Organic Mock Exam Questions

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OrgChem | Santiago | 2015

Organic Chemistry Mock Questions


In preparation of the Chemistry Boards 2015
Total Items: 495
Total Time: ~16.5 hrs

INSTRUCTIONS:
1. Each question is followed by five (5) answer choices. Choose the letter of the best answer.
2. Questions are rearranged such that earlier topics are reiterated all throughout the test.
3. It is best not to consult the answer key until you’ve answered all the question. Finish the
questionnaire in the allotted time.
4. Practice NO ERASURE POLICY on your answer sheet. Always choose the BEST choice among
options which can provide similar answers. All-of-the-above-none-of-the-above combo is
prevalent.
5. No act of any kind giving any examinee unfair advantage over others will be allowed.

Goodluck!
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OrgChem | Santiago | 2015

Organic Chemistry Section


1. Polarity of Covalent Bonds. Which of the following bond is the most polar?
a. C – F
b. C – Cl
c. C – N
d. C – O
e. C – H
2. Halogenation of Alkanes. Methyl chloride, CH3Cl, can be made by reaction of Cl2 with CH4 in the presence of light or heat.
Other di-, tri-, and tetrasubstituted substances may be produced as by-products. What is the best way of limiting the reaction to the
production of CH3Cl?
a. by using 1 mole CH4 and 1 mole Cl2
b. by using 1 mole CH4 and a large excess of Cl2
c. by using 1 mole Cl2 and a large excess of CH4
d. by using 4 moles of Cl2 and 1 mole CH4
e. by adding tetramethyl lead as a catalyst to an equimolar mixture of Cl2 and CH4
3. Polarity of Hydrocarbons. Which of the following hydrocarbon is the most polar?
a. CH3CH2CH2CH2CH2CH2CH2CH3
b. CH3CH2CH2CH2CH2CHCHCH3
c. CH3CHCHCH2CH2CHCHCH3
d. CH3CHCHCCCHCHCH2CH3
e. CH3CH2CH2CH2CHCHCH2CH3
4. Characteristic of Covalent Bonds. Phenolphthalein, shown in the Figure below, is used as an indicator in acid-base titrations.
Which of the following is true?
a. In terms of bond length: C > A > D > B
b. The bond angle of A involving OH is ~ 1050.
c. Only bonds A and C can be rotated.
d. In terms of bond strength: D > B > A > C
e. Choices a and d are true.

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5. Structural Effect Theory. The smell of burnt fat produced when the cooking oil is heated to its smoke point is accounted to a
substance called as acrolein, the simplest unsaturated aldehyde. It is found in biocides and is highly toxic because of the relative
nucleophilicity of C = C. This nucleophilicity can be explained by which structural effect theory?
a. Hyperconjugation
b. Inductive Effects
c. Pi electron delocalization
d. Steric Effects
e. Intermolecular forces of attraction
6. Boiling Point Comparison. From each pair, pick the compound with the higher boiling point.
i. A cis-1,2-dichloroethene or B trans-1,2-dichloroethene
j. C n-pentane or D neopentane
k. E methane or F methyl chloride
a. A, C, E
b. A, D, E
c. B, D, F
d. A, C, F
e. None of the above is correct
7. Boiling Point Comparison. Which of the following has the highest boiling point?
a. ethane
b. n-butene
c. propene
d. but-2-ene
e. n-pentene
8. Halogenation of Alkenes. 2-Methylpropene + Cl2/H2O yields
a. (CH3)2CClCH2OH
b. (CH3)2COHCH2Cl
c. 1,2-epoxy-2-methylpropane
d. CH3CH(CH2OH)CH2Cl
e. 2,3-epoxybutane

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9. Bicyclic Compounds. The number of tertiary hydrogen atoms in bicyclo[2.2.1]heptane is


a. 0
b. 1
c. 2
d. 3
e. 4
10. Zaitsav Rule of Alkene Stability. Which of the following hydrocarbon is the most stable?
a. Ethylene
b. n-Propylene
c. But-2-ene
d. n-butene
e. cyclopropane
11. Bond Length Comparison. Consider the following bonds
A. the C-C bond in ethylene
B. the C-C bond in ethane
C. the C1-C2 bond in 1,3-butadiene
D. the C2-C3 bond in 1,3-butadiene
The correct order in terms of increasing bond length (longest last) is
a. ACDB
b. ADCB
c. ABCD
d. ACBD
e. CADB
12. Volatility Comparison. Which of the following is the most volatile?
a. n-butylamine
b. n-butyl alcohol
c. diethyl ether
d. propanoic acid
e. formaldehyde

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13. Electrophilic Aromatic Substitution. Which of the following substituted benzene is the most reactive to electrophilic reagents?
a. Ar – N(CH3)2
b. Ar – NO2
c. Ar – CH3
d. Ar – Cl
e. Ar – COOH
14. Boiling Point Comparison. Which of the following has the highest boiling point?
a. n-butylamine
b. n-butyl alcohol
c. diethyl ether
d. propanoic acid
e. n-butane
15. Cycloalkanes and Angle Strain. Which of the following cycloalkanes has the highest angle strain?
a. cyclobutane
b. cyclohexane
c. cyclopropane
d. cyclopentane
e. cycloheptane
16. Acidity of Substituted Aromatic Compounds. Which of the following substituted benzoic acid is the most acidic?
a. ortho-tert-butylbenzoic acid
b. ortho-methylbenzoic acid
c. ortho-chlorobenzoic acid
d. ortho-nitrobenzoic acid
e. meta-chlorobenzoic acid
17. Hydrogens of Alkanes. Give the number of primary, secondary and tertiary hydrogens in 2,3,4-trimethylpentane.
a. 10, 15; 20, 0; 30, 3
b. 10, 12; 20, 3; 30, 3
c. 10, 12; 20, 0; 30, 4
d. 10, 12; 20, 6; 30, 0
e. none of the above is correct

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18. Oxidation of Alkene. An alkene, when heated with potassium permanganate in acid, produce adipic acid. Name the alkene.
a. isobutylene
b. cis-2-hexene
c. trans-2-hexene
d. cyclohexene
e. benzene
19. Configuration of Cycloalkanes. Which of the following has the most stable configuration? The unlabeled substituent is H.

A B C
a. A
b. B
c. C
d. A,B
e. B,C
20. Reaction of Cycloalkanes. Cyclopropane + H2O/H2SO4(catalyst) →
a. cyclopropanol
b. n-propanol
c. cyclopropanone
d. pentanal
e. bicyclo[2.1.1]hexane
21. Ozonolysis and Reductive Work-up. An alkene, C10H20, yields a mixture of 2-pentanone and 3-pentanone when treated with
ozone followed by reductive work-up. The alkene is possibly
a. 1-methyl-2-propylcyclopentadiene
b. 1,2-dimethylcyclopentane
c. 3-pentene

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d. 3-ethyl-4-methyl-3-heptene
e. (E)-3,4-dimethyl-3-hexene
22. Energy of Cycloalkanes’ Flagpole Interactions. On the basis of 0.9 kcal/mole per 1-3 CH3-H diaxial interaction, what is the
energy difference between two chair conformations of trans-1,4-dimethylcyclohexane?
a. 0.9 kcal/mole
b. 3.6 kcal/mole
c. 1.8 kcal/mole
d. 4.5 kcal/mole
e. 2.7 kcal/mole
23. Halogenation of Alkanes. The best product of the propagation reaction step CH3• + Cl2 →
a. CH3Cl + Cl-
b. CH3 + Cl2
c. CH3Cl + Cl•
d. CH3 + 2Cl•
e. CH3Cl + 1/2Cl2
24. Orbitals of Alkenes. The highest occupied molecular orbital (HOMO) of a C=C bond is
a. σ
b. π
c. σ*
d. π*
e. n
25. Comparison of Heat of Hydrogenation (Alkenes). Arrange in order of heat hydrogenation per double bond the following
compounds (most exothermic should be first)
A. Cyclohexene
B. Benzene
C. 1,3,5-hexatriene
D. 1,3-cyclohexadiene
a. BCDA
b. BDCA
c. CADB
d. ADCB
e. None of the above
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26. Structural Isomers of Alkanes. There are how many structural isomers of C6H14?
a. 5
b. 7
c. 8
d. 6
e. 9
27. Halogenation of Alkanes. Isobutane + I2/hv →
a. tert-butyliodide only
b. 2-methylpropyliodide only
c. An equal mixture of (a) and (b)
d. A mixture of (a) and (b), having (a) greater in quantity
e. No reaction
28. Rigidity of Bonds. The compound which possesses the highest energy barrier to rotation about C2-C3 axis is
a. n-hexane
b. 2,2-dimethylbutane
c. 2-methylpentane
d. n-pentane
e. neopentane
29. Percent Yield of Alkane Halogenation. The nearest percent by weight of the monochlorinated products of 2,3,4-
trimethylpentane
a. 50 %
b. 40 %
c. 83.3 %
d. 30 %
e. 90 %
30. Halogenation of Cycloalkanes. Ethylcyclohexane + Br2/heat →
a. 2-ethylcyclohexylbromide
b. 1-ethylcyclohexylbromide
c. (2-cyclohexyl)ethylbromide
d. para-bromomethylcyclohexane

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e. No reaction
31. Melting Point Comparison (Alkenes). Given the following alkenes, which of the following statement regarding their melting
point is true?
A. Trans-2-butene
B. Cis-2-butene
C. 1-butene
a. A>B>C
b. A<B<C
c. A=B>C
d. A=B<C
e. None of the above
32. Hydrogenation of Alkenes. 1,2-dimethylcyclohexene + H2, Lindlar catalyst →
a. 1,2-dimethylhexane
b. cis-1,2-dimethylcyclohexane
c. trans-1,2-dimethylcyclohexane
d. cyclohexane
e. None of the above
33. Halogenation of Cycloalkenes. Methylcyclopentene + Br2/H2O →

a. b. c. d. e.
34. Halohydrin Formation from Alkenes. Which of the following is true about the addition of HBr to an alkene in the presence of
peroxide?
a. H and Br add to the alkene following Markonikov rule
b. H and Br add to the alkene following anti-Markonikov rule
c. Rearrangement may happen along the process
d. Rearrangement does not happen along the process
e. Both (b) and (c) are true.

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35. Oxidation of Alkenes. Which of the following oxidizing reagents can oxidize alkenes to cis diols?
a. acidic KMnO4 with heat
b. cold KMnO4
c. mCPBA
d. Ozonolysis followed by a reductive work-up
e. Ozonolysis followed by an oxidative work-up
36. Ozonolysis and Reductive Work-up. C6H10 that will yield OHC(CH2)4CHO with O3/Zn, H2O
a. 1-heptene
b. 2-heptene
c. 3-heptene
d. 1-methylcyclopentene
e. cyclohexene
37. Oxidation of Cycloalkenes. Hydrolysis product of the oxidation of cyclopentene with mCPBA
a. cis-1,2-dihydroxycyclopentane
b. trans-1,2-dihydroxycyclopentane
c. pentanedioic acid
d. cyclopentene oxide
e. cyclopentanone
38. Reactions of Cycloalkenes. 1-methylcyclohexene can be converted to trans-2-methylcyclohexanol using which of the following
process/es?
a. Hg(OAc)2, H2O followed H2O2 in NaOH
b. BH3 in THF followed by NaBH4
c. H2O, H+
d. Both (a) and (c)
e. Both (b) and (c)
39. Hydroboration of Cycloalkenes. 1-methylcyclopentene + borane, followed by oxidation with alkaline H2O2 →
a. cis-2-hydroxy-1-methylcyclopentane
b. cis-1-hydroxy-2-methylcyclopentane
c. trans-2-hydroxy-1-methylcyclopentane
d. trans-1-hydroxy-2-methylcyclopentane

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e. Racemic mixture of (a) and (c)

40. Bromination of Cycloalkenes. cyclohexene + NBS →


a. pentylbromide
b. 2-bromocyclopentene
c. 3-bromocyclopentene
d. Mixture of (a) and (b)
e. Mixture of (a) and (c)
41. Alkene Polymerization. Radical polymerization of propylene occurs in this fashion
a. tail-to-tail
b. head-to-head
c. tail-to-head
d. head-to-tail
e. randomly
42. Alkene Polymerization. The stereochemical arrangement when all the methyl groups in propylene are on one side of the chain
a. syndiotactic
b. atactic
c. isotactic
d. equally distributed as (a) and (b)
e. equally distributed as (b) and (c)
43. Alkene Polymerization. The Ziegler-Natta catalysts are made up of
a. transition metal and organometal
b. transition metal salt and metal alkyl
c. Lewis base and acid
d. transition metal and an inert metal
e. noble gas and an inert metal
44. Comparison of Heat of Hydrogenation (Alkadienes). Which of the following alkadienes has the lowest ∆H of hydrogenation?

a. b. c. d. e. Both (b) and (c)


45. Bond Length Comparison. Possesses the shortest C-C single bond length

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a. ethane b. propene c. butadiene d. cycloalkane e. 1,2-dimethylhexane

46. Electrophilic Addition of Alkadienes. Which of the following is true regarding electrophilic addition of alkadienes?
a. 1,2 electrophilic addition produces a thermodynamically controlled product with a more stable product than the kinetically
favored product.
b. 1,4 electrophilic addition produces a kinetically controlled product with a more stable product than the thermodynamically
favored product.
c. 1,2 electrophilic addition produces a kinetically controlled product with a more stable intermediate than the
thermodynamically favored product.
d. 1,4 electrophilic addition produces a thermodynamically controlled product with a more stable intermediate than the
kinetically favored product.
e. Options (c) and (d) are true.
47. Electrophilic Addition of Alkadienes. CH2=CHCH=CH2 + HBr, -800C → (major product)
a. CH3CHBrCH=CH2
b. CH3CH=CHCH2Br
c. CHBr=CHCH=CH2
d. CH2BrCH2CH=CH2
e. None of the above
48. Diels-Alder Reaction. The diene and dienophile needed to synthesize the bicycloalkene shown below.
a. benzene and cyclopentadiene
b. cyclopentadiene alone
c. cyclohexene and cyclopentadiene
d. Both (a) and (b) produce the bicycloalkene
e. Both (a) and (c) produce the bicycloalkene
49. Stability of Carbanions. Which of the following carbanion is the most stable?

a. b. H2C=CH-HC=CH-CH2- c. d. H2C-CH≡C- e.
50. Polarity of Covalent Bonds. Which of the following has the most polar bond?
a. 1-butene b. 1-butyne c. butane d. 4,4-dimethyl-2-pentene e. benzene
51. Hydrogenation of Alkynes. Which of the following synthetic procedure would convert 2-pentyne to trans-2-pentene?
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a. H2/Pt b. H2, Pd/CaCO3 c. Na in NH3(liq) d. H2, Lindlar Catalyst e. All of the above
52. Diels-Alder Reaction. Which of the following substituent would make ethene a good dienophile?
a. Alkyl group b. Halide group c. Carbonyl group d. NO2 substituent e. NH2 substituent
53. Hydrohalogenation of Alkynes. CH3C≡CH + x’s HCl →
a. CH3CH2CHCl2 b. CH3CCl2CH3 c. CH3CHClCH2Cl d. A mixture of (a) and (b) e. A mixture of all
54. Hydration of Alkynes. CF3C≡CH + H2O in HgSO4, H2SO4 →
a. CF3(HO)C=CH2 b. CF3CH2CHO c. CF3(C=O)CH3 d. CF3CH2CHOH e. None of the above
55. Halogenation of Alkynes. CH3C≡CH + Cl2/CCl4→ + Br2/CCl4 →

a. b. c. d. e.
56. Markovnikov Rule. The following reactions are Anti-Markovnikov in nature except
a. Hydroboration of alkynes
b. Hydroboration of alkenes
c. Reaction of alkenes with HBr in peroxide
d. Reaction of alkynes with H2O in HgSO4/H2SO4
e. (b) and (d)
57. Oxidation of Alkynes. The following oxidation reactions would result to the same carboxylic acid except
a. CH2C≡CH reacted with O3, followed by H2O
b. CH2=CHCH2 reacted with basic OsO4, followed by hot acid
c. CH≡CCH2 reacted with basic KMnO4 followed by acidification
d. CH2=CHCH2 reacted with mCPBA, then washed with water
e. CH2=CHCH2 reacted with O3, followed by oxidative work-up
58. Test for Hydrocarbons. Which of the following hydrocarbons will not decolorize Br2 in CCl4?
a. propane
b. propene
c. propyne
d. (a) and (b)
e. (b) and (c)

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59. Ammoniacal Silver Test. Which will give a precipitate with ammoniacal silver nitrate?
a. butane
b. butane
c. 2-butene
d. butyne
e. 2-butyne
60. Aromatics. An early proposed formula for benzene
a. Huckel formula
b. Aufbau formula
c. Zaitsev formula
d. Nernst formula
e. Kekule formula
61. Comparison of Heat of Hydrogenation. Which of the following compounds has the smallest ∆H of hydrogenation?

a. b. c. d. e.
62. Aromaticity. The following are aromatic except

a. b. c. d. e. None of the above


63. Huckel Rules. Which of the following Huckel rules has been violated by [10] annulenes for it not to be considered as aromatic?
a. Planarity b. (4n+2) electrons c. Monocyclic d. Full conjugation e. All of the above
64. Stability of Aromatic Compounds. Which of the following compound is the least stable?

a. b. c. d. e.

