groups 180° from each other is called
gauche.
B) Staggered conformations are at energy maxima and eclipsed conformations are
energy minima.
C) A staggered conformation with two larger groups 60° from each other is called
anti.
D) Gauche conformations are generally higher in energy than anti conformations.
39. Which of the following is not a conformer of butane?
A) I B) II C) III D) IV
40. Which of the following are gauche conformers?
A) I and II B) I and III C) II and IV D) II and III
41. Which of the following are anti conformers?
A) I and II B) II and III C) I and IV D) II and IV
Page 41
Chapter 1: Structure and Bonding
42. Which of the following conformers has the highest energy?
A) I B) II C) III D) IV
43. Rank the conformers of butane in order of decreasing stability, putting the most stable
first.
A) IV > I > II > III C) II > III > I > IV
B) IV > I > III > II D) I > IV > II > III
44. Which of the following is the highest energy conformer of 2,3-dimethylbutane?
A) I B) II C) III D) IV
45. Which of the following is the lowest energy conformer of 2,3-dimethybutane?
A) I B) II C) III D) IV
Page 42
Chapter 1: Structure and Bonding
46. Which of the following cycloalkanes has the most angle strain?
A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
47. Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane
48. Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?
A) I B) II C) III D) IV
49. Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?
A) I B) II C) III D) IV
50. Which of the following is the most stable conformation of cis-1-ethyl-3-
isopropylcyclohexane?
A) I B) II C) III D) IV
51. Which of the following is the most stable conformation of trans-1-isopropyl-3-
methylcyclohexane?
A) I B) II C) III D) IV
Page 43
Chapter 1: Structure and Bonding
52. Select the most stable conformer of cis-1,3-cyclohexanediol.
A) I B) II C) III D) IV
53. What is the alternate chair conformation of the following compound?
A) I B) II C) III D) IV
54. Which of the following is the most stable conformation of the following compound?
A) I B) II C) III D) IV
Page 44
Chapter 1: Structure and Bonding
55. Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability,
putting the most stable first.
A) I > II > III > IV C) III > IV > II > I
B) III > II > IV > I D) I > II > IV > III
56. What are the products of the combustion of alkanes?
A) Carbon and hydrogen C) Carbon dioxide and hydrogen
B) Carbon and water D) Carbon dioxide and water
Chapter 5: Stereochemistry
1. What is the main carbohydrate in the seeds and roots of plants?
A) Starch B) Glucose C) Cellulose D) Glycogen
2. Which of the following statements about starch and cellulose is true?
A) Starch and cellulose are not stereoisomers.
B) In cellulose, the O atom joins two rings using one equatorial and one axial bond.
C) In starch, the O atom joins two rings using two equatorial bonds.
D) In cellulose, the O atom joins two rings using two equatorial bonds.
3. Which of the following statements about constitutional isomers if not true?
A) They have different IUPAC names.
B) They always have the same functional groups.
C) They have different physical properties.
D) They have different chemical properties.
Page 45
Chapter 1: Structure and Bonding
4. Which of the following statements about stereoisomers is not true?
A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans.
B) Stereoisomers differ in configuration.
C) Stereoisomers always have the same functional groups.
D) Stereoisomers differ only in their structural formula.
5. What is the relationship between the following two compounds?
A) Stereoisomers C) Identical
B) Constitutional isomers D) Not isomers, different compounds
6. What is the relationship between the following two compounds?
A) Constitutional isomers C) Stereoisomers
B) Identical D) Not isomers, different compounds
7. What is the relationship between the following two compounds?
A) Constitutional isomers C) Stereoisomers
B) Identical D) Not isomers, different compounds
8. What is the relationship between the following two compounds?
A) Constitutional isomers C) Identical
B) Stereoisomers D) Not isomers, different compounds
Page 46
Chapter 1: Structure and Bonding
9. Which of the following is the definition of chirality?
A) The existence of a molecule with a mirror image.
B) The existence of a molecule with a carbon atom that has four different substituents.
C) The existence of a molecule that is superimposable on its mirror image.
D) The existence of a molecule that is not superimposable on its mirror image.
10. Which of the following statements is not true?
A) A molecule that is superimposable on its mirror image is said to achiral.
B) A molecule that is not superimposable on its mirror image is said to be chiral.
C) A molecule that is superimposable on its mirror image is said to be chiral.
D) A carbon atom bonded to four different groups is a stereogenic center.
11. Which of the following statements is true?
A) Enantiomers are mirror images that are not superimposable.
B) A molecule that is superimposable on its mirror image is chiral.
C) A chiral molecule usually contains a plane of symmetry.
D) An achiral molecule does not contain a plane of symmetry.
12. Which of the following statements is true?
A) Achiral molecules usually contain a plane of symmetry.
B) With one tetrahedral stereogenic center, a molecule may or may not be chiral.
C) With two or more stereogenic centers, a molecule is always chiral.
D) Chiral molecules usually contain a plane of symmetry.
13. Which of the following is the correct definition for a pair of enantiomers?
A) A pair of stereoisomers that have a plane of symmetry.
B) A pair of stereoisomers that are not mirror images of each other.
C) A pair of stereoisomers that are not superimposable mirror images of each other.
D) A pair of stereoisomers that are superimposable mirror images of each other.
Page 47
Chapter 1: Structure and Bonding
14. Which of the following molecules has a plane of symmetry?
A) I B) II C) III D) IV
15. Which of the following statements is true?
A) The presence of a plane of symmetry makes a molecule chiral.
B) An achiral molecule must have one or more stereogenic centers.
C) All molecules that have stereogenic centers are chiral.
D) Stereoisomers that are not superimposable on their mirror image are enantiomers.
16. Which of the following molecules are chiral?
I. cis-1,3-Dibromocyclohexane
II. 1-Bromo-1-methylcyclohexane
III. trans-1-Bromo-3-methylcyclohexane
IV.cis-1-Bromo-3-methylcyclohexane
A) I, II B) II, III C) I, IV D) III, IV
17. Which of the following molecules are chiral?
I. 2-Chlorobutane
II. 3-Bromopentane
III. 1-Bromo-2-methylpropene
IV.2-Bromo-3-methylbutane
A) I, II B) I, IV C) II, III D) III, IV
18. Which of the following molecules are achiral?
A) II, III B) I, II C) I, IV D) III, IV
Page 48
Chapter 1: Structure and Bonding
19. Which of the following molecules are chiral?
A) II, III B) I, II C) I, IV D) III, IV
20. How many stereogenic centers are present in ephedrine, a bronchodilator and
decongestant?
