Final Exam: 5/03 4-6:50 PM
Study Union: CHM 2210 Final Exam Review
1. The following molecules are related in what manner?
A) They are isotopes
B) They are constitutional isomers
C) They are the same structure
D) They are composed of different elements
E) There is no relationship
3. Considering atoms with no formal charge, which statement best describes the
valence of carbon, nitrogen, and oxygen?
A) Carbon: two bonds, zero lone pairs; nitrogen: three bonds, two lone pairs
B) Oxygen: two bonds, two lone pairs; nitrogen: three bonds, one lone pair
C) Carbon: three bonds, one lone pair; oxygen: two bonds, two lone pairs
D) Carbon: four bonds, zero lone pairs; nitrogen: two bonds, two lone pairs
E) Oxygen: three bonds, one lone pair; nitrogen: two bonds, two lone pairs
4. In which of the following does the central atom have 2 pairs of non–bonding
electrons?
A) O3
B) CO2
C) CO3 2–
D) NH4+
E) H2S
5. In ammonium, nitrogen has a valence of 4, and zero nonbonding electrons. What is
the correct formal charge of nitrogen with 4 covalent bonds?
A) –2
B) –1
C) 0
D) +1
E) +2
6. In which structure(s) below does the oxygen have a formal charge of +1?
Final Exam: 5/03 4-6:50 PM
A) I only
B) II only
C) I and III
D) I and IV
E) I, III, and IV
7. Identify the hybridized orbitals involved in formation of the C–N sigma () bond in
the following molecule known as an oxime:
A) (sp2, sp2)
B) (sp3, sp3)
C) (sp, sp)
D) (sp2, sp3)
E) There is no sigma bond between C–N.
8. From left to right, indicate the hybridization of the indicated atoms in the following
molecule:
A) I – sp ; II – sp2 ; III – sp3 ; IV – sp2
B) I – sp2 ; II – sp ; III – sp2 ; IV – sp3
C) I – sp3 ; II – sp2 ; III – sp ; IV – sp2
D) I – sp2 ; II – sp3 ; III – sp2 ; IV – sp
E) I – sp2 ; II – sp2 ; III – sp2 ; IV – sp3
9. The carbon and oxygen atoms in carbon monoxide (CO) are connected by which
type of bond(s)?
A) A sigma () bond
B) Two sigma () bonds
C) A pi () bond
D) Two pi () bonds
Final Exam: 5/03 4-6:50 PM
E) Both A and D
10. What is the approximate bond angle around the carbon in formaldehyde, a
molecule with the formula H2CO?
A) 60°
B) 90°
C) 109.5°
D) 120°
E) 180°
11. In the following reaction, how many H’s do you add or lose?
A. Add 1
B. Add 2
C. Lose 1
D. No change
12. In the following reaction, how many H’s do you add or lose?
A. Add 1
B. Add 2
C. Lose 1
D. No change
13. Which of the following structures contains an aromatic ring?
A. 1 B. 2 C. 3 D. 4
14. Which of the following pairs of structures are resonance structures?
A. 1 B. 2 C. 3 D. 4
Final Exam: 5/03 4-6:50 PM
15. Which of the following is a correct resonance structure of A?
A. 1 B. 2 C. 3 D. 4
16. Which of the following is a correct resonance structure of A?
A. 1 B. 2 C. 3 D. 4
17. Which of the following is a correct resonance structure of A?
O
O
O
O
O
O O
O
OH
O
O
A 1 2 3 4 5 A. 1 B. 2 C. 3 D. 4 E. 5
18. Which of the following is a valid resonance pair?
A)
B)
C)
D) none of the above B
19. The indicated lone pairs in the following compounds are:
Final Exam: 5/03 4-6:50 PM
i) ii) A. i) localized ii) delocalized
B. i) localized ii) localized
C. i) delocalized ii) localized
D. i) delocalized ii) delocalized
20. How many resonance structures does the following compound have (including
itself)?