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65. Electrophilic Aromatic Substitution. The rate determining step of the bromination of benzene is the formation of

a. (ζ+) Br…..Br….. (ζ−) FeBr b. c. d. e.


66. Reactivity of Aromatic Compounds. Which of the following statement regarding reactivity of aromatic compounds is true?
a. Substituted aromatic compounds whose substituents are electron withdrawing group can undergo electrophilic aromatic
substitution.
b. Substituted aromatic compounds whose substituents are electron donating group can undergo nucleophilic aromatic
substitution.
c. Aromatic compounds are capable of undergoing either electrophilic or nucleophilic substitution, regardless of substituents.
d. Friedel Crafts acylation and alkylation are examples of electrophilic aromatic substitution.
e. Both (a) and (b) are true.
67. Electrophilic Aromatic Substitution. The electrophile in the electrophilic nitration of benzene is
a. NO2+ b. NO2- c. NO3+ d. NO3- e. NO-
68. Electrophilic Aromatic Substitution. Which of the following substituent is the best activating group towards electrophilic
aromatic substitution (EArS)?
a. F- b. NH2- c. C≡N d. CH3 e. OCH3
69. Directing Ability of the Substituents. Which of the following substituent is not an ortho-para director?
a. C2H5 b. Cl c. OH d. COOH e. NHCOCH3
70. Electrophilic Aromatic Substitution. Which of the following substituted aromatic compound is the most susceptible to
electrophilic attack?

a. b. c. d. e.

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71. Diazotization. Which is most likely the product of the reaction:

a. b. c. d. e.
72. Halogenation and Friedel Crafts Alkylation of Aromatic Compounds. Ar-CH3 + Cl2/uv → + Ar, AlCl3 → + SO3/H2SO4

a.

b.

c.

d.
e. None of the above
73. Nucleophilic Aromatic Substitution. Substitution of the halide substituent of aromatic compounds via Nucleophilic Aromatic
Substitution (NArS) is only possible during which instance(s) given?
A. A strong electron withdrawing group is ortho to the halogen
B. A strong electron withdrawing group is para to the halogen
C. A strong electron withdrawing group is meta to the halogen
D. A strong electron donating group is ortho to the halogen
E. A strong electron donating group is para to the halogen

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F. A strong electron donating group is meta to the halogen


a. C only b. A only c. A, B d. D, E e. F only

74. Nucleophilic Aromatic Substitution on Simple Aryl Halides. Aryl halide can react with strong bases even without the presence
of electron withdrawing groups according to the equation
Ar – X + KNH2 in NH3→ Ar – NH2 + KX
The mechanism of the reaction is known as an elimination addition mechanism, passing through which intermediate?

a. b. c. d. e.

75. Sandmeyer Reactions. The Sandmeyer reaction is a series of reactions showing the versatility of which aromatic anion?

a.

b.

c.
d. (a) and (b)
e. (b) and (c)

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76. Diazotization and Sandmeyer Reactions. Aniline + NaNO3, HCl → + H3PO4 → + butane →

a.

b.

c.

d.
e. None of the above
77. Heat of Radical Formation. Which of the following has the lowest ∆H of formation?
a. alkyl benzene radical
b. tertiary radical
c. secondary radical
d. primary radical
e. vinyl radical

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78. Electrophilic Aromatic Substitution. Given the following compounds, which statement is true regarding reactivity to
electrophilic aromatic substitution?

A B C
a. A>B>C
b. A<B<C
c. C>A>B
d. C=A>B
e. C<A<B
79. Nucleophilic Aromatic Substitution. Which of the following is the most reactive towards NaNH2/NH3?

a. b. c. d. e.
80. Abstraction of H Atom. Which H atom can a Br atom abstract easiest?

c
a b d

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81. Nucleophilic Aromatic Substitution. Which substituted aryl halide will react with KH2/NH3 fastest?

a. b. c. d. All has the same reaction rate e. All won’t react


82. Nucleophilic Aromatic Substitution. Which will react with aqueous NaOH and heat?

a.

b.

c.

d.

e.

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83. Reactivity of Fused Aromatic Rings. + 1.) KMnO4, OH-, heat and 2.) H+ →

a. b. c. d. a and c e. a and b

84. Reactivity of Fused Aromatic Rings. + Cl2/hv →

a. b. c. d. e.

85. Nucleophilic Aromatic Substitution. + KOCH3 →

a. b. c. d. e. No Reaction

86. Nucleophilic Aromatic Substitution. + NaNH2/NH3 →

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a. b. c. d. e. (a) and (c)

87. Stability of Fused Ring Intermediates. Given the following fused ring intermediate, which of the following statement regarding
stability is false?

A B C

a. A < B b. C > B c. A > C d. (a) and (b) are true e. (c) is false
88. Stability of Fused Ring Intermediates. Which of the following intermediate is the most stable?

a. b. c. d. All have the same stability e. (b) & (c) are the most stable

89. Reactivity of Fused Aromatic Rings. + HNO3/H2SO4 →

a. d.

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b. e.

c.

90. Reactivity of Fused Aromatic Rings. + →

a. d.

b. e.

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c.

91. General Comparisons. Which of the following statements is false?


a. Ethane has a lower boiling point compared to chloroethane.
b. 1,1-dichloroethane is more polar than E-1,2-dichloroethane.
c. Alkyl bromide and iodide floats in water while alkyl chloride sinks.
d. CH3Cl is more soluble in polar solvents than CH4.
e. All are true.
92. Nucleophilic Substitution Reaction. Which of the following statements about nucleophilic substitution reaction is false?
a. Secondary alkyl halides can undergo both SN1 and SN2.
b. A pentacoordinated transition state can be observed for SN2 reactions.
c. A racemic mixture results from SN1 reactions.
d. The rate of SN2 reactions decrease upon substitution at α and β carbons
e. All are true
93. Bimolecular Nucleophilic Substitution Reaction. Which of the following factors promote SN2 reactions?
a. Weak nucleophiles
b. Highly ionizing protic solvents
c. A good leaving group
d. High concentration of nucleophiles
e. All promote SN2 reactions
94. Bimolecular Nucleophilic Substitution Reaction. Which of the following reagents would best react thru SN2 reaction?

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a. b. c. d. e.
95. Bimolecular Nucleophilic Substitution Reaction. Given the following set, which will proceed faster via SN2 displacement?
A. (1) CH3CH2CH2Br + CH3OH versus (2) CH3CH2CH2Br + CH3O-
B. (3) CH3CH2I + CH3S- (1.0 M) versus (4) CH3CH2I + CH3S- (2.0 M)
C. (5) CH3CH2OH + Br- versus (6) CH3CH2I + Br-
a. 135 b. 246 c. 146 d. 235 e. 145

96. Unimolecular Nucleophilic Substitution Reaction. Given the following set, which will proceed slower via SN1 displacement?
A. (1) (CH3)3CI + CH3OH versus (2) (CH3)3CCl + CH3OH
B. (3) (CH3)3CBr + H2O versus (4) (CH3)3CBr + CH3OH
C. (5) (CH3)3CCl + H2O versus (6) (CH3)2C=CHCl + H2O
a. 135 b. 246 c. 146 d. 235 e. 145
97. Nucleophilicity. Given the following set, which is the stronger nucleophile?
A. (1) OH- versus (2) CH3COO-
B. (3) CH3SH versus (4) CH3OH
C. (5) NH3 versus (6) NH4+
a. 135 b. 246 c. 146 d. 235 e. 145
98. Bimolecular Nucleophilic Substitution Reaction. Neopentyl bromide, a primary alkyl bromide, does not react SN2 when treated
with ethoxide ion in ethanol because
a. ethoxide ion is a very weak nucleophile
b. ethanol is a polar solvent so the SN1 mechanism is favored
c. the bulky t-butyl group inhibits backside attack by a nucleophile
d. rearrangement of the neopentyl carbocation to the tert-pentyl carbocation provides the driving force for the reaction to
proceed by an SN1 mechanism
e. all are possible reasons
99. Nucleophilic Substitution Reaction. Given the following set, which of the following statement is true?

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A. When an optically active halide undergoes SN2 mechanism, the resulting product is optically active.
B. When an optically active halide undergoes SN1 mechanism, the resulting product is optically inactive.
C. When an optically active halide undergoes SN1 mechanism, the resulting product is a racemic mixture.
a. A only b. B only c. C only d. A and B e. A and C
100. Stereoisomerism. Optical isomers differ in
a. sign of their optical activity
b. in their structure
c. sign and magnitude of their optical activity
d. magnitude of their optical activity
e. all of the above
101. Carbon Chirality. Which compound contains a chiral carbon?
a. n-butanol b. 2-methyl-1-butanol c. isopropyl alcohol d. 1-bromo-2-methyl-1-propane e. None of the above

102. Enantiomers. Which among the compounds can exist as enantiomers?


A. isopropyl chloride B. sec-butyl chloride C. bromochloromethane D. 1-chloro-2methylpentane
a. A, B b. B, D c. C, D d. B, C e. All of the above
For items 103-105:

A B C D
103. Enantiomers. Enantiomers
a. AB b. BC c. CD d. AD e. ABCD
104. Mesomers. Meso compounds
a. AB b. BC c. CD d. AD e. ABCD

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105. Diastereomers. Diastereomers


a. AB b. BC c. CD d. AD e. ABCD
106. Dehydrogenation of Halocompounds. Dehydrohalogenation undergoes which mechanism?
a. SN1 b. SN2 c. E1 d. E2 e. Cyclic halide mechanism
107. Elimination versus Substitution. Which of the following statements regarding nucleophilic substitution and elimination
reactions is true?
a. SN1 predominates over E1 at higher temperature for tertiary alkyl halides.
b. SN2 predominates over E2 by using stronger bases for secondary alkyl halides.
c. SN2 predominates over E2 by using unhindered strong bases for primary alkyl halides.
d. All are true.
e. All are false.

108. Method of Organic Detection. Which of the following method of organic detection can be used to detect the presence of alkyl
halides?
a. Decolorization of Br2 in CCl4
b. Formation of brown precipitate upon permanganate oxidation
c. Formation of precipitate upon reaction with ammoniacal silver nitrate
d. Formation of precipitate upon reaction with ethanolical silver nitrate
e. Effervescence upon the addition of aqua regia
109. Bimolecular Elimination Method. Which of the following would not react with concentrated alcoholic solution of KOH via
E2 elimination?
a. bromopropane
b. 2,2-dimethylbromopropane
c. 2-bromopropane
d. All will react
e. All won’t react
110. Elimination versus Substitution. tert-butyliodide + NaOH →
a. (CH3)2C=CH2
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b. tert-butyl alcohol
c. isobutylalcohol
d. 1,1,2,2-tetramethylbutane
e. No reaction
111. Elimination versus Substitution. Which of the following statement is false?
a. The reaction of ethyl iodide and potassium methoxide undergoes an SN2 mechanism.
b. The reaction of methyl chloride and potassium cyanide undergoes an SN1 mechanism.
c. The reaction of tert-butyl iodide and sodium hydroxide undergoes an E1 mechanism.
d. The reaction of methyl bromide and sodium acetate undergoes an SN2 mechanism.
e. All are false.

112. Nomenclature of Alkyl Halide. What is the correct IUPAC name for the alkyl halide which will yield pure 4-ethyl-1-hexene on
treatment with KOH/EtOH?
a. 1-chloro-3-ethylhexane
b. 2-chloro-4-ethylhexane
c. 1-chloro-4-ethylhexane
d. 6-chloro-3-ethylhexane
e. no alkyl halide can yield pure alkene under these circumstances
113. Grignard Reaction. n-propyl bromide + (1) Mg/Et2O (2) H2O →
a. n-propanol
b. n-propane
c. isopropanol
d. propene
e. hexane
114. Chirality of Molecules. Which of the following molecules are chiral?
a. trans-1,3-dimethyl-trans-2,4-dibromocyclobutane
b. trans-dimethylcyclopropane
c. cis-dimethylcyclopropane
d. All are chiral molecules

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e. All are achiral molecules


115. Reactions of Alkynes. In order to convert 3-methylbutyne to 1,2-dibromo-3-methylbutane, the following sequence should be
followed
a. Br2, then HBr
b. 2 mole HBr
c. 1 mole HBr, then HBr/peroxide
d. HBr, then Br2
e. 2 mols HBr in the presence of peroxide
116. Reactions of Aromatic Compounds. Toluene + 1. acetyl chloride/AlCl3 → 2. Zn(Hg), HCl →
a. 4-ethyltoluene
b. 3-ethyltoluene
c. 3-methylbenzyl alcohol
d. 4-methylbenzyl alcohol
e. acetophenone
117. Solubility of Alcohols. Which of the following alcohol is not soluble to water?

a. CH3CH2CH2CH2OH d.

b. HO CH2CH2CH2CH2CH2CH2OH e.
c. All are soluble to water
118. Preparation of Alcohol. Which of the following reaction results to an alcohol?
a. hydrolysis of an alkyl halide
b. oxymercuration-demercuration
c. hydroxylation of olefins
d. all of the above results to an alcohol
e. none of the above results to an alcohol
119. Chemical Properties of Alcohols. Which of the following generalizations is true?
A. Alcohols may undergo a redox reaction with highly electropositive metals where it is being reduced
B. The order of reactivity of alcohols with a redox reaction is 30>20>10
C. Alcohols are acidic than terminal alkynes but more acidic than water
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D. A primary alcohol is less basic than a secondary alcohol


a. A only b. B only c. C only d. D only e. ABCD
120. Bimolecular Nucleophilic Reaction. Which of the following is more reactive to HCl through SN2 reaction?

a. b. c. , ZnCl2 d. , ZnCl2 e. All will undergo SN1 reaction

121. Elimination versus Substitution. 2-butanol + H2SO4, 1800C →

a. d.

b. e.

c.
122. Halogenation of Alcohol with Thionyl Chloride. Which of the following statements is false regarding the reaction of R-1-
phenylpropanol with SOCl2?
a. The rate of the reaction depends both on the substrate and SOCl2.
b. The mechanism is SN1 with an ion pair intermediate collapsing fast within the reaction.
c. The product is S-1-phenylpropylchloride
d. SO2 and HCl evolution can be observed
e. The reaction proceeds slower than the reaction of R-2-butanol with SOCl2

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123. Reactions of Alcohols. Which of the following reaction is not feasible?


a. tert-butyl alcohol + PBr3 → tertbutyl bromide + PBr2OH

b. + SOCl2/pyridine → + SO2 + HCl


c. propyl alcohol + PCl3 → propyl chloride + PCl2OH

d. + SOCl2 → + SO2 + HCl

e. + H2SO4 →
124. Oxidation of Alcohols. Which of the following can oxidize primary alcohols to ketones?
A. H2Cr2O4 B. KMnO4 C. K3Cr2O4 D. PCC E. HIO4

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a. ABC b. AB c. D only d. E only E. ABCDE


125. Reaction of Alcohols. Which of the following reaction is true?
a. 2,3-dimethlybutene + O3 → H2O2 → 2 moles of 2-propanone
b. 2,2-dimethyl-2,2-dihydroxybutane + HIO4 → 2 moles of 2-propanone
c. m-methyltoluene + 1-propanal/AlCl3 → 3-(1,3-dimethylphenyl)-1-propanal
d. 1-methylcyclohexene + Hg(OAc)2, H2O → NaBH4 → 2-cyclohexanone
e. 2,3-dimethlybutene + mCPBA → H2O → 1,1,2,2-tetramethylcyclopropyl oxide
126. RedOx Reaction of Alcohols. Which of the following would react fastest with NaOH to form an alkoxide?
a. ethanol b. phenol c. tert-butyl alcohol d. paranitrophenol e. water

127. Electrophilic Aromatic Substitution. Which of the following concepts about phenolic EArS can explain why tri-substitution of
halogens is possible while tri-substitution of nitro is not?
a. Cl- defies the meta-directing ability of OH– and positions at the ortho and para, allowing tri-substitution.
b. NO2- defies the ortho-para directing ability of OH– and positions at the meta, preventing tri-substitution.
c. Cl- is too small and did not contribute much steric strain when positioned at the ortho and para compared to NO2-.
d. NO2- highly deactivates the ring right after the first substitution causing the succeeding polysubstitution not to proceed.
e. Both b and c explains the phenomenon.
128. Method of Organic Detection. Which of the following would dissolve in H2SO4, positive to Bayer’s test, and can decolorize Br2
in CCl4?
A. Ethanol B. Ethene C. Ethyne D. Chloroethane
a. ABC b. A and C c. B only d. C only d. D only
129. Reactions of Alkene. 1-octene → 1-octanol
a. H2SO4, H2O
b. 1.) Hg(OAc)2, 2.) NaBH4
c. 1.) (BH3)2, 2.) H2O2, OH-, H2O
d. All of the above are possible reagents
e. None of the above can complete the reaction
130. Reactions of Alcohol. cyclohexanol →cyclohexyl 2-butyl ether
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a. 2-butanol, H2SO4
b. 1.) PBr3, 2.) Butanol, NaOH
c. 1.) 2-butene, Hg(CF3COO)2, 2.) NaBH4
d. All of the above are possible reagents
e. None of the above can complete the reaction
131. Discriminating Reagent. Which compound can best differentiate tert-butyl alcohol and 1-butanol?
A. SOCl2 B. PCl3 C. Lucas Reagent D. I2, ROH E. H2SO4, CrO3
a. A and B b. B and C c. C and D d. D and E E. ABCDE

132. Volatility of Compounds. Given the 3 compounds below, which statement is true?

A B C
a. A is more volatile than C
b. B is more volatile than A
c. B is more volatile than C
d. A is less volatile than B
e. All are false statements
133. Synthesis of Ethers. Which of the following reactions won’t result to an ether/epoxide?
a. Ethanol + Sulfuric acid at 1800C
b. 2-methyl-1-butene undergoing methoxide mercuration-demercuration reaction
c. Phenol + 1.) Na, 2.) 2-chloroethane
d. 2-methylpropene + 1.) Cl2, water, 2.) NaOH

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e. All will yield an ether or an epoxide


134. General Concepts About Ethers. Which of the following statements is true?
a. Diethyl ether can produce two moles of ethyl chloride when reacted with HCl via SN1 mechanism.
b. Ethoxy groups are moderately deactivating in aromatic ethers and direct electrophilic attacks to the meta position.
c. Protonation of the O atom weakens the carbonyl bond put a partially positive charge on the beta carbon, making it a good
site for nucleophilic attacks.
d. Ether, alkanes, alkenes and alcohol dissolve in sulfuric acid.
e. All statements are false.