A) 0 B) 1 C) 2 D) 3
21. How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
22. How many stereogenic centers are present in fructose, a simple sugar?
A) 1 B) 2 C) 3 D) 4
Page 49
Chapter 1: Structure and Bonding
23. How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
24. How many stereogenic centers are present in menthol?
A) 1 B) 2 C) 3 D) 4
25. How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
26. How many stereogenic centers are present in the following molecule?
A) 1 B) 2 C) 4 D) 5
27. How many stereoisomers are possible for a molecule with formula
CH3CHBrCH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
28. How many stereoisomers can be drawn for a molecule with formula
CH3CH(OH)CH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
Page 50
Chapter 1: Structure and Bonding
29. What is the total number of possible stereoisomers for the following molecule?
A) 2 B) 4 C) 6 D) 8
30. How many isomers can be drawn (constitutional and stereoisomers) for
dimethycyclopropane?
A) 2 B) 3 C) 4 D) 6
31. How many chiral stereoisomers can be drawn for dimethycyclopropane?
A) 1 B) 2 C) 3 D) 4
32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures
and certain types of chronic pain?
A) 0 B) 1 C) 2 D) 3
33. How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
A) III > I > II > IV C) III > II > IV > I
B) I > II > IV > III D) III > IV > II > I

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  • 1. TO GET ALL CHAPTERS EMAIL ME AT>>>>> donc8246@gmail.com Page 1 TEST BANK for Organic Chemistry 6th Edition Smith / All Chapters 1 - 29 / Full Complete
  • 2. Page 2 TO GET ALL CHAPTERS EMAIL ME AT>>>>> donc8246@gmail.com Chapter 1 Structure and Bonding Chapter 2 Acids and Bases Chapter 3 Introduction to Organic Molecules and Functional Groups Chapter 4 Alkanes Chapter 5 Stereochemistry Chapter 6 Understanding Organic Reactions Chapter 7 Alkyl Halides and Nucleophilic Substitution Chapter 8 Alkyl Halides and Elimination Reactions Chapter 9 Alcohols, Ethers, and Related Compounds Chapter 10 Alkenes and Addition Reactions Chapter 11 Alkynes and Synthesis Chapter 12 Oxidation and Reduction Spectroscopy A Mass Spectrometry Spectroscopy B Infrared Spectroscopy Spectroscopy C Nuclear Magnetic Resonance Spectroscopy Chapter 13 Radical Reactions Chapter 14 Conjugation, Resonance, and Dienes Chapter 15 Benzene and Aromatic Compounds Chapter 16 Reactions of Aromatic Compounds Chapter 17 Introduction to Carbonyl Chemistry: Organometallic Reagents; Oxidation and Reduction Chapter 18 Aldehydes and Ketones—Nucleophilic Addition Chapter 19 Carboxylic Acids and Nitriles Chapter 20 Carboxylic Acids and Their Derivatives- Nucleophilic Acyl Substitution Chapter 21 Substitution Reactions of Carbonyl Compounds at the α-Carbon Chapter 22 Carbonyl Condensation Reactions Chapter 23 Amines Chapter 24 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis Chapter 25 Pericyclic Reactions Chapter 26 Carbohydrates Chapter 27 Amino Acids and Proteins Chapter 28 Synthetic Polymers Chapter 29 Lipids (Available online)
  • 3. Page 3 TO GET ALL CHAPTERS EMAIL ME AT>>>>> donc8246@gmail.com Chapter 1: Structure and Bonding 1. What is the ground-state electronic configuration of a carbon atom? A) 1s2 , 2s2 , 2p5 B) 1s2 , 2s2 , 2p2 C) 1s2 , 2s2 , 2p6 D) 1s2 , 2s2 , 2p4 2. What is the ground-state electronic configuration of a fluorine atom? A) 1s2 , 2s2 , 2p2 B) 1s2 , 2s2 , 2p3 C) 1s2 , 2s2 , 2p4 D) 1s2 , 2s2 , 2p5 3. What is the ground-state electronic configuration of a magnesium cation (Mg2+ )? A) 1s2 , 2s2 , 2p6 C) 1s2 , 2s2 , 2p6 , 3s2 B) 1s2 , 2s2 , 2p6 , 3s1 D) 1s2 , 2s2 , 2p6 , 3s2 , 3p2 4. What is the ground-state electronic configuration of a chlorine anion (Cl— )? A) 1s2 , 2s2 , 2p6 C) 1s2 , 2s2 , 2p6 , 3s2 , 3p5 B) 1s2 , 2s2 , 2p6 , 3s2 , 3p6 D) 1s2 , 2s2 , 2p6 , 3s2 , 3p4 5. Which of the following statements about valence electrons is true? A) They are the most tightly held electrons. B) They do not participate in chemical reactions.
  • 4. Page 4 Chapter 1: Structure and Bonding C) They are the outermost electrons. D) They reveal the period number of a second-row element. 6. Which of the following statements about bonding is true? A) Covalent bonds result from the transfer of electrons from one element to another. B) Ionic bonds result from the transfer of electrons from a metal to a non-metal. C) Ionic bonds result from the sharing of electrons between two non-metals. D) Covalent bonds result from the sharing of electrons between two metals. 7. Which of the following would you expect to have ionic bonds? A) CO B) FBr C) NF3 D) NaCl 8. Which of the following molecules has nonpolar covalent bonds? A) HCl B) N2 C) CHCl3 D) NO 9. Which of the following molecules contain both covalent and ionic bonds? A) I, II B) I, IV C) II, III D) II, IV 10. Arrange the following bonds in decreasing order of ionic character, putting the most ionic first. A) I > II > III > IV C) IV > III > II > I B) IV > II > I > III D) IV > II > III > I 11. Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules? A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds and oxygen forms 3 covalent bonds. B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms 2 covalent bonds.