A. 1 B. 2 C. 3 D. 4 E. 5
21. In the following reaction, identify the acid and base as well as the conjugate acid
and base.
i ii iii iv
A. i) Acid, ii) Base, iii) Conjugate acid, iv) Conjugate base
B. i) Base, ii) Acid, iii) Conjugate acid, iv) Conjugate base
C. i) Base, ii) Acid, iii) Conjugate base, iv) Conjugate acid
D. i) Acid, ii) Base, iii) Conjugate base, iv) Conjugate acid
E. None of the above
22. What is wrong with the following arrow?
A. It should start on the alkyne carbon.
B. It should start on a hydrogen attached to the nitrogen.
C. It should start on the anion on nitrogen, end at the H on the alkyne, and a
second arrow should start at the bond between the C and H on the alkyne and end
on the terminal carbon of the alkyne.
D. There should be two arrows – one from nitrogen and one from the alkyne
carbon.
Final Exam: 5/03 4-6:50 PM
23. Which side will the following acid-base reaction favor?
A. The right
B. The left
C. Neither
24. For the following acid-base reaction, which procedure represents the best usage of
arrow pushing and correct product formation?
O OH
Final Exam: 5/03 4-6:50 PM
O OH
H
O
+ H2O
O OH
H
O
+ H2O
O OH O
+ H2O
O OH O
+ H2O
H
H
A.
B.
C.
D.
E. None of the above C
25. Which side will the following acid-base reaction favor?
A. The right
B. The left
C. Neither
Final Exam: 5/03 4-6:50 PM
26. Identify the Lewis base in the following reaction.
A
27. Identify the Lewis base in the following reaction.
A
28. Which is the best descriptor for the following compound?
A. Bronsted-Lowry Acid
B. Bronsted-Lowry Base
C. Lewis Acid
D. Lewis Base
E. Both B and D
29. Could water protonate the following compound?
A. Yes
B. No
30. What is the IUPAC name for the following compound?
A. 2,3,5-triethylhexane
B. 2,4,5-triethylhexane
C. 2,4-diethyl-5-methylheptane
D. 4-ethyl-3,6-dimethyloctane
Final Exam: 5/03 4-6:50 PM
31. What is the IUPAC name for the following compound?
A. 1-ethyl-2-methylcyclohexane
B. 2-ethyl-1-methylcyclohexane
C. 1-ethyl-2-methylhexane
D. cyclononane
32. What is the common name of the following substituent?
A. isopropyl
B. tert-butyl
C. iso-butyl
D. sec-butyl
33. What is the IUPAC name for the following compound?
A. 3-isopropyl-5-ethylheptane
B. 2-methyl-3-ethyl-5-ethylheptane
C. 3,5-diethyl-2-methylheptane
D. 2-methyl-3,5-diethylheptane
34. How many constitutional isomers does C6H14 have?
A. 3 B.4 C.5 D.6 E.7
35. Which of the following compounds are constitutional isomers?
1 2 3 4 A. 1 and 2 B. 2 and 3 C. 3 and 4 D. 1 and 3 E. none of these
36. Using Newman projection to determine the conformation between Cl and Br
substituents in the following compound.
Final Exam: 5/03 4-6:50 PM
A. Gauche B. Anti C. Eclipsed D. Syn E. none of these
37. Which of the following is a Newman projection for the following compound as
viewed down the indicated bond?
C
38. Which of the following is the most stable conformer of the most stable isomer of
1,4-diethylcyclohexane?
C
39. Rank the following conformers of the isomers of 1-ethyl-2,4-
dimethylcyclohexane from most to least stable.
A. iii>iv>ii>i
B. ii>i>iii>iv
C. iv>i>iii>ii
D. i>iii>ii>iv
E. none of the above
40. How many chiral centers does these two compounds have in total?
A) 5 B) 6 C) 7 D) 8 E) 9
A. B. C. D.i ii iii
Final Exam: 5/03 4-6:50 PM
41. Are the following alkenes cis, trans, or neither? OMe F
Fi) ii)
A) i) trans; ii) trans
B) i) trans; ii) neither
C) i) cis; ii) trans
D) i) neither; ii) trans
E) none of the above
42. Identify the relationship between the following two structures.
A. Enantiomers
B. Identical
C. Diastereomers
D. Constitutional isomers
E. None of the above
43. which of the following is the correct structure for a compound with the IUPAC
name (R)-2-pentanol?