135. Hydration of Epoxides. + H2O/H+ →

a. b. c. d. e. Mixture of a and b

136. Hydrohalogenation of Ethers. + excess HBr →


a. benzylbromide + 2,4,5-tribromophenol
b. benzylbromide + bromobenzyl
c. benzylbromide + phenol
d. benzylbromide + bromobenzene
e. 2,4,5-tribromobenzylbromide + 2,4,5-tribromophenol
137. William Ether Synthesis. t-butylchloride + sodium methoxide
a. methyl-t-butyl ether

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b. 2-methylpentene
c. dimethyl ether
d. All are possible product
e. None of the above
138. Discriminating Reagent. Which reagent will differentiate methoxybenzene and ethylbenzene?
a. Bromine, hv
b. AlCl3, ethyl chloride
c. sulfuric acid
d. a and b
e. a and c

139. Stepwise Synthesis. + RCOOOH → H3O+ → HIO4 →

a. 2 moles of benzoic acid d.

b. e. None of the above


c. 2 moles of benzaldehyde
140. Crown Ethers. Name of the ether in the figure.
a. 8-crown-4
b. 4-crown-8
c. 4,8-crown
d. 8,4-crown
e. None of the above
141. Method of Organic Detection. Which of the following reagents or tests cannot be used to detect ethers/epoxides?
a. sulfuric acid b. Bromine in CCl4 c. Zelsel Method d. Concentrated HX e. Bayer’s Test
142. Reactions of Phenols. Phenol + NaH/THF → BrCH2CH=CH2
a. 3-but-1-enyl phenyl ether

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b. ortho-(3-but-1-enyl)phenol
c. para-(3-but-1-enyl)phenol
d. A mixture of a and b
e. A mixture of b and c
143. Nomenclature of Multi-Functional Compounds. The IUPAC name for CH3(CO)CH2CH2CH=CH2
a. 1-penten-4-one
b. 4-penten-2-one
c. methyl-3-butanone
d. 3-ketoethyl-1-propene
e. None of the above
144. Comparison of Organic Compounds. Which of the following generalizations is true?
a. n-propyl alcohol is more volatile than methyl ethyl ether
b. methyl ethyl ether is more soluble in water than n-propyl alcohol
c. methyl ethyl ether is more polar than propanal
d. propanal has a higher boiling point than n-propyl alcohol
e. None are true
145. Reactions of Alkynes. 2-butyne → 2-butanone
a. Hg(OAc)2, H2O, H+
b. 1.) ozone, 2.) Zn, water
c. H2CrO4, H2SO4
d. 1.) ozone, 2.) H2O2, OH-
e. (BH3)2, H2O2, OH-
146. Reactions of Alcohols. 2-phenylethanol → phenylacetaldehyde
a. KMnO4
b. Cr2O4, H2SO4
c. OsO4
d. chromic oxide, pyridine, HCl
e. HIO4
147. Nucleophilic Addition on Carbonyls. Which of the following statements is true regarding nucleophilic addition reactions on
carbonyl compounds?
a. The rate of nucleophilic reaction increases with the addition of acid, as it protonates the oxygen of the carbonyl bond and
makes the C atom more electrophilic.

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b. The larger the alkyl chain, the slower is the reaction, as it crowds the transition state.
c. Reactivity is increased when an electron withdrawing groups like halogens are attached to the carbonyl group.
d. All statements are true.
e. All statements are false.
148. Nucleophilic Addition on Carbonyls. Which of the following nucleophilic addition reactions cannot be reversed?
a. cyanohydrin reaction (HCN addition)
b. bisulfite reaction (NaHSO3 addition)
c. Hydration (addition of water)
d. Reduction (NaBH4/LiAlH4)
e. All reactions are reversible.
149. Reactions of Alcohols. n-pentanol + PCC → + HCN → + LiAlH4 →
a. 2-hexanol
b. 2-cyano-2-hexanol
c. 2-amino-2-hexanol
d. hexane
e. None of the above
150. Discriminating Reagent. Which reagent/s will differentiate 2-pentanone from pentanal?
a. Sodium cyanide
b. Sodium bisulfite
c. Iodine, KOH
d. a and b
e. b and c
151. Acetals and Ketals. Ketals are formed from a ketone and 2 molecules of
a. amine b. water c. alcohol d. carboxylic acid e. alkyl halide
152. Acetals and Ketals. Acetals are used as masking agent against
a. corrosion b. bases c. acids d. oxidizing agents e. reducing agents
153. Reactions of Carbonyl Compounds. acetaldehyde → lactic acid (CH3CHOHCOOH)
a. ethanol, H+
b. 1.) sodium bisulfite, 2.) acid, water
c. 1.) HCN, 2.) H+, H2O
d. 1.) HCN, 2.) LiAlH4
e. KMnO4

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154. Acid-catalyzed Hydrolysis. Acid hydrolysis of will result to


a. phenyl hydrazine, acetophenone
b. aniline, acetophenone
c. aniline, 1-phenyl ethanol
d. phenyl hydrazine, 1-phenylethanol
e. The compound is resistant to acid hydrolysis

155. Nucleophilic Addition on Carbonyl Bonds. Which of the following is the most reactive towards nucleophilic addition?
a. para-methylbenzaldehyde
b. para-chlorobenzaldehyde
c. para-Br(C6H4)(CH2CHO)
d. para-nitrobenzaldehyde
e. para-(NO2)(C6H4)(CH2CHO)
156. Osazone and Derivatives. The product of the reaction (CH3)2C=O + NH2(C=O)NHNH2
a. (CH3)2C=N(C=O)NHNH2
b. (CH3)2(C-OH)NHNH(C=O)NH2
c. (CH3)2C=NNHCNH2
d. Mixture of a and b
e. Mixture of b and c
157. Synthesis of Alcohols. Which of the following would result to 2-methyl-2-hexanol?
a. formaldehyde with sec-butylbromide
b. acetaldehyde with isobutylbromide
c. acetone with butylbromide
d. 2-hexanone with bromoethane
e. None of the above
158. Lewis Acid Catalysts. The following compounds are used as Lewis acid catalysts in organic reactions except
a. SnCl4 b. FeBr3 c. BF3 d. CH3MgBr e. All are catalysts
159. Interference on Grignard Reactions. Which of the following functional groups may interfere with the attack of RMgX on
carbonyl sites?

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a. –C=N− b. –Cl c. –SH d. –NO2 e. All groups interfere


160. Oxidation of Carbonyl Groups. Which of the following modes of oxidizing carbonyl compounds is true?
a. Strong oxidizing agents such as permanganate and dichromate salts can oxidize ketones to carboxylic acids.
b. Tollen’s reagent oxidizes aldehydes but leaves alkenes untouched.
c. Ketones can be oxidized via Baeyer-Villager method, producing carboxylic acids.
d. All statements are true.
e. All statements are false.

161. Special Reactions of Carbonyl Compounds. Benzaldehyde, in the presence of a strong base, is most likely to undergo which of
the following reactions
a. Canizzaro Reaction
b. Aldol Condensation
c. Baeyer-Villager Oxidation
d. Catalytic Hydrogenation
e. None of the above
162. Cross Canizzaro Reaction. Benzaldehyde + formaldehyde + conc. NaOH →
a. benzoic acid
b. 1,2-dihydroxy-1-phenylethane
c. benzyl alcohol
d. A mixture of a and c
e. A mixture of b and c
163. Baeyer-Villager Oxidation. 1-chloro-2-propanone + hydrogen peroxide →
a. α-chloromethyl acetate
b. α-chloroacetic acid
c. chloromethyl acetate
d. methyl-α-chloroacetate
e. none of the above
164. Differences in Reducing Power. Which of the following statements about common reducing agents is true?
a. LiAlH4 requires a protic solvent to work.
b. NaBH4 requires aprotic solvent to work.
c. LiAlH4 leaves double and triple bonds untouched but oxidizes α,β-unsaturation
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d. NaBH4 oxidizes double and triple bonds but leaves α,β-unsaturation


e. All are true
165. Clemmensen versus Wolf-Kishner. Which of the following statements is true?
a. Clemmensen reduction is used to reduce compounds reactive to bases, using Zn, Hg and conc. HCl.
b. Wolf-Kishner reduction is used to reduce compounds reactive to acids, using hydrazine, KOH and water.
c. Both mode of reduction reduces carbonyl compounds to hydrocarbons.
d. All statements are true.
e. All statements are false.

166. Reduction of Ketones. Cyclohexanone → Cyclohexane


a. 1.) LiAlH4 2.) KOH, H2O
b. 1.) NH2NH2 2.) KOH, H2O
c. Lindlar Catalyst
d. NaBH4
e. None of the above
167. Oxidation of Ketones. 3-methyl-2-butanone → isobutyric acid
a. Br2, KOH
b. H2O2, KOH, H2O
c. 1.) LiAlH4 2.) concentrated HCl, Zn, Hg
d. conc. NaOH
e. KMnO4, H+
168. Wittig Reaction. methylene trophenyl phosphine + 2-butanone →
a. 2-butanol
b. 2-methyl-1-butene
c. tri-2-butylphosphine
d. 2-methyl-2-butene
e. None of the above
169. Lithium Aluminum Hydride. Lithium aluminum hydride is useful for the reduction of
a. carboxylic acids
b. esters
c. aldehydes
d. enone

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e. all of the above


170. Oxidation of Carbonyl Compounds. Which of the following compounds is (are) readily oxidizable?
a. propanone
b. cyclohexanone
c. acetaldehyde
d. benzophenone
e. all are readily oxidizable

171. Hypohalite Reaction. (C6H5)CH=CCH3(C=O)CH3 + NaOI →


a. (C6H5)CH=CCH3(C=O)COOH
b. CH3COOH
c. (C6H5)CH=CCH3(C=O)OCH3
d. (C6H5)CH=CCH3O(C=O)CH3
e. No reaction
172. Methyketones. Acetophenone may be monobrominated using
a. Bromine and sodium hydroxide
b. Bromine and acetic acid
c. NBS
d. All can produce a monobrominated product
e. All produce a polybrominated product
173. Method of Organic Detection. Ammoniacal silver nitrate converts an aldehyde to
a. a primary alcohol
b. a carboxylic acid
c. a nitroalkyl
d. a ketone
e. a silver complex which precipitates from the solution
174. Reactions of Carbonyl Compounds. Acetyl acetone is most readily alkylated
a. at the central carbon
b. with tertiary alkyl halides
c. in ethanol solution
d. All are necessary conditions for optimum alkylation of acetyl acetone

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e. All inhibits the alkylation of acetyl acetone


175. Michael Addition. Which is the best reagent for the conversion of acrolein to 3-methoxy propanal?
a. 1.) Methanol, HCl 2.) Aqueous acid
b. Methanol, benzoyl peroxide, light
c. 1.) Sodium methoxide 2.) Water
d. All converts acrolein with the same reaction rate
e. All will not convert acrolein at all

176. Aldol Condensation. Aldol condensation of acetaldehyde with basic catalysts produces
a. butanoic acid
b. 3-hydroxybutanal
c. butanal
d. 2-butanone
e. The reaction won’t proceed; acidic catalyst should have been used
177. α-β Unsaturated Ketones. p-methoxyaniline + acrolein + phosphoric acid →
a. 2-methoxyquinoline
b. 1-methoxyisoquinoline
c. 5-methoxyquinoline
d. N-(p-methoxyphenyl)acrylamide
e. 6-methoxyquinoline
178. Base Catalyzed Hydrolysis of Epoxides. methyl-β-D-ribofuranoside + sodium hydroxide + water →
a. methanol + D-ribose
b. methyl-α-D-ribofuranoside
c. methyl-β-L-ribofuranoside
d. dimethyl ether + maltose
e. no reaction
179. Nucleophilic Addition on Carbonyl Compounds. glycine + 1.) benzoyl chloride + 2.) acetic anhydride
a. glycyl anhydride
b. hippuric acid
c. N-benzoylglycine acetate
d. phenylalanine

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e. none of the above


180. Osazone and Derivatives. D-ribose + excess phenylhydrazine →
a. D-ribose phenylhydrazine
b. D-erythrose
c. D-erythrose osazone
d. β-D-ribose
e. D-arabinose osazone

181. Nucleophilic Addition on Carbonyl Compounds. cyclohexanone + 1.) piperedine + 2.) methyl iodide + 3.) aqueous acid
a. N-methylpiperedine
b. 2-methylcyclohexanone
c. 1-methylcyclohexene
d. methylcyclohexane
e. 1-methylcyclohexanol
182. Osazone and Derivatives. alanine + dicyclohexylcarbodiimide (shown in the Figure below)
a. alanylalanine + dicyclohexyl urea
b. cyclohexyl alaninate
c. N-cyclohexylalanine
d. dicyclohexyl carbonate + alanylalanine
e. none of the above
183. Nucleophilic Addition on Carbonyl Compounds. alanine + 1 equivalent benzyl chloroformate →
a. N-carbobenzyloxyalanine
b. alanyl carbobenzyloxyl anhydride
c. benzyl alaninate
d. benzyl chloride
e. N-benzylalanine
184. Nucleophilic Addition on Carbonyl Compounds. D-ribose → methyl-α-D-ribofuranoside
a. p-toluenesulfonic acid, methanol
b. methyl iodide, sodium hydroxide
c. methanol, dicyclohexylcarbodiimide
d. diazomethane

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e. methanol, sodium hydroxide


185. Nucleophilic Addition on Carbonyl Compounds. acetaldehyde → alanine
a. 1.) ammonia, 2.) carbon dioxide
b. 1.) sodium cyanide, water, 2.) sodium hydroxide
c. 1.) sodium cyanide, ammonia, 2.) aqueous acid
d. 1.) sodium amide, 2.) carbon dioxide
e. 1.) sodium permanganate, 2.) ammonia

186. Reactions of Dienes. 1,3-butadiene → 4-vinylcyclohexene


a. 1.) acrolene, sodium methoxide, 2.) methyl Grignard
b. 1.) ethylene, 2.) palladium, nitrogen
c. heat
d. acetylene, heat
e. 1.) cyclohexene, 2.) potassium permanganate, 3.) hydrogen, platinum
187. Nucleophilic Addition on Carbonyl Compounds. benzaldehyde → 2-phenylindole
a. indole, sodium amide
b. 1.) aniline, 2.) sulfuric acid
c. 1.) o-toluidine, 2.) sulfuric acid
d. 1.) phenylhydrazine, 2.) acid
e. 1.) o-aminobenzaldehyde, 2.) sulfuric acid
188. Reactions of Carboxylic Acids. butyric acid → n-propylamine
a. 1.) thionyl chloride, 2.) sodium amide
b. 1.) sodium permanganate, 2.) thionyl chloride, 3.) ammonia
c. 1.) thionyl chloride, 2.) ammonia, 3.) bromine, aqueous sodium hydroxide
d. 1.) bromine, 2.) potassium phththalimide, 3.) aqueous acid
e. 1.) dicyclohexylcarbodiimide, 2. ammonia
189. Reactions of Cycloalkenes. cis-3,4-dimethylcyclobutene → cis,trans-1,4-dimethyl-1,3-butadiene
a. aluminum chloride
b. platinum oxide, nitrogen
c. silver oxide
d. heat

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e. light
190. Nucleophilic Addition on Carbonyl Compounds. acrolein → 3-methoxypropanal
a. 1.) methanol, hydrogen chloride, 2.) aqueous acid
b. sodium methoxide
c. 1.) hydrogen peroxide, 2.) sodium hydroxide, methyl iodide
d. 1.) hydrogen chloride, 2.) sodium methoxide
e. methanol, benzoyl peroxide, light

191. Molecular Orbitals of Conjugated Systems. The LUMO of 1,3-butadiene has _____ nodes.
a. -1
b. 0
c. 1
d. 2
e. 3
192. Chirality. Sucrose contains ______ chiral centers.
a. 10
b. 6
c. 4
d. 9
e. 12
193. Stereochemistry of Sugars. Methyl-α-D-ribofuranoside and methyl-β-D-ribofuranoside are
a. carbohydrates
b. reducing sugars
c. hormones
d. anomers
e. esters
194. Structural Effect. Enol forms of β-diketones are stabilized by
a. π delocalization
b. hydrogen bonding
c. dimer formation
d. charge dispersal

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e. the β-effect
195. Carboxylic Acids and Derivatives. The following are considered as carboxylic acid and derivatives except
a. formic acid
b. benzoyl chloride
c. ethyl propanoate
d. 2-methoxy-2-methylpropane
e. All are carboxylic acids and derivatives.