  • 5. Page 5 Chapter 1: Structure and Bonding C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 2 covalent bonds. D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 4 covalent bonds. 12. Which is not an acceptable Lewis structure for the anion CH2NCO— ? A) I B) II C) III D) IV 13. Which of the following Lewis structures is correct? A) I B) II C) III D) IV 14. Which of the following Lewis structures is correct? A) I, II B) I, III C) II, III D) III, IV 15. Which is the correct Lewis structure for acetic acid (CH3CO2H)? A) I B) II C) III D) IV
  • 6. Page 6 Chapter 1: Structure and Bonding 16. In which of the following ions does carbon have a formal charge? A) I B) II C) III D) None of the above 17. In which of the following ions does carbon have a formal charge? A) I B) II C) III D) None of the above 18. What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond? A) 0 B) -2 C) -1 D) +1 19. Which of the following statements about constitutional isomers is true? A) Constitutional isomers are different molecules having different molecular formula. B) Constitutional isomers are different molecules having same molecular formula. C) Constitutional isomers are same molecules having different molecular formula. D) Constitutional isomers are same molecules having the same molecular formula. 20. How many constitutional isomers are there for a molecule having the molecular formula C2H6O? A) 1 B) 2 C) 3 D) 4 21. How many constitutional isomers are there for a molecule having the molecular C3H8O? A) 1 B) 2 C) 3 D) 4 22. How many constitutional isomers are there for a molecule having the molecular formula C3H6? A) 1 B) 2 C) 3 D) 4 23. How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2? A) 1 B) 2 C) 3 D) 4 24. How many different isomers are there for a compound having the molecular formula C3H6O? A) 4 B) 5 C) 6 D) 7
  • 7. Page 7 Chapter 1: Structure and Bonding 25. Which of the following molecules are constitutional isomers? A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III 26. Which of the following compounds has an atom with an unfilled valence shell of electrons? A) H2O B) BCl3 C) CH4 D) CO2 27. Which of the following statements about resonance structures is true? A) Resonance structures have the same placement of electrons but different arrangement of atoms. B) Resonance structures have the same placement of atoms but different arrangement of electrons. C) Resonance structures have the same placement of atoms and the same arrangement of electrons. D) Resonance structures have different placement of atoms and different arrangement of electrons. 28. Which of the following statements about resonance structures is not true? A) There is no movement of electrons from one form to another. B) Resonance structures are not isomers. C) Resonance structures differ only in the arrangement of electrons. D) Resonance structures are in equilibrium with each other. 29. Which of the following pair does not represent resonance structures? A) I B) II C) III D) IV
  • 8. Page 8 Chapter 1: Structure and Bonding 30. What 2 things will change between two resonance structures? A) The position of multiple bonds and non-bonded electrons. B) The position of multiple bonds and single bonds. C) The placement of atoms and single bonds. D) The placement of atoms and non-bonded electrons. 31. Which of the following is a resonance structure of the compound below? A) I B) II C) III D) IV 32. Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO— ? A) I B) II C) III D) IV 33. Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO. A) I > II > III B) I > III > II C) II > I > III D) III > II > I
  • 9. Page 9 Chapter 1: Structure and Bonding 34. Follow the curved arrows to draw the second resonance structure for the ion below. A) I B) II C) III D) IV 35. Which is more important in each pair of contributing resonance structures? A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V 36. What is the approximate value of the H-C-H bond angle in methane, CH4? A) 90° B) 109.5° C) 120° D) 180° 37. What is the approximate C-C-C bond angle in propene, CH3CH=CH2? A) 90° B) 109.5° C) 120° D) 180° 38. What is the approximate H-C-O bond angle in formaldehyde, H2CO? A) 90° B) 109.5° C) 120° D) 180°
  • 10. Page 10 Chapter 1: Structure and Bonding 39. Determine the electron geometry around the indicated atom in each species. A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral 40. What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN? A) 90° B) 109.5° C) 120° D) 180° 41. Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure? A) I B) II C) III D) IV 42. Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a skeletal structure? A) I B) II C) III D) IV
  • 11. Page 11 Chapter 1: Structure and Bonding 43. Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure? A) I B) II C) III D) IV 44. What is the condensed formula of the compound below? A) I B) II C) III D) IV 45. Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure? A) I B) II C) III D) IV
  • 12. Page 12 Chapter 1: Structure and Bonding 46. Convert the following skeletal structure to a condensed structure. A) I B) II C) III D) IV 47. Avobenzone is an active ingredient in some common sunscreens. Which of the following is the correct molecular formula for avobenzone? A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3 48. In which structure is the hybridization incorrect? A) I B) II C) III D) IV 49. What is the hybridization for each of the indicated atoms in the following compound? A) I = sp2 ; II = sp2 ; III = sp2 . C) I = sp; II = sp2 ; III = sp3 .