C
44. Which of the following is the correct IUPAC name for the following structure?
A. (S)-3-ethyl-2-methylhexane
B. (R)-3-ethyl-2-methylhexane
C. (S)-3-ethyl-2-methylpentane
D. (R)-3-ethyl-2-methylpentane
Final Exam: 5/03 4-6:50 PM
45. Rank the following from highest to lowest priority.
i) -CH3 ii) -CN iii) -CH2OH iv) -Br
A) iii>i>ii>iv
B) ii>iii>iv>i
C) iii>ii>i>iv
D) iv>iii>ii>i
E) iv>ii>iii>i
46. Identify the relationship between the following two structures.
A. Enantiomers
B. Identical
C. Diastereomers
D. Constitutional isomers
E. None of the above
47. (2R,3S)-Dibromobutane is:
A. optically active.
B. racemic.
C. dextrorotatory.
D. a meso compound.
48. Assign R or S configuration to each chirality center indicated in streptimidone.
a. (i) S; (ii) S
b. (i) S; (ii) R
c. (i) R; (ii) R
d. (i) R; (ii) S
HOH2C CHO
HO H
OHH
OHH
OHC CH2OH
H OH
HO H
HO H
(i)(ii)
Final Exam: 5/03 4-6:50 PM
49. Which of the following structures is the correct wedge/dash drawing of the
following Fischer projection?
D
50. Assign the following stereocenter as R or S.
A. R B. S C. there is no chiral center on this compound.
51. What type of cleavage does the following reaction involve?
i)
ii)
A. i) homolytic; ii) homolytic
B. i) heterolytic; ii) heterolytic
C. i) homolytic; ii) heterolytic
D. i) heterolytic; ii) homolytic
52. Why is entropy negative for ring closures?
A. Closing a ring results in fewer molecules.
B. Closing a ring results in more molecules.
C. Closing a ring releases energy.
D. Closing a ring restricts the rotation around individual carbon-carbon bonds
55. Which of the following is an energy diagram for a three step reaction? (B)
B
Final Exam: 5/03 4-6:50 PM
56. What is a transition state?
A. An isolable intermediate in a reaction.
B. The starting materials of the reaction.
C. A local maximum on the energy diagram.
D. A point between the starting materials and the product.
57. What is an intermediate?
A. A point on the reaction pathway that has a discrete lifetime.
B. A local maximum on the energy diagram.
C. A point half-way between the starting materials and products.
D. The highest energy compound on an energy diagram.
58. Identify the nucleophilic atom(s) in the following molecule?
A. carbon at the right terminus
B. oxygen
C. nitrogen
D. all of the above
E. both B and C
59. Which of the following cannot be a electrophile?
D
60. For the following reaction step, indicate which pattern it belongs to?
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
Final Exam: 5/03 4-6:50 PM
61. For the following reaction step, indicate which pattern it belongs to?
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
62. What is wrong with the following mechanism?
A. There is no leaving group, so there should be no arrows.
B. The arrow should be removing a proton from the H2O group.
C. An arrow is also needed to indicate the loss of the leaving group.
D. The arrow indicating the formation of the C-Br bond (nucleophilic attack)
should start at the bromide anion.
63. Identify the sequence of steps in the following reaction.
A. Proton transfer, Proton transfer
B. Proton transfer, Loss of leaving group
C. Nucleophilic attack, Proton transfer
D. Proton transfer, Nucleophilic attack
64. Identify the sequence of steps in the following reaction.
A. Proton transfer, Proton transfer, Nucleophilic Attack
B. Proton transfer, Nucleophilic attack, Proton transfer
C. Nucleophilic attack, Proton transfer, Loss of leaving group
D. Proton transfer, Loss of leaving group, Nucleophilic Attack
Final Exam: 5/03 4-6:50 PM
65. Which of the following is the correct IUPAC name of the following structure?
A. 2-Bromo-3-butylpentane
B. (2S)-Bromo-4,5-dimethylheptane
C. 3,4-Dimethyl-6-bromoheptane
D. 2-Bromo-4-methylhexane
66. How many primary carbons are there in the following compound?
O
F
FF
A) 1 B) 2 C) 3 D) 4 E) 5
67. Which of the following is a reasonable definition of a concerted reaction?
A. It is a reaction which takes place in a series of steps.
B. It is a reaction which produces a loud noise.
C. It is a reaction in which all bond-breaking and bond-forming occurs at the
same time.