196. Acidity of CADs. Which of the following carboxylic acid derivatives has the most acidic α hydrogen?
a. CH3CH2COOH
b. CH3CH2COCl
c. CH3CH2COOCH3
d. CH3CH2COSH
e. CH2(CO)O(CO)CH2
197. Solubility of Organic Compounds. The following are soluble to water except
a. adipic acid
b. 2,3,5,6-tetrahydroxocyclohexanone
c. 2-hydroxohexanoic acid
d. 2-hydroxohexanal
e. All are soluble to water
198. Preparation of Carboxylic Acids. Which of the following reactions won’t yield carboxylic acids?
a. Ozonolysis followed by oxidative work-up
b. Oxidation of alkenes by cold KMnO4
c. Canizzaro Reaction
d. Haloform Reaction, followed by aqueous acid
e. Carbonation of Grignard Reaction
199. Acidity of CADs. Which of the following is the least acidic?
a. phenol
b. benzyl alcohol
c. water
d. methyl phenyl ester

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e. benzoic acid
200. Solubility. Which of the following carboxylic acid derivatives is insoluble to 10% NaOH?
a. propanoic acid
b. phenol
c. 3-pentanol
d. 2,2-difluoropropanoic acid
e. all are soluble to 10% NaOH

201. Acidity of CADs and Structural Effect. Which of the following is the least acidic?
a. propanoic acid
b. phenol
c. 2-nitrophenol
d. 4-nitrophenol
e. water
202. Boiling Point Comparison. Which of the following organic compounds has the highest boiling point?
a. propanoic acid
b. methyl propyl ether
c. butanol
d. 2-methylpropanal
e. propanoyl chloride
203. Nucleophilic Substitution on Acyl Compounds. Which of the following statements is false?
a. Nucleophilic substitution occurs at the carbonyl carbon and replaces the OH bond with stronger nucleophiles, producing
carboxylic acid derivatives.
b. At high temperatures, amides can be formed from the direct reaction of carboxylic acids and ammonia.
c. Amide formation is not possible when acyl chloride is made to react with ammonia due to issues about the leaving group.
d. Both a and b are considered false
e. Both b and c are considered false
204. Anhydride Preparation. The following would result to an anhydride except
a. RCOOH + RCOCl in pyridine
b. RCOOH + AlPO4, ∆
c. RCOOH + acetic anhydride, ∆

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d. R(COOH)2 + ∆
e. All will yield an anhydride
205. Reactions of Carboxylic Acids. benzoic acid + NH3, ∆ →
a. 2-aminobenzoic acid
b. 3-aminobenzamide
c. benzamide
d. aniline
e. no reaction

206. Reactions of Carboxylic Acids. Product of the self-condensation reaction of a carboxylic acid is
a. ethers
b. esters
c. anhydride
d. none of the above
e. the reaction isn’t feasible at all
207. Boiling Point Comparison. Which of the following has the lowest boiling point?
a. HOOC(CH2)3COOH
b. H2NCO(CH2)3CONH2
c. ClCOCH2COCl
d. (CH3)2NCOCH2CON(CH3)2
e. H3CCOOCOCH3
208. Boiling Point Comparison. Which of the following organic compound has the highest boiling point?
a. propanamide
b. N,N-dimethylpropanamide
c. N-methylpropanamide
d. propionic anhydride
e. propionic acid
209. Boiling Point Comparison. Given the following set of compounds, which of the following statement is true regarding their
boiling points.
A. dimethyl ketone B. propanol C. ethanoic acid
a. A>B>C
b. A<B<C

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c. B>A>C
d. A>C>B
e. C>A>B

210. Nucleophilic Substitution on Acyl Halides. The following compounds will readily replace the hydroxyl group in the acyl
halide except
a. Grignard Reagent
b. water
c. AlCl3, benzene
d. ester in an aqueous base
e. all can act as a nucleophile
211. Nucleophilic Substitution on Acyl Halides. propionic acid → 3-pentanone
a. 1.) EtMgBr, 2.) aqueous acid
b. 1.) PCl3, 2.) EtMgBr
c. 1.) SOCl2, 2.) Et2Cd
d. EtOH, KOH
e. None of the above
212. Nucleophilic Substitution on Acyl Halides. butyric acid → ethyl butyrate
a. 1.) EtOH, 2.) KOH
b. 1.) SOCl2, 2.) EtOH
c. 1.) KOH, 2.) EtCl
d. EtOH, H+
e. none of the above
213. Nucleophilic Substitution on Acyl Halides. HOAc + SOCl2 → + CH3MgCl →
a. dimethyl ether
b. dimethyl ester
c. t-butyl alcohol
d. isopropanol

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e. none of the above

214. Nucleophilic Substitution on Acid Anhydrides. succinic acid anhydride + CH3OH →

a.

b.

c.

d.
e. none of the above
215. Acid Hydrolysis of Esters. Which of the following statement regarding acid hydrolysis of ester is true?
a. Only esters having primary alkyl substituent can produce carboxylic acid and alcohol products.
b. Esters having primary and secondary alkyl substituents require the protonation of the esterific oxygen, making the alkyl
substituent a better leaving group as a primary and secondary alcohol.
c. Esters having tertiary alkyl substituent require the protonation of the carbonyl oxygen, making the attack of the water
molecule more possible by increasing the positivity of the carbonyl carbon.
d. All are true.
e. None are true.

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216. Hydrolysis of Esters. Which of the following statements regarding hydrolysis of esters is true?
a. Electron donating groups, such as the halogens, decrease the rate of ester hydrolysis because they make the carbonyl group
more negative.
b. Electron withdrawing groups, such as the nitro substituents, increase the rate of ester hydrolysis because they make the
carbonyl group more nucleophilic.
c. Acid catalyzed ester hydrolysis is reversible while base catalyzed hydrolysis is not.
d. All are true.
e. None are true.
217. Nucleophilic Acyl Substitution on Esters. Which of the following reactions is not possible?
a. An amide can be formed by reacting an ester with an amine.
b. Only tertiary alcohols result from the reaction of an ester with Grignard reagent.
c. Only primary alcohols result from the reduction of ester by LiAlH4.
d. Only secondary alcohols result from the reaction of an ester with hydrogen gas and Ni.
e. All reactions are possible.
218. Reactivity due to α-Hydrogen. The following reaction results because of the acidity of the α-Hydrogen except
a. Claisen Condensation
b. Dieckmann Condensation
c. Crossed Claisen Condensation
d. Crossed Dieckmann Condensation
e. All are reactions due to the acidity of α-H
219. Esterific Terms. An activated acetic acid is also called
a. acetoacetic ester
b. malonic ester
c. succinic ester
d. ethyl acetoacetic ester
e. none of the above

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220. Dieckmann Condensation. Et-O-(C=O)-(CH2)4-(C=O)-O-Et + NaOEt →

a.
b. Na+ -O2C(CH2)4CO2- Na+

c.

d.

e.
221. α-β Unsaturated Aldehydes. Acrolein → H2C=CHCH=CHCOOH
a. (1) NaOAc, (CH3CO)2O, (2) water
b. (1) NaCN, H2O, (2) EtMgBr, ether
c. (1) EtMgBr, ether, (2) CO2
d. Reaction not possible
e. None of the above

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222. Nucleophilic Acyl Addition on Aldehydes. NaCH(COOEt)2 + benzaldehyde


a. Ar-CH(COOEt)2
b. Ar-CH2CH2COOEt
c. Ar-CH=C(COOEt)2
d. Reaction not possible
e. None of the above

223. Malonic Ester Acid Synthesis. H2C(COOC2H5)2 → (CH3)2CHCH2CH2COOH


a. (1) NaOAc/ethanol (2) propyl chloride (3) t-butylO-Na+ (4) Methyl chloride (5) OH-/water (6) H+ (7) ∆
b. NaOAc/ethanol
c. (1) NaOAc/ethanol (2) (CH3)2CHCH2Cl (3) OH-/water (4) H+ (5) ∆
d. (1) NaOAc/ethanol (2) (CH3)2CHCH2CH2Cl (3) OH-/water (4) H+ (5) ∆
e. None of the above
224. Hell-Volhard-Zelinsky Reaction. (CH3)2CHCOOH + PBr3, Br2 →
a. 2-methylpropene
b. 2-methyl-1-bromopropane
c. 2-bromo-2-methylpropionic acid
d. 3-bromo-2-methylpropionic acid
e. 1-methylpropanoyl chloride
225. Reformatsky Reaction. BrCHCOOEt + 2-butanone, Zn →

a.
b. CH3CH2CH=CHCH2COOEt
c. (CH3CH2)(CH3)C=CHCOOEt
d. CH3CH2CHC=C(CH3)(COOEt)
e. none of the above
226. Reduction of Carboxylic Acids. CH2=CHCH2COOH → CH2=CHCH2CH2OH
a. H2, Ni
b. LiAlH4
c. H2, Pd/CaCO3

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d. All can push the selective reduction


e. None can comply with the selective reduction
227. From Alkyl halides to Carboxylic Acids. 1-bromoheptane → octanoic acid
a. (1) NaCN (2) Sulfuric Acid, Water
b. (1) Mg, ether (2) Formaldehyde
c. (1) Methyl Lithium (2) KMnO4
d. (1) Li (2) Formic Acid
e. CO2, sulfuric acid
228. From Ketones to Amines. 2-butanone → 2-butylamine
a. sodium amide
b. (1) NaCN, (2) H2SO4
c. H2SO4, NaCN
d. (1) ammonia (2) H2, palladium on charcoal
e. (1) Sodium bisulfite (2) ammonia
229. From Carboxylic Acid to its Derivative, Ester. butyric acid → ethyl butyrate
a. ethanol, KOH
b. (1) SOCl2 (2) ethanol
c. H2SO4, ∆
d. (1) NH3 (2) ethanol
e. (1) KOH (2) Ethyl Chloride
230. α-Halogenation of Ketones. acetone → monobromoacetone
a. HBr, sulfuric acid
b. Bromine, KOH
c. PBr3, Br2
d. Bromine in CCl4
e. Bromine in HOAc
231. Stepwise Synthesis. ethyl bromide → propiophenone
a. (1) NaCN, DMSO (2) phenyl Grignard (3) water
b. NaOH, acetophenone
c. (1) Mg, ether (2) acetophenone
d. (1) formaldehyde, NaOH (2) bromobenzene, water
e. (1) formaldehyde, NaOH (2) AlCl3, benzene

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232. Reactions on α-β Unsaturations. acrolein → 2,4-pentadienoic acid


a. cyclopentadiene, KMnO4
b. (1) ethyl Grignard, ether (2) carbon dioxide
c. (1) NaOH (2) H2SO4, heat
d. NaOAc, acetic anhydride
e. (1) NaCN, water (2) ethyl Grignard, ether

233. Grignard Reaction. proprionic acid + ethyl magnesium bromide →


a. propane + HOAc
b. bromomagnesium proprionate + ethane
c. 3-pentanone
d. pentanoic acid
e. pentane
234. Reactions of Anhydride. toluene + (1) chromic anhydride, acetic anhydride (2) aqueous acid →
a. benzoic acid
b. benzaldehyde
c. HOAc
d. acetaldehyde
e. 1-hydroxy-1-phenylethane
235. Condensation Reaction. diethyl adipate + sodium ethoxide →
a. 2-carboethoxycyclopentanone
b. cyclohexanone
c. sodium adipate
d. ethyl hexanoate
e. no reaction
236. Discriminating Reagent. benzoic acid and acrylic acid →
a. p-hydroxyaniline
b. thionyl chloride
c. bromine in carbon tetrachloride
d. Lucas reagent
e. aqueous potassium hydroxide

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237. β-hydroxy Ester Synthesis. ethyl bromacetate + zinc + 2-butanone →


a. 2-butanol
b. ethyl-3-hexenoate
c. ethyl-3-methyl-3-hydroxypentanoate
d. 5-methyl-4-hepten-3-one
e. ethyl acetate

238. Reduction of Nitriles. proprionitrile + lithium aluminum hydride →


a. n-butylamine
b. n-butyramide
c. butane
d. butyric acid
e. n-propylamine
239. Reducing Power. Lithium aluminum hydride is useful for the reduction of
a. aldehydes
b. esters
c. carboxylic acids
d. nitriles
e. all of the above
240. Reactions of Amides. Heating an amide with phosphorus pentoxide results in
a. liberation of the free amine
b. formation of a phosphoramide
c. liberation of the free carboxylic acid
d. reduction
e. formation of a nitrile

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241. Cross Claisen Condensation. + in the presence of NaOCH3

a.

b.

c.
d. Reaction not possible
e. None of the above
242. Saponification. Which of the following statement regarding saponification is true?
a. Glyceraldehyde is produced as a by-product of soap in the process.
b. A mole of NaOH can saponify fatty acids.
c. Soaps are saponifized from triacyl glyceryl alkanoate.
d. All are true.
e. All are false.
243. Molecular Geometry. Which is trigonal?