  • 13. Page 13 Chapter 1: Structure and Bonding 3 4 B) I = sp2 ; II = sp3 ; III = sp3 . D) I = sp2 ; II = sp2 ; III = sp3 . 50. What is the hybridization of the carbon atom in the methyl cation, (CH + )? A) sp3 B) sp2 C) sp D) p 51. What is the hybridization of the nitrogen atom in the ammonium cation, NH + ? A) sp3 B) sp2 C) sp D) p 52. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of ethane, CH3CH3? A) Csp2 + H1s B) Csp3 + H1s C) C2p + H1s D) Csp + H1s 53. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of ethylene, H2C=CH2? A) C2p + H1s B) Csp + H1s C) Csp3 + H1s D) Csp2 + H1s 54. Which atomic orbitals overlap to form the carbon-carbon and bonding molecular orbitals of ethylene, H2C=CH2? A) Csp3 + Csp3 , and C2p + C2p C) Csp2 + Csp2 , and C2p + C2p B) Csp3 + Csp3 , and Csp2 + Csp2 D) Csp2 + Csp2 , and Csp2 + Csp2 55. Which atomic orbitals overlap to form the C-H bonding molecular orbitals of acetylene, C2H2? A) Csp + H1s B) C2p +H1s C) Csp3 + H1s D) Csp2 + H1s 56. Which atomic orbitals overlap to form the carbon-carbon bonding molecular orbital of acetylene, C2H2? A) Csp2 + Csp2 B) Csp + Csp C) Csp3 + Csp3 D) C2p + C2p 57. When forming molecular orbitals from atomic orbitals, what is the order of increasing C-H bond strength for the following. A) II < I < III B) III < I < II C) III < II < I D) I < II < III 58. What is the order of decreasing bond length for a C-C bond comprised of the following molecular orbitals? A) I > III > II B) I > II > III C) III > II > I D) II > III > I
  • 14. Page 14 Chapter 1: Structure and Bonding 59. Which of the following statements about electronegativity and the periodic table is true? A) Electronegativity decreases across a row of the periodic table. B) Electronegativity increases down a column of the periodic table. C) Electronegativity increases across a row of the periodic table. D) Electronegativity does not change down a column of the periodic table. 60. Rank the following atoms in order of increasing electronegativity, putting the least electronegative first. A) I < II < III < IV C) III < II < IV < I B) I < IV < II < III D) I < II < IV < III 61. Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first. A) I > IV > II > III C) III > IV > II > I B) II > III > IV > I D) III > II > IV > I 62. Which molecule has the greatest difference in electronegativity ( E) between the two different elements? A) CO2 B) H2S C) NH3 D) H2O 63. Which compound contains the most polar bond? A) I B) II C) III D) IV 64. Which of the following compounds are non-polar? A) I, IV B) I, II C) II, III D) II, IV
  • 15. Page 15 Chapter 1: Structure and Bonding 65. Which of the following molecules has non-polar covalent bonds? A) CO2 B) N2 C) CCl4 D) HF 66. Which of the following molecules has polar covalent bonds? A) MgO B) NH3 C) Cl2 D) NaBr 67. Which of the following covalent bonds has the largest dipole moment? A) C-H B) C-C C) C-O D) H-F 68. Which of the following molecules has the smallest dipole moment? A) CO2 B) HCl C) H2O D) NH3 69. Which of the following molecules does not have a net dipole moment of zero? A) CCl4 B) BF3 C) CO2 D) NH3 70. Which of the following molecules has a net dipole moment of zero? A) I B) II C) III D) IV Chapter 2: Acids and Bases 1. Which of the following statements is a correct definition for a Brønsted-Lowry acid? A) Proton acceptor C) Electron pair acceptor B) Electron pair donor D) Proton donor 2. Which of the following statements about a Brønsted-Lowry base is true? A) The net charge may be zero, positive, or negative. B) All Brønsted-Lowry bases contain a lone pair of electrons or a bond. C) All Brønsted-Lowry bases contain a proton. D) The net charge may be zero or positive.
  • 16. Page 16 Chapter 1: Structure and Bonding 3 4 4 2 3 3. Which of the following compounds is both a Brønsted-Lowry acid and base? A) I, II B) I, III C) II, IV D) I, IV 4. Which of the following species cannot act as both a Brønsted-Lowry acid and base? A) HCO - B) HSO4 - C) HO - D) H2PO - 5. Which of the following species is not a Brønsted-Lowry base? A) BF3 B) NH3 C) H2O D) PO 3- 6. Which of the following statements about Brønsted-Lowry acids and bases is true? A) Loss of a proton from a base forms its conjugate acid. B) Loss of a proton from an acid forms its conjugate base. C) Gain of a proton by an acid forms its conjugate base. D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid. 7. Which of the following species is the conjugate base of methanol, CH3OH? A) CH3OH + B) CH3O - C) CH - D) CH4 8. Which of the following species is the conjugate base of the hydronium ion, H3O+ ? A) H3O B) H2O- C) H2O D) HO- 9. Which of the following species is the conjugate acid of ammonia, NH3? A) H4N B) H3N+ C) H2N- D) H4N+ 10. Which is the conjugate acid in the following reaction? A) I B) II C) III D) IV 11. Which is the conjugate base in the following reaction? A) I B) II C) III D) IV
  • 17. Page 17 Chapter 1: Structure and Bonding 12. Which is the conjugate acid in the following reaction? A) I B) II C) III D) IV 13. Which is the conjugate base in the following reaction? A) I B) II C) III D) IV 14. Which of the following statements about acid strength is true? A) The stronger the acid, the further the equilibrium lies to the left. B) The stronger the acid, the smaller the Ka. C) The stronger the acid, the larger the pKa. D) The stronger the acid, the smaller the pKa. 15. Which of the following compounds is the strongest acid? A) I B) II C) III D) IV 16. Which of the following compounds is the strongest acid? A) CH3OH B) BrCH2OH C) CH3NH2 D) CH3Cl 17. Which of the following compounds is the weakest acid? A) HF B) HCl C) HBr D) HI 18. Which of the following compounds is the weakest acid? A) H2S B) PH3 C) HCl D) SiH4 19. Which of the following species is the strongest base? A) HO- B) H2N- C) CH3COO- D) Cl- 20. Which of the following ranks the compounds in order of increasing basicity, putting the least basic first? A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
  • 18. Page 18 Chapter 1: Structure and Bonding B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2 21. Consider the following molecule with protons labeled, I-III. Rank these protons in order of decreasing acidity, putting the most acidic first. A) I > II > III B) I > III > II C) III > II > I D) III > I > II 22. Rank the following compounds in order of increasing acidity, putting the least acidic first. A) III < I < IV < II C) II < I < IV < III B) III < IV < I < II D) III < I < II < IV 23. Rank the following compounds in order of increasing acidity, putting the least acidic first. A) I < IV < III < II C) II < III < IV < I B) I < III < IV < II D) II < IV < III < I 24. Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) IV > II > III > I C) I > II > IV > III
  • 19. Page 19 Chapter 1: Structure and Bonding B) III > II > IV > I D) III > IV > II > I 25. Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) IV > II > III > I C) III > IV > II > I B) IV > III > II > I D) III > IV > I > II 26. Rank the following conjugate bases in order of increasing basicity, putting the least basic first. A) II < I < III B) II < III < I C) I < II < III D) I < III < II 27. Rank the following conjugate bases in order of decreasing basicity, putting the most basic first. A) II > I > III B) I > II > III C) III > I > II D) III > II > I 28. Which of the following is the strongest base? A) CH3COCH3 B) CH3COOH C) NH3 D) H2O 29. What is the direction of equilibrium when acetylene (C2H2) reacts with H2N- in an acid- base reaction? A) Left B) Right C) Neither D) Cannot be determined