D. It is a substitution reaction.
68. Which of the following is not a possible step in a substitution reaction?
D
Final Exam: 5/03 4-6:50 PM
69. Which of the following is the product of the following SN2 reaction?
C
70. Rank the following substrates from most to least reactive in an SN2 reaction.
A. A>B>C>D
B. D>C>B>A
C. A>C>B>D
D. D>C>B>A
71. Rank the following substrates from most to least reactive in an SN2 reaction.
A. A>B>C>D
B. C>D>B>A
C. C>B>A>D
D. D>C>B>A
72. Rank the following substrates from most to least reactive in an SN1 reaction.
A. A>B>C>D
B. A>B>D>C
C. D>A>B>C
D. D>C>B>A
Final Exam: 5/03 4-6:50 PM
73. Which of the following is the major product for the following SN1 reaction?
B
74. What type of solvent would be best for obtaining an optically active product in the
following reaction?
A. polar protic
B. polar aprotic
C. apolar aprotic
D. water
75. Which of the following is the correct IUPAC name for the following compound?
A. 2-ethyl-1,1,3-trimethylbutene
B. 3-ethyl-2,4-dimethyl-2-pentene
C. 2,4-dimethylhexene
D. 4-ethyl-1,3-dimethyl-3-pentene
76. Which of the following is the correct IUPAC name for the following compound?
A) (3S, 4Z)-3,4,5-trimethyl-4-heptene
B) (3R, 4E)-3,4,5-trimethyl-4-heptene
C) (3Z, 5S)-3,4,5-trimethyl-3-heptene
D) (3E, 5R)-3,4,5-trimethyl-3-heptene
E) none of the above
Final Exam: 5/03 4-6:50 PM
77. Is the following alkene?
A. E B. Z C. neither
78. Rank the following from most to least stable.
A) A, B, C
B) C, B, A
C) B, C, A
D) B, A, C
79. Which of the following alkyl halides would afford the indicated product upon
reaction with sodium ethoxide?
Ph
Cl
Ph
Cl
Ph
Cl
Ph
Cl
A. B. C. D.
B
80. What is the product of the following elimination?
A B C D E. none of these
C
81. Which of the following shows a mechanism for a concerted elimination?
Final Exam: 5/03 4-6:50 PM
A
82. What would be the best base for performing the following elimination?
A. NaOMe
B. NaOH
C. NaH
D. NaOtBu
E. NaNH2
83. What is the product of the following elimination?
A B C D E E
84. Which of the following alkyl halides would afford the indicated product upon
reaction with sodium ethoxide?
E. both C and D
E
85. What are the steps in the following mechanism in correct order?
Final Exam: 5/03 4-6:50 PM
A) loss of leaving group, rearrangement, proton transfer
B) concerted in one step: Proton transfer, loss of leaving group, proton transfer
C) Proton transfer, loss of leaving group, rearrangement, proton transfer
D) Proton transfer, loss of leaving group, proton transfer, rearrangement
E) none of the above
86. Which of the following is the structure of the rearranged carbocation in the
following dehydration?
B
87. The expected Markovnikov addition product of HI to 2-methyl-2-butene is:
A) 2-iodopentane
B) 2-iodo-1-methylbutane
C) 1-iodo-2-methylbutane
D) 2-iodo-2-methylbutane
E) 3-iodo-2-methylbutane
88. What is the expected major product for the following reaction?
D
Br Br
Br
Br
II III IV VI
HBr?
ROOR
A B C D E
Final Exam: 5/03 4-6:50 PM
89. Which of the alkenes below would be expected to produce a chirality center upon
hydrohalogenation in the presence of peroxide?
A)
B)
C)
D)
E)
90. Treatment of (S)-6-chloro-1-methyl-1-cyclohexene with H3O+ is expected to
produce which of the following?
A) I and III B) II C) III and V D) IV E) I, III and V
91. What is the expected major product for the following reaction?
A) B) C)
D) E)
Final Exam: 5/03 4-6:50 PM
92. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E)
93. What is the expected major product for the following reaction sequence?
D
1. BD3•THF
2. H2O2, NaOH
OH D DHO OHD D
+enantiomer
+enantiomer
+enantiomer
+enantiomer
+enantiomer
I II III IV VA B C D E
Final Exam: 5/03 4-6:50 PM
94. What is the expected major product for the following reaction?
D
96. Treating 2-methyl-2-pentene with Br2 is expected to produce which of the
following as the major product?