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a. B(CH3)3 b. Methyl Anion c. N(CH3)3 d. Amide Ion e. All of the above


244. Rate of Halogenation. Predict the proportion of isomeric products from chlorination of isobutene.
a. 64% 10; 36% 30 b. 36% 10; 64% 30 c. 25% 10; 35% 20, 40% 30 d. 64% 10; 36% 20 e. 100% 30

245. Structural Isomers. What alkane or alkanes of molecular weight 86 have two monochloro derivatives?
a. 2,3-dimethylbutane
b. n-hexane
c. 2,2-dimethylbutane
d. 2,3-dimethylpropane
e. None of the above
246. Structural Isomers. How many tri-chloroderivatives are possible for cyclopentane?
a. 4 b. 5 c. 8 d. 3 e. 2
247. Ease of Abstraction. Arrange the following types of hydrogen according to increasing ease of abstraction
A. vinylic B. allylic C. tertiary
a. B<A<C b. A<C<B c. C<A<B d. A<B<C e. A=B=C
248. Chirality of Molecules. Which of the following compounds is achiral?
a. 1-chloro-2-bromobutane
b. 2-chloro-2-methylpentane
c. 3-chloro-2-methylpentane
d. 4-chloro-2-methylpentane
e. All are chiral.
249. Chirality of Molecules. What is (are) the lowest molecular weight alkane that is (are) chiral?
a. 3-methylpentane
b. 3-methylhexane
c. 2,2-dimethylpentane
d. isopentane
e. A,C and D
250. Dipole Moment. Which must be the dipole moment of the anti-conformation of 1,2-dichloroethane?
a. greater than zero

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b. zero
c. less than zero
d. infinity
e. undefined
251. Structural Isomers. Neglecting enantiomers, how many isomers are possible for C3H5Cl?
a. 3 b. 4 c. 5 d. 2 e. 6

252. Dehydrohalogenation of Alkyl Halides. What alkyl halide (if any) would yield 2-pentene upon dehydrohalogenation?
a. 2-pentylchloride
b. 1-pentylchloride
c. 3-pentylchloride
d. All of the above
e. None of the above
253. Trans versus Cis-Alkenes. The compound cis-3-hexene will differ from trans-3-hexene in the following properties except
a. dipole moment
b. infrared spectrum
c. product of hydrogenation
d. rate of hydrogenation
e. the compounds have similar properties on the aspects mentioned above
254. Dehydrohalogenation of Alkyl Halides. The major expected from the dehydrohalogenation of 2-bromohexane is
a. Z-2-hexene b. 1-hexene c. E-2-hexene d. All of the above e. None of the above
255. Dehydration of Alcohols. When neopentyl alcohol is heated with acid, it is slowly converted into an 85:15 mixture of two alkenes
with five carbon atoms. The major component of the product mixture is
a. cyclopentane
b. CH2=CH(C3H7)
c. (CH3)2C=CHCH3
d. CH2=C(CH3)C2H5
e. None of the above
256. Hydrohalogenation of Alkenes. The product expected from the reaction of isobutylene with Br2, H2O
a. 1,2-dibromobutane
b. 2,3-dibromobutane
c. 2-bromo-2-methyl-1-propanol

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d. 1-bromo-2-methyl-2-propanol
e. None of the above

Method of Organic Detection. For numbers 173-176, assume the choices to be limited to the following
a. alkane
b. 30 alcohol
c. alkyl halide
d. alkene
e. none of the above
257. Insoluble to sulfuric acid.
258. Insoluble to sulfuric acid, Br2/CCl4, potassium permanganate, and CrO3/AgNO3
259. Insoluble to CrO3/AgNO3
260. Soluble to sulfuric acid and Br2/CCl4.
261. Ozonolysis of Dienes. The name of the alkene that would yield on ozonolysis CH3CHO, HCHO, OHCCH2CHO
a. 2-ethyl-2-pentene
b. 1,3-hexadiene
c. 4-methyl-1,3-pentadiene
d. 1,4-hexadiene
e. None of the above
262. Stereochemistry. Which of the following statements is false?
a. Synthesis of chiral compounds from achiral reactants always yields the racemic modification.
b. Optically inactive reactants yield optically inactive products.
c. A racemic mixture is converted by an optically active reagent into a mixture of diastereomers which can then be separated.
d. A stereospecific reaction yields predominantly one stereoisomer of several diasteroemeric possibilities.
263. Grignard Reaction. When 1-hexyne was added to a solution of n-propylmagnesium bromide, a gas was evolved. What gas is it?
a. hydrogen
b. water vapor

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c. bromine
d. propane
e. methane

264. Hydration of Alkyne. Hydration of propyne yields


a. acetone
b. propanone
c. 2-propanol
d. all of the above
e. no reaction
265. Reactions of Cycloalkenes. Name the principal organic product expected from the reaction: cyclopentene + CHCl3 + t-BuOK
a. 6,6-dichlorobicyclo[3.1.0]hexane
b. cyclohexene
c. bicycle[3.1.0]hexane
d. 1,2-dichlorocyclohexene
e. No reaction
266. Electrophilic Aromatic Substitution. Which of the following reacts fastest toward ring nitration?
a. aniline
b. acetanilide
c. acetophenone
d. benzyl
e. benzyl chloride
267. Base Hydrolysis of Fatty Acids. Base hydrolysis of Tristearin yields
a. Glycerol
b. Stearic Acid
c. Stearol
d. Glycine
e. None of the above
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268. Reactions of Anhydride. Reaction of benzoic anhydride with aniline yields


a. N-phenyl benzamide
b. N,N-dimethyl aniline
c. benzoyl chloride
d. sodium benzoate
e. no reaction

269. Synthesis of Carboxylic Acids. The needed reagent to synthesize benzoic acid from acetophenone
a. aq. HCl
b. Br2, NaOH
c. NH2NH2, NaOH
d. KMnO4
e. mCPBA
270. Synthesis of Amines. n-pentylamine may be synthesized from an alcohol using the process of
a. Hofmann degradation
b. nitrile reduction
c. reductive amination
d. all of the above
e. none of the above
271. Basicity of Organic Compounds. Choose the most basic compound from each set.
A. a. Ammonia; b. Aniline, c. Cyclohexylamine
B. d. Ethylamine; e. 2-aminoethanol; f. 3-amino-1-propanol
C. g. Aniline; h. p-methoxyaniline; i. p-nitroaniline
a. afh
b. cdh
c. cdg
d. adh
e. adg
272. Halogenation of Alkenes. Name the product formed from the reaction of 1-phenylpropene with (1) excess Br2/CCl4 and then (2)
KOH, alcohol
a. 1-phenylpropyne

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b. p-bromophenylpropane
c. 1-bromophenylpropane
d. p-bromophenylbenzene
e. none of the above

273. Halogenation of Alkenes. What final monobromination product(s) would abstraction of the most reactive kind of hydrogen in 1-
phenyl-2-hexene leads to?
a. C6H5CHBrCH=CHCH2CH2CH3
b. C6H5CH2CBr=CHCH2CH2CH3
c. (C6H4Br)CH2CH=CHCH2CH2CH3
d. C6H5CH2CH=C(Br)CH2CH2CH3
e. Both a and b
274. Organometallic Reactions of Alkyl Halides. Name the chief organic product expected from the reaction (if any) of n-butyl
bromide with Li, then CuI, ethyl bromide.
a. n-hexane
b. 1-butene
c. 1-butyne
d. none of the above
e. no reaction
275. Synthesis of Alkynes. 2-Heptyne is obtained when n-butyl bromide is reacted with
a. Na + propyne
b. ethylene
c. Na in liquid NH3
d. acetic anhydride
e. none of the above
276. Molecular Orbitals of Conjugated Systems. The pi-electron of a allyl anion system in the ground state
a. has a bonding HOMO
b. is paramagnetic
c. has an antibonding LUMO

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d. has two electrons


e. all of the above
277. Electrocyclic Reactions. Which is forbidden?
a. [2+2], thermal
b. [2+4], thermal
c. [2+2], photochemical
d. all are forbidden
e. none are forbidden
For the next few numbers labelled with Discriminating Reagents, determine which reagent(s) would serve to distinguish between them
278. Discriminating Reagents. proprionic acid and methyl acetate
a. aq. NaHCO3
b. aq. NaOH
c. Grignard Reagent
d. CrO3, H2SO4
e. none of the above
279. Discriminating Reagents. n-butyryl chloride and n-butyl chloride
a. aq. NaHCO3
b. Lucas Reagent
c. Fehling’s Reagent
d. H2SO4
e. none of the above
280. Discriminating Reagents. glyceryl tristearate and glyceryl tridleate
a. Br2/CCl4
b. HCHO, formic acid
c. Li, CuI
d. excess CH3I
e. none of the above
281. Discriminating Reagents. p-nitrobenzamide and ethyl-p-nitrobenzoate
a. I2, NaOH
b. aq. NaOH
c. NH2NH2, NaOH

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d. all of the above


e. none of the above
282. Discriminating Reagents. benzonitrile and nitrobenzene
a. NaOH
b. H2, PtO2
c. Na metal
d. NH3
e. none of the above
283. Discriminating Reagents. acetic anhydride and n-butyl alcohol
a. aq. NaHCO3
b. KMnO4
c. sodium bisulfite
d. AgNO3
e. none of the above
284. Discriminating Reagents. glyceryl monopalmitate and glyceryl tripalmitate
a. CrO3/H2SO4
b. NaOH
c. cold dilute KMnO4
d. Na(Hg), in HCl
e. none of the above
285. Discriminating Reagents. ammonium benzoate and benzamide
a. cold aq. NaOH
b. aq. NaOH, heat
c. KMnO4
d. aq. HCl
e. none of the above
286. Discriminating Reagents. aniline and cyclohexylamine
a. Br2, CCl4
b. aq. Br2
c. HCl
d. KMnO4
e. none of the above

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287. Discriminating Reagents. m-nitrotoluene and phenylnitromethane


a. NaOH
b. H2SO4
c. Br2, CCl4
d. KMnO4
e. none of the above

For the next few numbers labelled with Converting Reagents, choose the best set of reagents which accomplishes the desired conversion
288. Converting Reagents. N-N-dimethylcyclohexylamine → cyclohexene
a. P2O5
b. H2O, heat
c. NaOH, I2
d. CH3I, Ag2O, heat
e. none of the above
289. Converting Reagents. hexose → pentose
a. CH3OH, H2SO4/(CH3O)2SO2
b. Br2, H2O/CaCO3, Fe3+, H2O2/aq. acid, heat
c. NaCN/aq. acid, heat/ Na(Hg)
d. NaNO2, H2SO4/H3PO2, H2O
e. None of the above
290. Converting Reagents. 4-methylpentanoic acid → leucine
a. thionyl chloride followed by excess ammonia
b. bromine, phosphorus tribromide followed by excess ammonia
c. sodium amine
d. sodium hydroxide followed by CH3NH2Cl
e. none of the above
291. Converting Reagents. cyclohexanone → butanedicarboxylic acid
a. hot acidic potassium permanganate
b. O3, Zn, H2O
c. LiAlH4/H2SO4, heat/KMnO4

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d. Potassium Phthalimide/ aq. acid, heat


e. none of the above
292. Converting Reagents. ethyl benzoate → benzamide
a. HCl/PCl5/NH3
b. HNO3, H2SO4/Sn, HCl
c. KMnO4/SOCl2/NH3
d. H2SO4/NH3
e. none of the above
293. Converting Reagents. toluene → methylbenzyl amine
a. H2SO4,HNO3/H2, Pd
b. H2SO4, HNO3/Sn, HCl/HONO, Cu2(CN)2, LiAlH4
c. H2SO4, HNO3/KMnO4/SOCl2/NH3
d. H2SO4, HNO3/NaBH4, acid/methyl amine
e. none of the above
294. Converting Reagents. cyclopentyl bromide → methyl cyclopentyl ketone
a. sodium methoxide, formaldehyde
b. KOH, EtOH/KMnO4
c. Mg, Et2O/CdCl2/CH3COCl
d. methanol, Na/CrO3, acid
e. none of the above
295. Converting Reagents. cyclohexene → 2,6-octadiene
a. KMnO4/H2, Pd/acid, heat
b. O3/CH3MgBr/H2O/acid, heat
c. Br2, NaOH/KMnO4/LiAlH4
d. heat
e. none of the above
296. Converting Reagents. benzyl bromide → benzyl amine
a. excess NH3
b. NaNH2, EtOH
c. potassium phthalimide, NaOH, water
d. sodium cyanide, lithium aluminum hydride
e. none of the above

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297. Converting Reagents. 2-butanone → 2-methyl-1-butene


a. formaldehyde
b. NaOCH3
c. methylenetriphenylphosphine
d. methylene triplet
e. none of the above

298. Combustion. On combustion, 2.69 mg of an organic compound, CxHyOz, gives 5.20 mg CO2 and 3.20 mg H2O. The compound is
known to have a molecular weight of about 45 g/mole. What is its molecular formula?
a. C2H6O
b. C3H6O
c. C4H8O
d. C3H6O
e. none of the above
299. Stepwise Synthesis. A hydrocarbon, A, adds one mole of hydrogen in the presence of platinum catalyst to form n-hexane. When
A is oxidized vigorously with KMnO4, a single carboxylic acid, containing three carbon atoms, is isolated. Give the name of A.
a. 2-hexene
b. 1-hexene
c. cyclohexene
d. 3-hexene
e. none of the above
300. Stepwise Synthesis. A chemist added water and acid to an unknown ester of formula C6H12O2 to produce an acid X and an alcohol
Y. Oxidation of Y with chromic acid produce X. What was the original ester?
a. propyl propanoate
b. ethyl butanoate
c. propanoic anhydride
d. propyl acetate
e. none of the above
301. Stepwise Synthesis. Hydrolysis of a neutral compound A, C5H10O2, gave an acid B and an alcohol C. C reacted with PCl3, and was
then treated with Mg. Addition of CO2 followed by hydrolysis yielded an acid identical to B. What is compound A?
a. ethyl propionate

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b. methyl butanoate
c. propyl acetate
d. pentanal
e. none of the above

302. Stepwise Synthesis. Compound A, C5H10, decolorized a solution of Br2 in CCl4. When it was dissolved in cold, concentrated sulfuric
acid and then heated with water, B resulted. B, (C5H12O) reacted with chromic acid to give C (C5H10O). Both B and C gave positive
iodoform tests. The reaction mixture of iodoform tests also produced isobutyric acid. Determine the identity of A.
a. 3-methyl-2-butene
b. 3-methyl-2-butanol
c. methyl isopropyl ketone
d. 2-methyl-2-butene
e. none of the above
303. NMR. Give the name of the compound, C10H12, which is consistent with the following set of NMR data: multiplet, 0.65, 2H;
multiplet, 0.81, 2H; singlet, 1.37, 3H; and singlet, 7.17, 5H
a. phenylcyclobutane
b. propylbenzene
c. 1-methyl-1phenylcyclopropane
d. 1-phenyl-1-butyne
e. none of the above
304. IR. Compound A, C4H8O, is optically active, reacts rapidly with bromine at 00C, and absorbs strongly at 3300 cm-1 in its air spectrum.
Compound A is
a. CH3CH(OH)CH2CH3
b. H2C=CHCH(OH)CH3
c. CH3OCH2CH=CH2
d. H2C=CHCH2CH2OH
e. none of the above
305. Synthesis of Alkenes. Compound P, an alkene, is the major product of the following reactions: (2-bromobutyl)cyclohexane +
KOH, EtOH → compound P. Compound P is:
a. (2-hydroxybutyl)cyclohexane
b. butenylcyclopentane

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c. butenylcyclohexane
d. propylcyclohexane
e. none of the above

306. Solvent Extraction. Three water-insoluble liquids, aniline, n-butylbenzene and n-valeric acid and a solid, p-nitroanisole are dissolved
in ether. If the ether layer was extracted with aqueous NaOH, and the resulting aqueous layer was separated and acidified, which
compound may be obtained from this layer?
a. aniline
b. n-butylbenzene
c. n-valeric acid
d. p-nitroanisole
e. none of the above
307. Solvent Extraction. If the resulting ether in the previous number was again extracted with aqueous HCl, and the resulting aqueous
layer was again separated and made alkaline with NaOH, what is obtained?
a. aniline
b. n-butylbenzene
c. n-valeric acid
d. p-nitroanisole
e. none of the above
308. Nucleophilic Substitution Reactions. p-nitrophenol + C2H5Br + NaOH(aq) →
a. p-ethyl nitrobenzene
b. m-ethyl nitrobenzene
c. p-ethoxy nitrobenzene
d. p-nitrobenzoic acid
e. none of the above
309. Electrophilic Aromatic Substitution. p-ethoxy aniline + acetyl chloride →
a. p-ethoxy benzamide
b. N-ethoxyphenyl acetamide
c. p-ethoxy acetamide
d. no reaction
e. none of the above

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310. Hydrohalogenation of Alcohols. β-(o-hydroxyphenyl)ethyl alcohol + HBr →


a. β-(o-hydroxyphenyl)ethylene
b. benzyne
c. β-(o-hydroxyphenyl)ethyl bromide
d. no reaction
e. none of the above
311. Diazotization. acetyl chloride + diazomethane (CH2N2) →
a. acetamide
b. diazoacetone
c. acetic acid
d. chloroacetone
e. none of the above
312. Dehydration of Alcohol. tetra-n-propylammonium hydroxide + heat →
a. tri-n-propyl amine
b. ammonia
c. n-propane
d. propene
e. none of the above
313. Electrophilic Aromatic Substitution. p-toluidine + NaNO2 + HCl →
a. p-anisole
b. p-methylaniline
c. p-cresol
d. phenol
e. none of the above
314. Reactions of Alcohols. D-glucose + Br2, H2O →
a. glucitol
b. glucaric acid

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c. gluconic acid
d. dextrin
e. none of the above