  • 20. Page 20 Chapter 1: Structure and Bonding 3 30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide (CH3CH2O- ) in an acid-base reaction? A) Left B) Right C) Neither D) Cannot be determined 31. Which of the following statements explain why H2O is a stronger acid than CH4? A) H2O can form hydrogen bonds while CH4 cannot. B) H2O forms a less stable conjugate base, HO- . C) CH4 forms a more stable conjugate base, CH - . D) H2O forms a more stable conjugate base, HO- . 32. Which of the following statements explain why HBr is a stronger acid than HF? A) Br- is more stable than F- because Br- is larger than F- . B) Br- is less stable than F- because Br- is larger than F- . C) Br- is more stable than F- because Br- is less electronegative than F- . D) Br- is less stable than F- because Br- is less electronegative than F- . 33. Which of the following compounds has the lowest pKa? A) H2O B) H2S C) NH3 D) CH4 34. Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH) and ethanol (CH3CH2OH)? A) Hybridization B) Electronegativity C) Resonance D) Size 35. Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2) and ethylene (C2H4)? A) Size B) Resonance C) Inductive effect D) Hybridization 36. Which of the following concepts can be used to explain the difference in acidity between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)? A) Size B) Inductive effect C) Resonance D) Hybridization
  • 21. Page 21 Chapter 1: Structure and Bonding 37. Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) I > II > III B) III > II > I C) II > III > I D) III > I > II 38. Which of the following statements about Lewis acids is true? A) Lewis acids are proton donors. B) Lewis acids are proton acceptors. C) Lewis acids are electron pair donors. D) Lewis acids are electron pair acceptors. 39. Which of the following statements about Lewis bases is true? A) Lewis bases are electron pair acceptors. B) Lewis bases are electron pair donors. C) Lewis bases are proton donors. D) Lewis bases are proton acceptors. 40. Which of the following is a Lewis acid but not a Brønsted-Lowry acid? A) CH3OH B) H2O C) CH3COOH D) BF3 41. Which of the following species can be both Lewis acid and Lewis base? A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III 42. What is the correct classification of the following compound? CH3-O-CH3 A) Brønsted-Lowry acid and Lewis acid. C) Brønsted-Lowry base. B) Brønsted-Lowry base and Lewis base. D) Lewis base.
  • 22. Page 22 Chapter 1: Structure and Bonding 43. Identify the Lewis acid in the following reaction. A) I B) II C) III D) IV 44. Identify the Lewis base in the following reaction. A) I B) II C) III D) IV 45. Which of the following compounds is not a Lewis acid? A) AlCl3 B) HCl C) H2O D) CBr4 46. What is the role of methylchloride (CH3Cl) in the following reaction? A) Lewis acid C) Brønsted-Lowry acid B) Lewis base D) Brønsted-Lowry base 47. What is the electrophilic site in the following compounds? A) I = Carbon; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron. B) I = Chlorine; II = carbon; III = boron. D) I = Carbon; II = carbon; III = fluorine. 48. What is the nucleophilic site in the following compounds? A) I = Hydrogen; II = electrons in bond; III = nitrogen. B) I = Oxygen; II = carbon; III = nitrogen. C) I = Hydrogen; II = carbon; III = carbon.
  • 23. Page 23 Chapter 1: Structure and Bonding D) I = Oxygen; II = electrons in bond; III = nitrogen. Chapter 3: Intro. to Organic Molecules & Functional Groups 1. Which of the following lists contains common heteroatoms found in organic molecules? A) N, O, S, P, Cl C) Na, Mg, S, N, Cl B) Na, O, S, P, Cl D) Na, Mg, O, N, Cl 2. Why do heteroatoms confer reactivity on a particular molecule? A) Because they have lone pairs and create electron-rich sites on carbon. B) Because they have lone pairs and create electron-deficient sites on carbon. C) Because they are electronegative and act as electrophiles. D) Because they are electropositive and act as nucleophiles. 3. Why do bonds confer reactivity on a particular molecule? A) Because bonds are difficult to break in chemical reactions. B) Because bonds make a molecule an acid. C) Because bonds are easily broken in chemical reactions. D) Because bonds make a molecule an electrophile. 4. Which of the following molecules contain the same functional groups? A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV 5. Which of the following molecules contain the same functional groups? A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV
  • 24. Page 24 Chapter 1: Structure and Bonding 6. Which of the following molecules are aliphatic hydrocarbons? A) I, II, III B) I and III C) II, III, IV D) II and IV 7. Which of the following molecules are aromatic hydrocarbons? A) I B) II C) III D) I and III 8. Which of the following correctly matches the molecules to the names of the functional groups? I. CH3OH Carboxylic acid II. CH3CO2CH3 Ester III. CH3COCH3 Ketone IV. H2CO Alcohol A) I and II B) III and IV C) II and III D) II and IV 9. Which of the following correctly matches the molecules to the names of the functional groups? I. CH3OCH3 Ether II. CH3CONH2 Amine III. CH3SH Thiol IV. CH3CHO Alcohol A) I and II B) II and III C) III and IV D) I and III 10. Which of the following correctly matches the molecules to the names of the functional groups? I. CH3NH2 Amide II. CH3SCH3 Sulfide III. CH3CONH2 Amine IV. CH3CO2CH3 Ester A) I and II B) II and IV C) III and IV D) II and III
  • 25. Page 25 Chapter 1: Structure and Bonding 11. Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in donepezil? A) Amide, aromatic, ether, ketone. C) Amine, aromatic, ester, ketone. B) Amide, aromatic, ester, ketone. D) Amine, aromatic, ether, ketone. 12. Consider the molecule atenolol (a blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol? A) Primary alcohol, amide, primary amine, aromatic, ether. B) Secondary alcohol, amide, secondary amine, aromatic, ether. C) Secondary alcohol, amide, primary amine, aromatic, ether. D) Secondary alcohol, amide, secondary amine, aromatic, ester. 13. Which of the following structures contains a secondary amine? A) I B) II C) III D) IV 14. Which of the following structures contains a primary amine? A) I B) II C) III D) IV
  • 26. Page 26 Chapter 1: Structure and Bonding 15. Which of the following structures contains an amide? A) I B) II C) III D) IV 16. Which of the following structures contains an alkene? A) I B) II C) III D) IV 17. Which of the following is a tertiary amine? A) I B) II C) III D) IV 18. Which of the following is a secondary alcohol? A) I B) II C) III D) IV 19. Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces? A) The larger the surface area, the weaker the intermolecular force. B) The larger the surface area, the stronger the intermolecular forces. C) The smaller the surface area, the stronger the intermolecular forces. D) There is no relationship between surface area and intermolecular forces.