A) 2,3-dibromo-2-methylpentane
B) 2,2-dibromo-2-methylpentane
C) 3,3-dibromo-2-methylpentane
D) 2-bromo-2-methylpentane
E) 3-dibromo-2-methylpentane
97. The reaction of Br2 with 1-methylcyclohexene, in the presence of ethylamine
(EtNH2), is expected to produce which of the following as the major product?
Br2, CH3OH
OH
Br
H3CO
Br
Br
OCH3
OCH3
Br
I II III IV V
+enantiomer
+enantiomer
+enantiomer
+enantiomer
BrH3CO
?
A B C D E
A B C D EI II III IV V
+enantiomer
+enantiomer
+enantiomer
+enantiomer
CH3
NHEt
Br
CH3
Br
NHEt
CH3
NHEt
Br
CH3
Br
NHEt
NHEtBr
Final Exam: 5/03 4-6:50 PM
99. Of the alkenes shown, which would produce the product shown below, upon
treatment with ozone, followed by zinc metal and water?
B
100. What is the expected major product of the following reaction sequence?
C
101. What is the expected major product of the following reaction sequence?
A) B) C)
D) E)
A B C D E
CC
C
O
CC
CC
O
H
HH
HH
HH
HHH
H
H
I II III IV V
CH3 CH3 CH3
?
A B C D E
1. t-BuOK, t-BuOH
2. HBr
Cl
Br Br
Br
Br
Br Cl
I II III IV V
Final Exam: 5/03 4-6:50 PM
102. For the following reaction sequence, which molecule is an expected major
product?
A) B) C)
D) E)
103. Provide the systematic IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.
A) 1,1,5,5,5-Pentamethyl-2-pentyne
B) 1,1,1,5,5-Pentamethyl-3-pentyne
C) 2,2,6-trimethyl-4-heptyne
D) 2,6,6-trimethyl-3-heptyne
E) tert-butylisopropylacetylene
104. What is the correct IUPAC name for the molecule shown below?
A) (E)-4-isopropyloct-3-en-5-yne
B) (Z)-4-isopropyloct-3-en-5-yne
C) (E)-5-isopropyloct-5-en-3-yne
D) (Z)-5-isopropyloct-5-en-3-yne
E) (E)-4-(2-methylethyl)oct-3-en-5-yne
105. Treatment of 2,2-dibromobutane with molten KOH at 200°C would be expected
to produce which of the following?
A) (E)-2-bromo-2-butene
B) (Z)-2-bromo-2-butyne
C) 1,2-butadiene
D) 1-butyne
E) 2-butyne
Final Exam: 5/03 4-6:50 PM
106. What is the expected major organic product from treatment of 4-methyl-2-pentyne
with hydrogen in the presence of Lindlar's catalyst?
A) (E)-4-methyl-2-pentene
B) (Z)-4-methyl-2-pentene
C) (E)-2-methyl-2-pentene
D) (Z)-2-methyl-2-pentene
E) 2-methylpentane
107. What is the major expected product(s) of the reaction shown below?
A) 2,2-Dichloropentane
B) 3,3-Dichloropentane
C) 2,3-Dichloropentane
D) A and B
E) B and C
108. Which of the following alkynes would give a single product under hydroboration-
oxidation conditions?
A) 1-hexyne
B) 2-hexyne
C) 3-hexyne
D) A and B would each give a single product
E) A and C would each give a single product
109. Select the alkyne listed below that, upon treatment with ozone followed by water,
would not produce carbon dioxide and a carboxylic acid as the final products?
A) Ethyne
B) Propyne
C) 1-Butyne
D) 1-Pentyne
E) 1-Hexyne
Final Exam: 5/03 4-6:50 PM
110. Which sequence of reactions is expected to produce cis-3-octene as the final, and
major, organic product?
A) I B) II C) III D) IV E) V
111. Which sequence of reactions is expected to produce the product below as the
final, and major, organic product?
A) 1) H2, Lindlar’s cat.; 2) OsO4; 3) NaHSO3/H2O
B) 1) H2, Pt; 2) OsO4; 3) NaHSO3/H2O
C) 1) OsO4; 2) NaHSO3/H2O; 3) H2, Lindlar’s cat.
D) 1) Na, NH3(l); 2) OsO4; 3) NaHSO3/H2O
E) 1) OsO4; 2)NaHSO3/H2O; 3) Na, NH3(l)
48. Which is the product for the following SN2 reaction? Ans: D