315. Reactions of Fused Ring Aromatics. naphthalene + (1) H2SO4, (2) KOH, fuse, (3) H2SO4 →
a. α-naphthol
b. β-naphthol
c. α-sulfonyl naphthol
d. no reaction
e. none of the above
316. Reactions of Phenols. 5-chloro-2-methylphenol + (1) C6H5N2+, OH-, (2) SnCl2, HCl, and (3) FeCl2 →
a. 5-chloro-2-methyl benzoic acid
b. ferric 5-chloro-2-methyl phenoxide
c. 2-chloro-5-methyl parabenzoquinone
d. no reaction
e. none of the above
317. Oxidation of Fused Ring Aromatics. Oxidization of α-napthol yields
a. 1,4-binaphthol
b. 1,4-naphtoquinon
c. 1,2- naphthoquinone
d. no reaction
e. none of the above
318. Electron Affinity Trend. Which of the following elements has the highest electron affinity?
a. Phosporus
b. Sulfur
c. Chlorine
d. Helium
e. Neon
319. Volatility. The concept that best explains the greater volatility of o-nitrophenol over p-nitrophenol during steam distillation of a
mixture of the compound is
a. hyperconjugation

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b. hydrogen bonding
c. the ortho effect
d. resonance
e. symmetry
320. Organic Class. This formula represents a member of the class of compounds known as
a. terpenes
b. alkaloids
c. carbohydrates
d. steroids
e. vitamins
321. Covalent Bonds. Covalent bonds are the most likely to exist between
a. atoms of non metals
b. atoms of metals
c. an atom of a nonmetal and an atom of a metal
d. atoms of elements with great differences in electronegativity
e. atoms of elements with great differences in ionization energy
322. Organic Group Analysis. By the end of group analysis, the hydrolysis of one molecule of completely methylated amylose gives rise
a. one molecule of tetra-O-Me-D-glucose
b. one molecule of tri-O-Me-D-glucose
c. equal number of tetra-O-Me-D-glucose
d. n number of tri-O-Me-D-glucose
e. none of the above
323. Vitamins. Vitamin A serves as an antioxidant because of its
a. hydrocarbon structure
b. double bonds
c. hydroxyl end group
d. cyclohexane structure
e. all of the above
324. Fatty Acids. The major fatty acid in coconut oul is
a. Palmitic Acid
b. Lauric Acid
c. Caproic Acid

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d. Stearic Acid
e. Oleic Acid

325. Iodoform Reaction. The iodoform reaction (reagents: I2 + NaOH) may be used to distinguish between the following pairs of
compounds
a. acetoacetone and acetaldehyde
b. 1-propanal and 1-propanol
c. ethanol and propanal
d. methylethylketone and methylphenylketone
e. 2-propanol and 2-propanone
326. Reactivity of Ketones. Which of the following generally reacts with ketones to form olefins?
a. (Ar)n-P-CH2-
b. NaOC2H5
c. Ch3MgBr
d. Ar-N=C=O
e. cyclohexane-N=C=N-cyclohexane
327. Electrophilic Aromatic Substitution. The nitration of benzene does not exhibit a significant isotope effect because
a. no C-H bond is broken at the rate-determining step
b. a C-H bond is broken at the rate-determining step
c. k1=k2
d. k1>k2
e. none of the above
328. Halogenation of Alkanes. The chlorination of n-propane, in the presence of light, involves the formation of
a. alkyl free radicals
b. alkyl carbocation
c. alkyl carbanion
d. Cl+
e. Cl-
329. Bond Overlap. Which of the following compounds has a bond formed by overlap of sp2-sp3 hybrid overlaps?
a. CH3C≡CH
b. CH3CH=CHCH3

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c. HC≡CH
d. CH3CH2CH2CH3
e. CH2=CHCH=CH2

330. Dipole Moment. Which of the following compounds has the largest dipole moment?
a. CCl4
b. CO2
c. (CH3)2C=C(CH3)2
d. trans ClCH=CHCl
e. cis ClCH=CHCl
331. Dehydrohalogenation via E1 Mechanism. Which of the following compounds undergoes dehydrohalogenation most rapidly in
boiling ethanol by an E1 mechanism?
a. CH3CBr=C(CH3)2
b. CH3CHBrCH(CH3)2
c. Φ-CHBrCH3
d. (para) O2N-Φ-CHBrCH3
e. (para) CH3O-Φ-CHBrCH3
332. Tautomerization. Which of the following compounds does not show tautemerism?

a.

b.

c.

d.

e.
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333. Acceleration of Reactions. The addition of traces of benzoylperoxide at 800C may be expected to accelerate all of the following
reactions except
a. isopropylbenzene oxidized to (CH3)2(HOO-C)-phenyl
b. toluene + NBS → phenylbromide
c. cyclohexene + HBr → bromocyclohexane
d. (CH3)3CH + Br2 → (CH3)3CBr + HBr
e. CH3CH2CH2COOH → CH3CH2CH3 + CO2
334. Energy of Activation. The energy of activation in a one-step reaction
a. is the difference between energy levels of the reactants and the final products
b. is the difference between the energy levels of the reactants and the transition state
c. varies with the concentration of the substrate
d. is the difference between energy levels of intermediate product(s) and the final products
e. none of the above
335. Bimolecular Nucleophilic Substitution Reactions. Which of the following halides generally undergoes bimolecular nucleophilic
(SN2) reactions most readily?
a. tert-butylbromide
b. phenyl bromide
c. 1-bromobicyclo[2.2.1]heptane
d. bromopropene
e. benzyl bromide

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336. Aromaticity. Which of the following molecules is not considered aromatic?

a.

b.

c.

d.

e.

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337. Diels-Alder Reaction. The dimer formed by heating 1,3-butadiene has which of the following structures?

a.

b.

c.

d.

e.
338. Hydrohalogenation of Akenes. The hydrohalogenation of 1-phenyl-1-propene using HBr is
a. 1-phenyl-2-bromopropane
b. 1-(p-bromophenyl)propane
c. 1-phenyl-1-bromopropane
d. o-bromopropylbenzene
e. none of these
339. Boiling Point Comparison. Which of the following has the lowest boiling point.
a. α-hydroxynitrobenzene
b. m-hydroxynitrobenzene
c. p-hydroxynitrobenzene
d. p-methoxynitrobenzenyl chloride
e. none of the above

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340. Alcohols. Alcohols are


a. the products of the reduction of aldehydes and ketones
b. prepared from the dehydration of aldols
c. more acidic than phenol
d. all of the above
e. none of the above
341. Ozonolysis. Ozonolysis of a symmetrical alkene yields
a. a ketone
b. two mole of aldehydes or ketones for every mole of the alkene
c. one mole of aldehyde and a mole of a short chain alcohol per one mole of alkene
d. two moles of carboxylic acids per mole alkene
e. none of the above
342. Stability. The stability of benzoate anions is due to
a. (−) resonance effect
b. (+) resonance effect
c. (+) inductive effect
d. (−) inductive effect
e. none of the above
343. Reducing Agents. All can reduce oximes to amines except
a. H2, Ni
b. (1) Zn, HCl (2) OH-
c. NH4SH
d. LiAlH4
e. All can reduce oximes to amines
344. Reducing Agents. Lithium aluminum hydride can reduce all except
a. nitroso compounds
b. nitriles
c. olefins

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d. amides
e. enones

345. Synthesis of Amines. Which of the following statements about methods of amine synthesis is false?
a. A ketone undergoing a reductive amination will yield an imine as a transition state and a primary amine as a product.
b. A primary amine can be dimethylated using formic acid and formaldehyde.
c. Hoffman elimination converts an amide to an amine using Br2, OH.
d. Excess alkyl halide in the reaction RX + ammonia → RNH2 increases the chances of multiple alkylation in the N atom.
e. In forming primary amine, Gabriel Synthesis is more advisable because of the use of phthalimide ion which avoids
unnecessary complications.
346. Hoffman Degradation. The following statement is true regarding Hoffman degradation except
a. Using Br2, KOH, an amide is converted to an amine with K2CO3, KBr and water as by-products.
b. An acylnitrile TS is formed when the base abstracts the H atom of the nitrogen.
c. An acylnitrile TS stabilizes to an isocyanate compound upon rearrangement.
d. All are true.
e. All are false.
347. Gabriel Synthesis. Which of the following statement regarding Gabriel Synthesis is true?
a. An SN2 reaction happened between phthalimide anion and alkyl halide.
b. 2 moles of KOH and H2O frees the amine immediately from the ring cage and oxidizes the carbonyl to carboxylate, forming
1,2-dicarboxylatecyclohexane.
c. Hydrazine refluxed with ethanol opens the cage but does not immediately free the amine.
d. All are true.
e. All are false.
348. Boiling Point Comparison. Which of the following has the highest boiling point?
a. propyl amine
b. N,N,N-triethylamine
c. N,N-ethylmethylamine
d. N,N,N-chlorodimethylamine
e. 1-bromopropyl amine

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349. Solubility Comparison. Given the following set of compounds, which is true regarding their solubility in water?
A. N,N-ethylmethylamine B. N,N,N-trimethylamine C. N,N,N-trimethylammonium chloride
a. A>B>C
b. C>B>A
c. A>C>B
d. C>A>B
e. B>C>A
350. From Ketone to Amine. 2-butanone → 2-butylamine
a. (1) ammonia (2) H2, Pd
b. NaNH2
c. (1) NaHSO4 (2) NH3
d. LiAlH4
e. Br2, KOH
351. Reduction of Nitriles. propyl nitrile + LiAlH4 →
a. n-propylamine
b. n-butyramide
c. n-butylamine
d. 2-butylamine
e. none of the above
352. From Carboxylic Acid to Amine. butyric acid → n-propylamine
a. (1) thionyl chloride, (2) sodium amide
b. (1) bromine, (2) potassium phthalimide (3) aqueous acid
c. (1) thionyl chloride (2) ammonia (3) bromine, aqueous NaOh
d. All can reduce the acid to an amine
e. None of the above
353. From Alkyl Halide to Amine. 1-bromobutane → n-butylamine
a. sodium amide

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b. (1) potassium phthalimide (2) NaOH, water


c. (1) sodium cyanide, (2) lithium aluminum hydride
d. All can reduce an alkyl halide to amine
e. None of the above

354. Salt Formation. Which of the following amines cannot form halide salts?
a. ethylamine
b. N,N-diethylamine
c. N,N,N-triethylamine
d. quarternary ethylammonium bromide
e. quarternary ethylammonium hydroxide
355. Basicity of Amines. Which of the following statement regarding basicities of amines is true?
a. Aniline is more basic than 20 alkyl amine because of resonance.
b. In aqueous solution, 30 amines are more basic than 20 amines.
c. Primary amines are more basic than ammonia in aqueous solution.
d. All are false.
e. All are true.
356. Hoffman Degradation. Which of the following statement about Hoffman Degradation is false?
a. Hoffman degradation yields alkenes which do not follow Zaitsev Rule.
b. Only quarternary ammonium hydroxide can undergo this method of degradation.
c. Hoffman degradation uses Br2, KOH to degrade amines to less substituted alkenes.
d. The TS is more carbanionic in nature.
e. Heat is applied to push an elimination reaction.
357. Reaction of Amines with HONO. Which of the following statement regarding amine’s reaction to HONO is true?
a. Primary amines produce nitroso compounds when reacted with HONO.
b. Secondary amines produce nitroso ammonium compounds when reacted with HONO.
c. Tertiary amines produce diazo compounds when reacted with HONO.
d. The reaction requires relatively low temperature.
e. All are true.
358. Hinsberg’s Test. What type of amine exhibits no reaction with Hinsberg’s reagent and KOH but produces a clear solution when
reacted with dilute HCl?
a. primary

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b. secondary
c. tertiary
d. quarternary
e. all can be

359. Oxidation of Amines. Which of the following is true about amine oxidation?
a. Primary amines are oxidized to hydroxylamine with 1 mole of peroxide.
b. Secondary amines are oxidized to hydroxylamine with 1 mole of peroxide.
c. Tertiary amines are oxidized to N-oxides with 1 mole of peroxide.
d. Primary amines are oxidized to nitroso compounds with 2 moles of peroxide.
e. All are true.
360. Cope Elimination. N,N,N-dimethyl-2-butylamine + (1) H2O2 + (2) ∆ →

a. d. 2-butene

b. e. 1-butene

c.
361. Elimination Reaction. cyclohexylamine → cyclohexene
a. KOH, heat

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b. (1) x’s CH3I, (2) Ag2O, heat


c. sulfuric acid, heat
d. none of the above
e. not a possible reaction

362. Electrophilic Aromatic Substitution on Fused Rings. α-napthyl amine + (1) sulfuric acid, nitric acid (2) CuBr →
a. α-napthyl sulfate
b. α-napthyl bromide
c. naphthalene
d. β-naphthyl sulfate
e. none of the above
363. HONO Plus Tertiary Aromatic Amine. N,N,N-diethylphenylamine + HONO →
a. N,N,N-diethyl(4-nitrophenyl)amine
b. methyl phenyl nitroso compound
c. benzyl diazonium sulfate salt
d. none of the above
e. no reaction
364. Dimethylation of Primary Amine. Aniline → N,N,N-dimethylphenylamine
a. methyl iodide, heat
b. (1) formaldehyde (2) formic acid
c. (1) methanol, thionyl chloride, (2) water
d. none of the above
e. no reaction
365. Differentiating Reagent. aniline and N-methyl aniline
a. Peroxide
b. (1) Benzene Sulfonyl Chloride (2) KOH (3) dilute HCl
c. Acetyl Chloride
d. Ag2O, heat
e. None of the above
366. Boiling Point Comparison. Which of the following has the lowest boiling point?
a. propanoic acid
b. propanoyl amide

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c. nitropropane
d. propanol
e. propanoyl chloride

367. Synthesis of Nitro Compounds. The following are reactions that can synthesize –NO2 compounds except
a. reaction of alkyl halide and nitro anion via SN2
b. reaction of alkane with nitric acid at 4000C via free radical substitution
c. reaction of benzene with nitric acid and sulfuric acid via EArS
d. reaction of alkyl halide and nitro anion via SN1
e. All can synthesize nitro compounds
368. Reduction of Nitro Compounds. Which of the following statements is false regarding reduction of nitro compounds?
a. Lithium aluminum hydride can reduce nitro compounds to amines.
b. Tin or Fe with HCl can reduce nitro compounds to amines.
c. Hydrogen with Pd reduces everything but leaves NO2 untouched.
d. All are true.
e. All are false.
369. Knocvenegel Condensation. benzaldehyde + CH3NO2 in KOH →
a. (Ph)CHOHCH2NH2
b. Ph(C=O)O(N=O)CH3
c. Ph-CH=CH2
d. Ph-CH=CHNO2
e. None of the above
370. Heterocyclic Compounds. Which of the following compounds is not heterocyclic?
a. pyrrole
b. furan
c. thiopene
d. pyridine
e. all are heterocyclic
371. Physical Properties of Five-Membered Heterocyclic Rings. Which of the following statements about five-membered
heterocyclic rings is true?
a. Pyrrole has a larger net dipole moment than furan.

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b. Furan and pyrrole has net dipole moments pointing toward the electronegative atoms O and N.
c. Thiopene has a larger net dipole moment than pyrrole because of its electronegative atom S.
d. All are true.
e. All are false.

372. Basicity of Pyrrole. Which of the following statement regarding basicity of pyrrole is true?
a. Pyrrole is more basic than furan because of its aromaticity.
b. Furan is more basic than pyrrole because of its aromaticity.
c. Pyrrole is less basic than furan because of its aromaticity.
d. Furan is less basic than pyrrole because of its aromaticity.
e. None are true.
373. Chemical Properties of Heterocyclic Compounds. Which of the following is true about five-membered heterocyclic
compounds?
a. furan + H2, Pt → THF
b. In terms of reactivity: pyrrole is more reactive than benzene
c. thiopene + t-butyl oxide → 2-butoxythiophene
d. all are true
e. all are false
374. Reactions of Five-Membered Heterocyclic Compounds. thiophene + benzoyl chloride, SnCl4 →

a.

b.

c.