  • 27. Page 27 Chapter 1: Structure and Bonding 20. Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first. A) I < II < III B) II < I < III C) I < III < II D) II < III < I 21. Which of the following compounds has the lowest boiling point? A) I B) II C) III D) IV 22. Which of the following compounds has the highest boiling point? A) I B) II C) III D) IV 23. Which of the following compounds has the highest boiling point? A) I B) II C) III D) IV 24. Which of the following compounds has the highest boiling point? A) I B) II C) III D) IV
  • 28. Page 28 Chapter 1: Structure and Bonding 25. Which of the following compounds has the highest boiling point? A) I B) II C) III D) IV 26. Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first. A) I > II > III > IV C) III > II > IV > I B) III > IV > II > I D) I > IV > II > III 27. Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself? A) I B) II C) III D) IV 28. What is the strongest intermolecular force present in 1-propanol? A) Ion-ion C) Dipole-dipole B) Hydrogen bonding D) Induced dipole-induced dipole 29. What intermolecular force is generally considered the strongest? A) Hydrogen bonding C) Covalent bonds B) London dispersion forces D) Dipole-dipole 30. What intermolecular force is generally considered the weakest? A) Hydrogen bonding C) Dipole-dipole B) London dispersion forces D) Ion-ion
  • 29. Page 29 Chapter 1: Structure and Bonding 31. Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first. A) II < I < III B) I < III < II C) I < II < III D) III < II < I 32. Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first. A) I > II > III B) II > III > I C) III > II > I D) III > I > II 33. Which of the following intermolecular forces would not form between similar molecules of the structure below? A) London dispersion forces C) Hydrogen bonding B) Ion-ion D) Dipole-dipole 34. Which of the following alkanes is expected to have the highest melting point? A) I B) II C) III D) IV 35. Which of the following compounds is expected to be the least soluble in H2O? A) I B) II C) III D) IV
  • 30. Page 30 Chapter 1: Structure and Bonding 36. Which of the following compounds is expected to be the most soluble in H2O? A) I B) II C) III D) IV 37. Which of the following compounds would be expected to be more soluble in hexane (C6H14)? A) I B) II C) III D) IV 38. Which of the following statements about the solubility of organic compounds in H2O is true? A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic. B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic. C) The polar part of a molecule that can hydrogen bond to water is said to be hydrophobic. D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has 5 carbons. 39. Which of the following compounds is expected to be H2O soluble? A) I B) II C) III D) IV 40. What molecular features are required for soap to properly dissolve grease and oil? A) The molecule must be large. B) The molecule must contain a polar head. C) The molecule must contain a non-polar tail. D) B and C are required.
  • 31. Page 31 Chapter 1: Structure and Bonding 41. Which of the following statements about vitamin A, drawn below, are true? A) Vitamin A is soluble in H2O. B) Vitamin A is insoluble in organic solvents. C) Vitamin A contains an aromatic ring. D) Vitamin A is insoluble in H2O. 42. Which of the following statements about vitamin C, drawn below, are true? A) Vitamin C is insoluble in H2O. B) Vitamin C is soluble in H2O. C) Vitamin C is an aliphatic hydrocarbon. D) Vitamin C contains a ketone functional group. 43. Which of the following could most likely serve as an ionophore? A) I B) II C) III D) IV
  • 32. Page 32 Chapter 1: Structure and Bonding 44. The indicated carbon atom is: A) Electrophilic because it is electron-deficient. B) Nucleophilic because it is electron-deficient. C) Electrophilic because it is electron-rich. D) Nucleophilic because it is electron-rich. 45. The indicated bond is: A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-deficient. C) Nucleophilic because it electron-rich. D) Electrophilic because it is electron-rich. 46. The indicated bond is: A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-rich. C) Nucleophilic because it is electron-rich. D) Electrophilic because it is electron-deficient.
  • 33. Page 33 Chapter 1: Structure and Bonding 47. Which of the following list the correct functional groups found in aspartame, the artificial sweetener? A) Amine, aromatic, carboxylic acid, ether, ketone. B) Amine, amide, aromatic, carboxylic acid, ester. C) Amide, alcohol, aromatic, carboxylic acid, ether. D) Amine, aromatic, carboxylic acid, ester, nitrile. 48. Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first. A) I > III > IV > II C) IV > I > II > III B) IV > II > I > III D) I > IV > II > III Chapter 4: Alkanes 1. Which of the following statements about alkanes is not true? A) Alkanes are aliphatic hydrocarbons. B) Alkanes contain only C-C and C-H bonds. C) Alkanes are acyclic or cyclic. D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons. 2. Which of the following statements about alkanes is true? A) Alkanes are aliphatic hydrocarbons having only C-C and C-H bonds.