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d. reaction not possible


e. none of the above

375. Solubility Comparison. Which of the following organic compound is the most soluble to water?
a. pyridine
b. pyrrole
c. furan
d. pyrimidine
e. thiophene
376. Reactivity of Heterocyclic Rings. Which of the following statements is true?
a. Pyrrole can be used as a nucleophilic reagent because of its lone pairs on N and can readily substitute halides on acyl halides.
b. Pyridine can be attacked at the ortho, para positions by an electrophilic reagent as substitution at these positions were
stabilized by resonance.
c. Pyrrole can be attacked by electrophilic reagents at the meta position as it is stabilized by resonance structures.
d. Pyridine can be used as a nucleophilic reagent because of its extra lone pair on N.
e. Pyridine cannot be nitrated at normal conditions because of the deactivating electronegative N atom.
377. Nitration of Pyridine. pyridine + HNO3, H2SO4, 3500C →
a. 2-nitropyridine
b. 3-nitropyridine
c. 4-nitropyridine
d. mixture of a and c
e. none of the above
378. Friedel Crafts Alkylation on Pyridine. pyridine + CH3X →
a. 2-methylpyridine
b. 3-methylpyridine
c. 4-methylpyridine
d. mixture of a and c
e. none of the above
379. NArs on Pyridine. pyridine + sodium amide, heat →

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a. 2-aminopyridine
b. 3-aminopyridine
c. 4-aminopyridine
d. mixture of a and c
e. none of the above

380. Hydrohalogenation of Heterocyclic Compounds. Hydrohalogenation of heterocyclic compounds increase


a. acidity
b. basicity
c. unsaturation
d. aromaticity
e. reactivity towards electrophilic reagents
381. EArS on Pyrimidine. 2-ethoxypyrimidine + HNO3, H2SO4, 3500C →
a. meta-ethoxynitropyrimidine
b. para-ethoxynitropyrimidine
c. Both a and b
d. None of the above
e. No reaction
382. NArS on Pyrimidine. 5-chloropyrimidine + KNH2 →
a. para-aminochloropyrimidine
b. meta-aminochloropyrimidine
c. 5-aminopyrimidine
d. both a and b
e. none of the above
383. Reactivity Towards Nucleophilic Reactions. Given the following compounds, which is true?
A. pyrimidine B. pyridine C. benzene D. pyrrole
a. A>B>C>D
b. D>C>B>A
c. A>B>D>C
d. C>D>B>A
e. D>C>A>B
384. Reactivity of Indole. The positions at which EArS and NArS primarily occur

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a. 3, 4 and 6
b. 2, 4 and 6
c. 4 and 7
d. 5 and 6
e. 2

385. Natural versus Synthetic Polymers. All are natural polymers except
a. carbohydrates
b. proteins
c. polyethylene
d. cellulose
e. all are natural
386. Nomenclature of Polymers. Name the polymer (IUPAC) -[CH2CHCl]n-.
a. poly(vinyl chloride)
b. polyvinyl chloride
c. poly(1-chloroethane)
d. polychloroethane
e. none of the above
387. Classification of Polymers. PVC is an example of
a. homopolymer
b. heteropolymer
c. copolymer
d. network polymer
e. step ladder polymer
388. Physico-Chemical Properties of Polymers. Which of the following statement is true?
a. Nylon and polyurethanes held by H-bonds are usually linear and are examples of thermosets.0
b. Polypropylene, with powerful H-bonding between monomers, fit together in an isotactic manner and maintains alignment
over an increase in T.
c. Phenol formaldehydes form network or cross-linked polymers which form rigid 3D structures but are still weak to resist
increase in temperature, classifying them as thermoplastics
d. Thermosets, once heated, melts and softens and can be molded to other shapes.
e. None of these statements is true.

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389. Preparation of Polymers. Which of the following statement about polymer preparation is true?
a. Chain growth polymerization is slower than the step growth polymerization since only one chain is involved in polymer
synthesis.
b. In a chain reaction, the reactive center can be a radical, an anion or a cation.
c. Cross links are more likely to form via addition polymerization.
d. All are true.
e. All are false.
390. Polymeric Chemical Reactions. The following are polymeric chemical reactions except
a. Inhibition
b. Chain Transfer
c. Vulcanization
d. Initiation
e. Acceleration
391. Thermosets versus Thermoplastics. The following are example of thermoplastics except
a. PVC
b. Nylon
c. Polystyrene
d. Rubber
e. Polyesters
392. Polymerization. The following would result to a polymer except
a. CNCH=CH2 + KNH2 →
b. phenol + HCHO, H+ →
c. methylpropoxide + KOH →
d. all would yield a polymer
e. none would yield a polymer
393. Basicity. Aniline is more basic than
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a. p-methylaniline
b. pyrrole
c. n-methylaniline
d. diethylamine
e. ammonia

394. Basicity. Given the N atoms of histamine, which of the following statement regarding basicity is true?
a. a>b>c
b. c>b>a
c. c>a>b
d. b>a>c
e. a>c>b
395. EArS on Substituted Pyridines. 2-aminopyridine can be nitrated or sulfonated unde much milder conditions than pyridine itself;
substitution occurs chiefly at which position?
a. 1
b. 3
c. 4
d. 5
e. 6
396. Nitrosation of Amines. Nitrosation of alkul amines results in the generation of
a. carboctions
b. alkyl diazonium species as stable entities
c. alkylazo compounds
d. alkyl nitrites
e. amides with carboxylic acids
397. Pyrrole. If the nitrogen of pyrrole is protonated, the ring is
a. cleaved
b. no longer aromatic
c. susceptible to electrophilic substitution
d. expanded
e. unaffected

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398. What Reaction. N,N-dimethylcyclohexamine + (1) methyl iodide (2) Ag2O, heat →

a.

b.

c.

d.

e.

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399. Osazone and Derivative. + HCl, EtOH →


a. 2-methylcyclohexanone
b. methylphenylketone
c. benzaldehyde
d. no reaction
e. none of the above

400. Carbohydrates. The following statements about carbohydrates are true except
a. A carbohydrate is defined as a substance that yields polyhydroxy ketone (ketoses) or polyhydroxy aldehydes (aldoses) upon
hydrolysis.
b. Oligosaccharides are sugars which yield ~ten or more units of monosaccharides upon hydrolysis.
c. Lactose, maltose and cellobiose are examples of disaccharides.
d. Starch, cellulose and dextrins are examples of polysaccharides.
e. All are true.
401. Fischer’s Structure. Which of the following is the Fischer’s Structure for glucose?

a. d.

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b. e.
c. None of the above

402. IUPAC Name of Sugars. The IUPAC name for the Fischer projection of D-(+)-Glucose is
a. (2S, 3R, 4S, 5S)-2,3,4,5,6-pentahydroxyhexanal
b. (2R, 3S, 4R, 5R)- 2,3,4,5,6-pentahydroxyhexanal
c. (2S, 3R, 4S, 5S)-2,3,4,5,6-acetopentahexanol
d. (2R, 3S, 4R, 5R)- 2,3,4,5,6-acetopentalhexanol
e. none of the above
403. Haworth’s Formula. Which of the following statements regarding cyclic aldoses and cyclic ketoses are true?
a. α and β-D-(+)-glucopyranose are anomers.
b. α and β-D-(+)-glucopyranose are diastereomers.
c. α and β-D-(+)-glucopyranose are cyclic hemiacetals of glucose in chair conformation.
d. a and c are true.
e. All are true.
404. Chemical Properties of Sugars. The following are true about sugars except
a. Mutarotation is possible because there is an equilibrium between the Fischer and Haworth’s formulae.
b. The equilibrium optical rotation of sugars at aqueous solution is the average of the rotation of α and β anomers.
c. The methyl substituent in the first C of an α anomer is in the equatorial position.
d. Mutarotations only occur in basic solutions.

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e. All are true.


405. Killiani Fischer Synthesis. D-(-)-arabinose + (1) HCN, (2) Ba(OH)2, (3) H3O+, (4) Na (Hg) at pH = 3.5 →
a. D-(+)-allose
b. D-(+)-altrose
c. D-(+)-glucose
d. D-(+)-mannose
e. D-(-)-gulose
406. Glycoside Formation. Methyl-β-D-glucopyranoside + NaOH + water →
a. methanol + D-(+)-glucose
b. methyl-α-D-glucopyranoside
c. methanol + D-(+)-mannose
d. mixture of a and c
e. no reaction
407. Oxidation of Sugars. Which of the following statements about oxidation of sugars is true?
a. Benedict’s reagent uses cupric tartrate complex which is reduced to Cu2O when reacted with sugars.
b. A brick red positive result is expected when sugars are made to react with Tollen’s reagent.
c. Benedict’s and Tollen’s test give false positive results to α-hydroxyketones.
d. Benedict’s test converts the sugar to an aldaric acid.
e. Nitric acid oxidizes aldoses to aldonic acids.
408. Bromine Water. Which of the following statement about Bromine Water oxidation is true?
a. Aldoses are oxidized to aldaric acids.
b. Bromine water reacts faster with β-anomer.
c. Aldaric acids tautomerizes to either δ-lactones and γ-lactones.
d. The reaction occurs at basic pH.
e. None of the above is true.
409. Periodate Oxidation. Glucose + HIO4 →
a. Gluconic acid
b. Glucaric acid
c. Formic acid and Formaldehyde
d. All of the above may be the products of the oxidation.
e. None of the above
410. Other Reactions of Sugars. The following reactions about sugars are true except

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a. NaBH4 can reduce D-(+)-Glucose to D-(+)-Glucitol


b. The reaction of alcohol with acetone and HClO4 or pyridine protects the –OH group by acetylation
c. The reaction of alcohol with (1) acetone in sulfuric acid and (2) ammonia protects the –OH group by acetonation
d. D-fructose and D-mannose produce different osazones when reacted with excess phenylhydrazine.
e. Ruff’s Degradation shortens the sugar by one carbon using (1) bromine water, (2) CaCO3 and (3) peroxide and ferric sulfate
411. Reducing Sugars. A reducing sugar is the one that acts with
a. Fehling’s solution
b. Iodoform
c. Hydrogen Peroxide
d. Both a and b
e. a, b and c

412. Phenylosazones. D-glucose + excess phenyl hydrazine →


a. D-glucose phenylhydrazine
b. D-galactose osazone
c. D-fructose
d. Both b and c
e. None of the above
413. Stereoisomers. How many stereoisomers are there for six carbon sugars?
a. 4 b. 8 c. 16 d. 32 e. 64
414. End Group Interchange. Terminal group exchange in D-mannose will give
a. an enantiomer
b. the same aldohexose
c. a new aldohexose
d. a diasteromer
e. lactones
415. Disaccharides. Which of the following statements regarding common disaccharides is false?
a. Hydrolysis of maltose yields two moles of D-(+)-glucose.
b. The IUPAC name of sucrose is α-D-glucopyranosyl-β-D-fructofuranoside.

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c. Sucrose gives negative results to Benedict’s and Tollen’s reagent.


d. Maltose and sucrose are hydrolyzed by α-glucosidase.
e. Sucrose doesn’t react with phenylhydrazine to form osazones.
416. Polysaccharides. Which of the following statements regarding common polysaccharides is true?
a. Amylose is an unbranced polymer of D-glucose with α, 1-4 glycosidic linkages.
b. Starch is composed of 10-20 % amylose and 80-90 % amylopectin.
c. Amylopectin assumes a helical formation which assumes a compact shape of around 150,000 to 600,000 MW units.
d. Cellulose is a D-glucose pyranoside polymer linked linearly in a β 1,4 glycosidic linkage.
e. All are true.
417. Sucrose. Sucrose contains ____ chiral centers.
a. 10 b. 9 c. 12 d. 11 e. 8
418. Stereochemistry of Amino Acids. The following amino acids are optically active except
a. Alanine b. Valine c. Glycine d. Isoleucine e. Threonine
419. Basic Amino Acids. All are diamino carboxylic acids except
a. Arg b. Hyl c. Cys d. Lys e. All are diamino carboxylic
420. Zwitter Ions. The following statements about zwitter ions is true except
a. Solid zwitter ions have high melting points and are soluble in polar solvents
b. Cationic forms H3N+RCHCOOH predominates in strongly acidic solution
c. The concentration of anions and cations are equal at the isoelectric point
d. A monoamino monocarboxylic acid H3N+CHRCOO- is more acidic than somehow more basic.
e. The solubility of zwitter ions increases at the isoelectric point
421. Synthesis of Amino Acids. The following methods can be used to synthesize amino acids except
a. Ammination of α-halo acids
b. Hell-Volhard-Zelinsky Reaction with excess Ammonia
c. Malonic Ester Synthesis with excess Ammonia
d. Gabriel Synthesis using α-halo esters
e. All can be used to synthesize amino acids
422. Strecker Synthesis. 2-propanal + ammonia + HCN →
a. isoleucine
b. valine
c. threonine
d. serine

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e. none of the above


423. Reactions of Amino Acids. The following are plausible reactions of amino acids except
a. Formation of ammonium salts when reacted with aqueous HCl
b. Formation of esters when reacted with acyl halide and aqueous base
c. Formation of carboxylate salts when reacted with aqueous NaOH
d. a and c
e. All are not possible
424. Reactions of Amino Acids. Alanine + NaNO2, HCl →
a. 2-hydroxypropanoic acid
b. 3-hydroxypropanoic acid
c. α-chloropropanoic acid
d. β-chloropropanoic acid
e. Both a and c

425. Polypeptides. The following statements about proteins and polypeptides are true except
a. Peptides are amides formed by the interactions between amino groups and carboxyl groups of amino acids.
b. Peptides are amines formed by the interactions between amino groups of amino acids followed by degradation of the
carboxyl groups.
c. Protein, which is ~ greater than 10 000 g/mole, is longer than a polypeptide.
d. Glycylglycylphenylalanylphenylalanylleucine is composed of 5 amino acids.
e. All are false.
426. Analysis of Peptides. The following are sequence detection methods which can be used to analyze peptides except
a. Sanger Method
b. Edman Degradation
c. Treatment of LiAlH4, followed by acid hydrolysis
d. Carboxypeptidase
e. All are methods which can be used to analyze peptides.
427. Analysis of Peptides. Which of the following statement is false?
a. 2,4-Dinitrofluorobenzene (DNFB) is used to tag the terminal amino nitrogen of a peptide via electrophilic aromatic
substitution at the fluorine atom.

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b. Once the amino acid attacks the C=S bond of phenyl isothiocyanate, the freed lone pair of the nitrogen atom will
subsequently attack the nearest carbonyl carbon (that belongs to the first amino acid), tearing the first segment from the
chain and forming a phenylhydantoin labelled amino acid.
c. Carboxypeptidase aides the cleavage of the carbonyl group and the amino group of the same amino acid.
d. All are true.
e. All are false.
428. Sequence Detection. Which of the following is the correct sequence for the reaction Ala, Arg, Cys, Val, Leu + H+, H2O →
CysArg + AlaCys + ArgVal + LeuAla
a. AlaCysArgValLeu
b. LeuArgCysAlaVal
c. AlaCysLeuArgVal
d. ValCysAlaArgLeu
e. None of the above
429. Synthesis of Peptides. Which of the following statements regarding peptide synthesis is false?
a. It is needed to block the amino group and activate the carboxylic acid group in synthesizing peptides.
b. Carbobenzoxychloride or benzyl chloroformate can be used to block the amino group of the peptides.
c. To remove the blocking reagent, H2 in Pd or HBr in cold HOAC is used because they are very selective to the blocking
reagent and does not cleave peptide bonds.
d. SOCl2 or dicyclohexylcarbodiimide is used to activate the carboxylic acid groups.
e. All statements are true.
430. Reactions of Amino Acids. glycine + benzoyl chloride + acetic anhydride →
a. n-benzoylglycine
b. n-benzoylglycinyl acetate
c. phenylalanine
d. glycyl anhydride
e. none of the above
431. Reactions of Amino Acids. alanine + DCC →
a. alanylalanine + dicyclohexylurea
b. cyclohexyl allalinate
c. n-cyclohexylalanine
d. dicyclohexyl carbonate + alanylalanine
e. polyalanine + dicyclohexyl urea

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432. Reactions of Amino Acids. alanine + 1 equiv. benzyl chloroformate


a. n-carbobenzyloxyalanine
b. alanyl carbobenzyloxyl anhydride
c. benzyl alalinate
d. benzyl chloride
e. n-benzylalanine
433. Convert your Sugar! Choose the best set of reagents and/or conditions for the conversion of D-ribose to methyl-α-D-
ribofuranoside.
a. p-toulenesulfonic acid, methanol
b. methyl iodide, NaOH
c. methanol, dicyclohexylcarbodiimide
d. diazomethane
e. methanol, NaOH

434. Secondary Level of Protein Structure. Which of the following statement about protein structure is true?
a. The primary structure of a protein is an amide covalently linked with α-glycosidic linkages.
b. X-ray analysis shows that the 3D arrangement of proteins is composed of repeating units with certain specific distances
between them.
c. Lipophilic parts are turned outward each other and points into the water.
d. Fibrous proteins are more folded than globular proteins.
e. All statements are false.
435. Formation of a Pleated Sheet. Which of the following statements about pleated sheet formation is true?
a. Pleated sheet or β configuration is preferred to give small and medium sized R-groups room enough to avoid van der Waals
repulsions in the non-planar amide linkage.
b. Six atoms of the peptide bonds of the amide linkage are coplanar because of the considerable high double bond character
of the C-N linkage brought by resonance.
c. R groups attached to N and C cannot rotate because of van der Waals attraction.
d. A repeat distance of approximately 7.2 angstrom is observed for pleated sheet structures.
e. All are false.