  • 34. Page 34 Chapter 1: Structure and Bonding B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons. C) Acyclic alkanes contain carbons joined in one or more rings. D) Acyclic alkanes have general molecular formula CnH2n. 3. What is the molecular formula of an alkane that has twenty-three carbon atoms? A) C23H46 B) C23H48 C) C23H50 D) C23H44 4. What is the molecular formula of a cycloalkane that has six carbon atoms? A) C6H14 B) C6H10 C) C6H12 D) C6H16 5. What is the approximate C-C-C bond angle in propane? A) 90° B) 109.5° C) 120° D) 180° 6. What is the hybridization of a carbon atom in an alkane? A) sp3 B) sp2 C) sp D) p 7. How many constitutional isomers are there with the molecular formula C5H12? A) 2 B) 3 C) 4 D) 5 8. How many constitutional isomers are there with the molecular formula C6H14? A) 2 B) 3 C) 4 D) 5 9. Which of the following is not another representation for 2-methylbutane? A) I B) II C) III D) IV 10. Which of the following compounds has primary, secondary, tertiary and quaternary carbon atoms? A) Pentane C) 2,2-Dimethylpentane B) 2-Methylpentane D) 2,2,3-Trimethylpentane 11. Which of the following compounds has only primary and secondary carbon atoms? A) Pentane C) 2,2-Dimethylpentane B) 2-Methylpentane D) 2,3,3-Trimethylpentane
  • 35. Page 35 Chapter 1: Structure and Bonding 12. Which of the following compounds has only primary, secondary and tertiary carbon atoms? A) Pentane C) 2,2-Dimethylpentane B) 2-Methylpentane D) 2,2,3-Trimethylpentane 13. Which of the following compounds has only primary, secondary and quaternary carbon atoms? A) Pentane C) 2,2-Dimethylpentane B) 2-Methylpentane D) 2,2,3-Trimethylpentane 14. Which of the following compounds has primary, secondary and tertiary hydrogen atoms? A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane 15. Which of the following compounds has only primary and secondary hydrogen atoms? A) 2-Methylpentane C) 3-Methylpentane B) 2,2,3-Trimethylpentane D) 2,2-Dimethylpentane 16. How many cycloalkane constitutional isomers (excluding stereoisomers) are there with molecular formula C5H10? A) 2 B) 3 C) 4 D) 5 17. What is the parent chain for the following compound? A) Hexane B) Heptane C) Octane D) Nonane 18. What is the parent chain for the following compound? A) Heptane B) Octane C) Nonane D) Decane 19. What is the name of the alkyl group that contains two carbons in a straight chain and one-carbon branch? A) Ethyl B) Propyl C) Isopropyl D) None of the above
  • 36. Page 36 Chapter 1: Structure and Bonding 20. What is the IUPAC name for the following compound? A) 4-Ethyl-5-methyloctane C) 4-Methyl-3-propylheptane B) 4-Methyl-5-ethyloctane D) 4-Methyl-5-propyloctane 21. What is the IUPAC name for the following compound? A) 3,5-Diethyl-6-methylheptane C) 3-Ethyl-5-isopropylheptane B) 3,5-Diethyl-2-methylheptane D) 5-Ethyl-3-isopropylheptane 22. What is the IUPAC name for the following compound? A) 2,3-Dimethyl-4-sec-butylheptane C) 3,5,6-Trimethyl-4-propylheptane B) 4-sec-Butyl-2,3-dimethylheptane D) 2,3,5-Trimethyl-4-propylheptane 23. What is the IUPAC name for the following compound? A) 5-Ethyl-3,6-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane B) 3-Ethyl-2,5-dimethylheptane D) 5-Ethyl-3,6-dimethyloctane
  • 37. Page 37 Chapter 1: Structure and Bonding 24. What is the IUPAC name for the following compound? A) 2,3,5-Trimethylhexane C) 2,4-Diethyl-5-methylheptane B) 2,4,5-Triethylhexane D) 4-Ethyl-3,6-dimethyloctane 25. What is the IUPAC name for the following compound? A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane 26. What is the IUPAC name for the following compound? A) 3-Ethyl-1-methylcyclohexane C) 1-Ethyl-3-methylhexane B) 1-Ethyl-3-methylcyclohexane D) 3-Ethyl-1-methylhexane 27. What is the IUPAC name for the following compound? A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane
  • 38. Page 38 Chapter 1: Structure and Bonding D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane 28. What is the IUPAC name for the following compound? A) 1,4-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane B) 1,3-Dimethylcyclohexane D) 1,4-Dimethylcyclopentane 29. What is the IUPAC name for the following compound? A) 1-Butylcyclohexane C) 1-Cyclohexylbutane B) Cyclohexanebutane D) Butylcyclohexane 30. What is the IUPAC name for the following compound? A) Hexylcyclopentane C) 1-Cyclopentylhexane B) 1-Hexylcyclopentane D) 1-Cyclopentylheptane 31. What is the IUPAC name for the following compound? A) 1-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane B) 1-sec-Butyl-3-methylcyclohexane D) 1-sec-Butyl-3-methylhexane 32. What is the common name of the following alkyl group? A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl
  • 39. Page 39 Chapter 1: Structure and Bonding 33. What is the common name of the following alkyl group? A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl 34. Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first. A) I > II > III B) I > III > II C) II > III > I D) III > II > I 35. Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first. A) I < III < II B) I < II < III C) II < III < I D) III < II < I 36. Which of the following statements about the conformations of acyclic alkanes is true? A) Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa. 37. Which of the following statements about the conformations of acyclic alkanes is not true? A) The staggered and eclipsed conformations are equally stable. B) The staggered conformations are more stable than the eclipsed conformations. C) An energy minimum and maximum occur every 60° as the conformation changes from staggered to eclipsed. D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
  • 40. Page 40 Chapter 1: Structure and Bonding 38. Which of the following statements about the conformations of acyclic alkanes is true? A) A staggered conformation with two larger groups 180° from each other is called gauche. B) Staggered conformations are at energy maxima and eclipsed conformations are energy minima. C) A staggered conformation with two larger groups 60° from each other is called anti. D) Gauche conformations are generally higher in energy than anti conformations. 39. Which of the following is not a conformer of butane? A) I B) II C) III D) IV 40. Which of the following are gauche conformers? A) I and II B) I and III C) II and IV D) II and III 41. Which of the following are anti conformers? A) I and II B) II and III C) I and IV D) II and IV
  • 41. Page 41 Chapter 1: Structure and Bonding 42. Which of the following conformers has the highest energy? A) I B) II C) III D) IV 43. Rank the conformers of butane in order of decreasing stability, putting the most stable first. A) IV > I > II > III C) II > III > I > IV B) IV > I > III > II D) I > IV > II > III 44. Which of the following is the highest energy conformer of 2,3-dimethylbutane? A) I B) II C) III D) IV 45. Which of the following is the lowest energy conformer of 2,3-dimethybutane? A) I B) II C) III D) IV
  • 42. Page 42 Chapter 1: Structure and Bonding 46. Which of the following cycloalkanes has the most angle strain? A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane 47. Which of the following cycloalkanes has the least angle strain? A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane 48. Which of the following chair conformations represents trans-1,3-dimethylcyclohexane? A) I B) II C) III D) IV 49. Which of the following chair conformations represents trans-1,4-dimethylcyclohexane? A) I B) II C) III D) IV 50. Which of the following is the most stable conformation of cis-1-ethyl-3- isopropylcyclohexane? A) I B) II C) III D) IV 51. Which of the following is the most stable conformation of trans-1-isopropyl-3- methylcyclohexane? A) I B) II C) III D) IV
  • 43. Page 43 Chapter 1: Structure and Bonding 52. Select the most stable conformer of cis-1,3-cyclohexanediol. A) I B) II C) III D) IV 53. What is the alternate chair conformation of the following compound? A) I B) II C) III D) IV 54. Which of the following is the most stable conformation of the following compound? A) I B) II C) III D) IV
  • 44. Page 44 Chapter 1: Structure and Bonding 55. Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first. A) I > II > III > IV C) III > IV > II > I B) III > II > IV > I D) I > II > IV > III 56. What are the products of the combustion of alkanes? A) Carbon and hydrogen C) Carbon dioxide and hydrogen B) Carbon and water D) Carbon dioxide and water Chapter 5: Stereochemistry 1. What is the main carbohydrate in the seeds and roots of plants? A) Starch B) Glucose C) Cellulose D) Glycogen 2. Which of the following statements about starch and cellulose is true? A) Starch and cellulose are not stereoisomers. B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. C) In starch, the O atom joins two rings using two equatorial bonds. D) In cellulose, the O atom joins two rings using two equatorial bonds. 3. Which of the following statements about constitutional isomers if not true? A) They have different IUPAC names. B) They always have the same functional groups. C) They have different physical properties. D) They have different chemical properties.
  • 45. Page 45 Chapter 1: Structure and Bonding 4. Which of the following statements about stereoisomers is not true? A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. B) Stereoisomers differ in configuration. C) Stereoisomers always have the same functional groups. D) Stereoisomers differ only in their structural formula. 5. What is the relationship between the following two compounds? A) Stereoisomers C) Identical B) Constitutional isomers D) Not isomers, different compounds 6. What is the relationship between the following two compounds? A) Constitutional isomers C) Stereoisomers B) Identical D) Not isomers, different compounds 7. What is the relationship between the following two compounds? A) Constitutional isomers C) Stereoisomers B) Identical D) Not isomers, different compounds 8. What is the relationship between the following two compounds? A) Constitutional isomers C) Identical B) Stereoisomers D) Not isomers, different compounds
  • 46. Page 46 Chapter 1: Structure and Bonding 9. Which of the following is the definition of chirality? A) The existence of a molecule with a mirror image. B) The existence of a molecule with a carbon atom that has four different substituents. C) The existence of a molecule that is superimposable on its mirror image. D) The existence of a molecule that is not superimposable on its mirror image. 10. Which of the following statements is not true? A) A molecule that is superimposable on its mirror image is said to achiral. B) A molecule that is not superimposable on its mirror image is said to be chiral. C) A molecule that is superimposable on its mirror image is said to be chiral. D) A carbon atom bonded to four different groups is a stereogenic center. 11. Which of the following statements is true? A) Enantiomers are mirror images that are not superimposable. B) A molecule that is superimposable on its mirror image is chiral. C) A chiral molecule usually contains a plane of symmetry. D) An achiral molecule does not contain a plane of symmetry. 12. Which of the following statements is true? A) Achiral molecules usually contain a plane of symmetry. B) With one tetrahedral stereogenic center, a molecule may or may not be chiral. C) With two or more stereogenic centers, a molecule is always chiral. D) Chiral molecules usually contain a plane of symmetry. 13. Which of the following is the correct definition for a pair of enantiomers? A) A pair of stereoisomers that have a plane of symmetry. B) A pair of stereoisomers that are not mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are superimposable mirror images of each other.
  • 47. Page 47 Chapter 1: Structure and Bonding 14. Which of the following molecules has a plane of symmetry? A) I B) II C) III D) IV 15. Which of the following statements is true? A) The presence of a plane of symmetry makes a molecule chiral. B) An achiral molecule must have one or more stereogenic centers. C) All molecules that have stereogenic centers are chiral. D) Stereoisomers that are not superimposable on their mirror image are enantiomers. 16. Which of the following molecules are chiral? I. cis-1,3-Dibromocyclohexane II. 1-Bromo-1-methylcyclohexane III. trans-1-Bromo-3-methylcyclohexane IV.cis-1-Bromo-3-methylcyclohexane A) I, II B) II, III C) I, IV D) III, IV 17. Which of the following molecules are chiral? I. 2-Chlorobutane II. 3-Bromopentane III. 1-Bromo-2-methylpropene IV.2-Bromo-3-methylbutane A) I, II B) I, IV C) II, III D) III, IV 18. Which of the following molecules are achiral? A) II, III B) I, II C) I, IV D) III, IV
  • 48. Page 48 Chapter 1: Structure and Bonding 19. Which of the following molecules are chiral? A) II, III B) I, II C) I, IV D) III, IV 20. How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant? A) 0 B) 1 C) 2 D) 3 21. How many stereogenic centers are present in the following compound? A) 0 B) 1 C) 2 D) 3 22. How many stereogenic centers are present in fructose, a simple sugar? A) 1 B) 2 C) 3 D) 4
  • 49. Page 49 Chapter 1: Structure and Bonding 23. How many stereogenic centers are present in the following compound? A) 1 B) 2 C) 3 D) 4 24. How many stereogenic centers are present in menthol? A) 1 B) 2 C) 3 D) 4 25. How many stereogenic centers are present in the following compound? A) 1 B) 2 C) 3 D) 4 26. How many stereogenic centers are present in the following molecule? A) 1 B) 2 C) 4 D) 5 27. How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3? A) 1 B) 2 C) 3 D) 4 28. How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3? A) 1 B) 2 C) 3 D) 4
  • 50. Page 50 Chapter 1: Structure and Bonding 29. What is the total number of possible stereoisomers for the following molecule? A) 2 B) 4 C) 6 D) 8 30. How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane? A) 2 B) 3 C) 4 D) 6 31. How many chiral stereoisomers can be drawn for dimethycyclopropane? A) 1 B) 2 C) 3 D) 4 32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain? A) 0 B) 1 C) 2 D) 3 33. How many stereogenic centers are present in the following compound? A) 0 B) 1 C) 2 D) 3 34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold- Prelog system. A) III > I > II > IV C) III > II > IV > I B) I > II > IV > III D) III > IV > II > I