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436. α-Helix. Which of the following statements about α-helix formation is false?
a. α-helix structures are right handed and have approximately 3.6 amino acid residues per turn.
b. α-helix is predominant in structures of fibrous protein such as myosin found in the bones and α-keratin found in nails.
c. Peptides with proline and derivatives of proline have kinks or bends in their structure because these amino acids contain α-
carbon bonds which cannot rotate to form α-helical structure.
d. Lipophilic parts are turned inward toward each other and away from water, like the lipophilic tails in soap micelles.
e. Biological activity of a protein depends not only upon its prosthetic group and its particular amino acid sequence, but also
depends upon its molecular shape.
437. Intermolecular Forces on 20 Structure. The following intermolecular forces of attraction stabilizes 20 structure except
a. van der Waals
b. H-bonds
c. interionic attraction between charged groups
d. chemical cross-linking by disulfide bonds
e. all are IMFA’s which stabilize 20 structure

438. Tertiary Structure. Which of the following statements about 30 structure of proteins is false?
a. The 3D structure of proteins arises from the further foldings of its polypeptide chains superimposed on coils of the α-
helices.
b. Forces stabilizing the tertiary structure include disulfide bonds, polar (hydrophilic) groups exposed to aqueous environment
and nonpolar (hydrophobic) groups in its interior.
c. Fibrous proteins are more folded than globular proteins.
d. α-keratin is a superhelix wound to a ropelike structure of seven strands.
e. Like enzymes, proteins are highly specific, depending on the overall 30 structure.
439. Synthesis of Heterocyclic Compounds. Which of the following reactions won’t result in a heterocyclic compound?
a. Furan + ammonia, water, AlCl3, 4000C
b. C5H10O5 (pentose) + (1) acidic water, (2) Ni
c. 1,3-butadiene + S, 6000C
d. All will result to a heterocyclic compound.
e. All won’t result to a heterocyclic compound.

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440. Primary Structure of Nucleic Acids. Which of the following statements regarding the primary structure of nucleic acids is false?
a. Adenine and guanine are purine bases while cytosine, thymine and uracil are pyrimidine bases.
b. Mild degradation of nucleic acids produces their monomeric units called nucleotides, a base-sugar-phosphoric acid unit.
c. The nucleic acid is a polyester molecule derived from the polyester chain of phosphoric acid and sugar units (D-ribose for
RNA and D-2-deoxyribose for DNA)
d. Removal of the phosphate group of a nucleotide coverts it to a base-sugar unit called nucleoside.
e. Uridine-5’-phosphate is the nucleoside of uracil, a pyrimidine found only in RNA.
441. Primary Structure of Nucleic Acids. Which of the following statements regarding the primary structure of nucleic acids is false?
a. In nucleotides obtained from DNA, the sugar component is 2’-deoxyribose where the OH at the position 2’ is replaced by
–H.
b. The phosphate group of a nucleotide may be attached to the 5’-carbon or to the 3’-carbon.
c. The heterocyclic base is always attached through a β-glycosidide linkage at C-1’.
d. In RNA, the nucleic acid uracil is replaced by thymine.
e. Numbering at the sugar unit is indicated by an apostrophe.

442. Secondary Structure of Nucleic Acids. Which of the following reactions about the secondary structure of nucleic acids is true?
a. Proposed by Watson and Crick, the secondary structure of a nucleic acid is a double helix, each of the nucleic acids on each
strand held together by covalent bonds.
b. Adenine always pair with guanine and thymine always pair with cytosine in DNA or uracil in RNA.
c. Cytosine-Guanine base pairs are weaker than Adenine-Thymine base pairs.
d. Both helices of the double helix model are right handed.
e. All are false.
443. Degradation of Nucleic Acids with Acids and Bases. Single stranded-CCCCCC + H+ in mild conditions →
a. cytosine-5’-phosphate molecules
b. deoxyadcytidine molecules
c. cytosine molecules + deoxyribose molecules
d. cytosine molecules + deoxyribose molecules + phosphate ions
e. none of the above
444. Nucleosides. The nucleosides

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a. are resistant to acids


b. cannot be attacked by bases at the β-glycosidic linkage
c. are not hydroylzable at the oxygen-phosphate bonds
d. all can fit in
e. none could fit in
445. Mutations. Tautomerizatin causes mutation in the heterocyclic bases because
a. their resistivity to bases and hydrolysis is removed after tautomerization
b. there is a change in the degree of H-bonding
c. there are bond formations and cleavages
d. all of the above
e. none of the above
446. Reactions of the Heterocyclic Bases. Which of the following is true regarding the reactivity of the nucleic bases?
a. Pyrimidine bases can be attacked at the C-6 carbon, because of the polarizability of the C5-C6 double bond.
b. Purine bases are less stable than pyrimidine bases.
c. Electrophilic attack at the eight carbon of purine bases is more favorable than nucleophilic attacks.
d. The basic amino groups of adenine and cytosine can be a site of alkylation and diazotization.
e. All are true.

447. Reactions of Cytosine and Adenine. Cytosine + (1) formaldehyde, (2) formic acid →

a.

b.

c.

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d.
e. none of the above
448. Metabolism. Which of the following statements about metabolism is false?
a. Metabolism is a collective term for the reactions that take place in the cell of living organisms.
b. Catabolism is the pathway by which organisms carry out their chemistry on how for example they metabolize fats,
carbohydrates, and proteins.
c. Anabolism is the pathway that synthesize larger molecules from smaller ones.
d. Catabolism involves Acetyl CoA formation, Citric Acid Cycle and Electron Transport Chain.
e. Catabolic reactions absorb energy while anabolic reactions release energy.

449. Catabolism. Which of the following stages of catabolism is true?


a. Food is broken down in mouth, stomach, small intestine by hydrolysis of ester, glycoside (acetal) and peptide bonds to yield
primarily fatty acids, simple sugars and amino acids.
b. Smaller molecules are further degraded in the cytoplasm of cells to yield acetyl groups attached to the larger carrier molecule
acetyl coenzyme A.
c. Acetyl groups are oxidized inside cellular mitochondria through the citric acid cycle to yield carbon dioxide.
d. The electron transport chain produce molecules of the nucleotide adenosine triphosphate, ATP, the final result of food
catabolism from ADP, adenosine diphosphate, and hydrogen phosphate ion (HPO42-)
e. All are true.
450. Anabolism. Which of the following statements of anabolism is true?
a. It requires the utility of ADP.
b. Glucose is converted to Glucose-σ-phosphate
c. With ATP, the ∆G0 of the reaction of anabolism increases.

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d. All are true.


e. All are false.
451. Coenzymes. Which of the following statements about common coenzymes is false?
a. Catabolism pays off with ATP while anabolism spends ATP.
b. Reduced nicotinamide adenine dinucleotide (NADH) is often involved as a biochemical oxidizing agent for converting
alcohols to ketones or aldehydes.
c. Reduced Flavin adenine dinucleotide (FADH2) is involved in the introduction of conjugated double bonds into carbonyl
compounds.
d. Pyridoxal Phosphate is involved in amino acid metabolism especially in trans-amination reactions.
e. Thiamine Diphosphate (TPP) is involved in the conversion of acetyl to pyruvate.
452. ATP. The conversion of ADP to ATP requires which of the following reagents?
a. OH-, H2O
b. HPO42-, H+
c. H+
d. OH-
e. H2O

453. Acetyl CoA. Involved in the metabolism of food molecules and in numerous other biological pathways, acetyl CoA is a thioester
with which of the following bases
a. guanine-3’,5’-biphosphate
b. adenine-3’,5’-biphosphate
c. cytosine-3’,5’-biphosphate
d. thymine-3’,5’-biphosphate
e. uracil-3’,5’-biphosphate
454. NAD. CH3CH2OH ---- Zn+2 + NAD+ →
a. CH3CH(OH)2
b. CH3C(OH)3
c. CH3CH2O-
d. CH3CHO
e. CH3CH2OCH2CH3
455. Pyridoxal Phosphate. Alanine + -O2CCH2CHC(C=O)CO2- →

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a. Alanyl pyruvate
b. -O2CCH2CHCCHNH2CO2-
c. Glyceraldehyde
d. Both a and b
e. Both b and c
456. Nucleophilic Acyl Substitution Reactions in the Cell. Which of the following reactions in the living cell is not considered as a
nucleophilic substitution?
a. Phosphorylation of glycerol
b. Dephosphorylation of glycerol
c. Alcohol + ATP
d. All are nucleophilic acyl substitution
e. None are nucleophilic acyl substitution
457. ATP. Ethanol + ATP →
a. ADP
b. Ethanol phosphate ester
c. Ethanol pyruvate
d. Both a and b
e. Both a and c
458. Elimination Reactions in Living Cell. The elimination of water molecule from 2-phosphoglycerate with enolase enzyme
happens via
a. SN2
b. SN1
c. E2
d. E1
e. it won’t happen
459. Dehydrogenation. succinate → fumarate
a. ATP
b. NAD+
c. FADH2
d. NADH
e. FAD
460. Introduction of Conjugation. RCH2CH2(C=O)-SCoA + FAD →

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a. RCH2CH2CH2SCoA
b. cis-RCHCHCH2SCoA
c. trans-RCHCHCH2SCoA
d. RCH2CH2CH3
e. RCH2CH2COOH
461. Isomerization. Isomerization of biomolecules is possible with
a. hydratase
b. isomerase
c. synthase
d. tautomerase
e. dehydratase
462. Synthesis in the Living Cell. Synthase is used in which of the following reactions
a. Claisen Condensation
b. Wittig Reaction
c. Aldol Condensation
d. Wolf-Kishner Reduction
e. Both a and c

463. β-oxidation Pathway of Fatty Acids. The first step in the catabolism pathway of fatty acids involves the conversion of the
saturated fatty acid to an unsaturated fatty acid. Which coenzyme could be used?
a. NADH
b. FAD
c. ATP
d. H2O
e. OH-
464. β-oxidation Pathway of Fatty Acids. CH3CH2(C=O)-SCoA + NADH →
a. CH3CH2CH2-SCoA
b. CH2CH(C=O)-SCoA
c. CHC(C=O)-SCoA
d. CH3CH2COH-SCoA
e. CH3CH2COOH
465. β-oxidation Pathway of Fatty Acids. Answer in (464) + H2O →

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a. CH3CH2CH2OH
b. CH2OHCH(C=O)-SCoA
c. CH(OH)2C(OH)(C=O)-SCoA
d. CH3CH2COH-SCoA
e. CH3CH2COOH
466. β-oxidation Pathway of Fatty Acids. Answer in (465) + NAD+ →
a. CH3CH2CHO
b. H(C=O)H(C=O)-SCoA
c. H(C=O)(C=O)(C=O)-SCoA
d. CH3CH2(C=O)-SCoA
e. CH3CH2COOH
467. β-oxidation Pathway of Fatty Acids. Answer in (466) → (Retro-Claisen Condensation products)
a. Ethyl CoA
b. Acetyl CoA
c. Propyl CoA
d. Ethanoic Acid
e. Propanoic Acid

468. Odor. Odor can be used to detect low molecular weight compounds because
a. They can easily react with water vapor producing odorized compounds
b. They are highly volatile
c. They have high boiling points and melting points
d. They can crystalize odorized particles
e. Their electron crashes to each other and produce odor
469. Ignition Test for Organic Compounds. A sooty yellow flame indicates that the compound is
a. Saturated aliphatic hydrocarbon
b. Unsaturated aliphatic hydrocarbon
c. Aromatic aliphatic hydrocarbon
d. O-containing compound
e. An organometallic compound
470. Spectroscopy. Which of the following statements about spectroscopy is false?
a. UV-Vis spectrometer measures electron excitation

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b. IR spectrometer measures molecular vibration


c. NMR measures electron spin
d. Mass Spectrometer detects ion mass fragment
e. All can be used to determine structural information about organic compounds
471. Electronic Excitations. The following electronic excitations can be found on formaldehyde except
a. Sigma-sigma star
b. Pi-pi star
c. Non bonding to pi star
d. Non bonding to sigma star
e. All can be found in formaldehyde
472. Signals. The highest peak in the UV Vis spectrum of formaldehyde corresponds to which electronic transition?
a. Sigma-sigma star
b. Pi-pi star
c. Non-bonding to pi star
d. Non-bonding to sigma star
e. Pi-sigma star

473. Lambda max. Which of the following statement is false?


a. The more the number of conjugated pi bonds, the larger is the lambda max.
b. Cyclic polyenes absorb at higher wavelengths than acyclic ones.
c. Substitution of alkyl groups on C=C causes a shift to longer wavelength.
d. As the electron are farther away from the attraction of the nucleus, the more difficult to excite them at higher wavelengths.
e. Steric strain which prevents coplanarity lowers the lambda max.
474. Color and Unsaturation. Which of the following polyene has the least conjugation?
a. Polyene which absorbs violet light
b. Polyene which absorbs orange light
c. Polyene which emits red light
d. Polyene which absorbs green light
e. Polyene which emits blue light
475. Infrared Spectroscopy. Which of the following statements regarding IR Spectroscopy is true?
a. The infrared spectrometer measures the absorption of energy due to electronic vibrations.

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b. Only vibrations that has a net dipole moment of zero can produce absorption bands.
c. No IR band can be observed for CO2.
d. IR absorption can be produced from unsymmetrical stretches.
e. Each bond and group absorbs at a specific wavelength and can produce any of the vibrational states.
476. Stretching bands. Which of the following statements is false?
a. CH, OH and NH bonds are found approximately in wavenumbers above 3000.
b. Saturation on C-C bonds decreases wavenumber signals but hybridization on C-H bonds increases with increasing s
character.
c. Carbonyl absorbs strongly at ~1500 cm-1.
d. Water broadens the OH peak and shifts common stretching frequencies to lower ones.
e. Aromaticity can be identified by checking overtones at ~1650 cm-1.
477. Nuclear Magnetic Resonance. The following are NMR active nuclei except
a. 1H
b. 2H
c. 14N
d. 32S
e. 31P

478. 1H-NMR. Which of the following statement is true?


a. Hydrogen has two equal-energy nuclear spin states with quantum number +1 and -1.
b. An applied electric field split the spin-states into two, the aligned and unaligned spin states.
c. The required frequency needed to flip the electrons of 1H is inversely proportional to the magnetic field.
d. The NMR spectrum is a plot of electric field versus transmittance.
e. All are false.
1
479. H-NMR Chemical Shifts. Which of the following statement about 1H-NMR chemical shifts is false?
a. The electrons in a bond next to the H atom and nearby pi bonds induce their magnetic field, which can either oppose or
reinforce the field sensed by the H atom.
b. When the induced field reinforces the applied field, the atom is deshielded and absorbs downfield
c. When the induced field opposes the applied field, the atom is shielded and absorbs at higher wavelengths.
d. The peak of tetramethyl silane, (CH3)4Si, is used as the reference point in the NMR Spectrum.
e. The smaller sigma and larger tau, the more downfield is the peak.
480. Molecular Structure and Chemical Shifts. Which of the following statement is false?

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a. Electronegative atoms such as N, O and X deshields H's.


b. EWG deshields H's.
c. EDG deshiels H's.
d. Electropositive atoms such as Silicon shields H's.
e. H's attached to a cyclopropane ring is strongly shielded.

481. Structure Elucidation. Give the structure of C9H12 with shifts as follows δ (7.1, 2.2, 1.5, and 0.9 ppm)

a.

b.

c.

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d.
e. None of the sbove
482. Non-equivalent H's. Which of the following has the largest number of non-equivalent hydrogens?

a.

b.

c.
d. CH3CHClCH2CH3
e. N-Succinic Bromide

483. Spin-spin coupling. Given the compound below, which of the following statement is false?
a. In half of the molecule, Ha are spin up and Hb are spin down.
b. Hb appears as a quartet.
c. Ha split into 3 spins with the intensity ratio of 1:2:1.
d. The entire triplet is integrated as 1 H atom.
e. Splitting is observed because of nonequivalent H atoms.
484. Splitting. Splitting is observed in the following molecules except
a. ClCH2CH2I
b. Z-1,2-dichloroethene
c. E-1,2-dichloroethene
d. 1,1-dichloroethene
e. all produces splitting pattern

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485. Mass Spectroscopy. Which of the following statements about mass spectroscopy is false?
a. In mass spectroscopy, the molecule is exposed to bombardment of a beam of high energy electrons and consequently
ionized in the vapor state.
b. Sharp peaks appear at the values of m for various cations.
c. The highest peak is the most stable fragment of the molecule.
d. The fragmentation may result to neutral species.
e. The largest observed x-axis value belongs to the parent molecule.
486. Determination of Molecular Ion via Mass Spectroscopy. Which of the following statements is false?
a. Molecular ions or parent molecule of hydrocarbons containing C-H have always even m/e values.
b. For compounds containing C, H, N and O, the molecular ion will have an odd m/e if N is odd.
c. Electrons in the highest energy MO is most likely to be lost.
d. Branched chain alkanes has higher intensity molecular ion peak than straight chain alkane.
e. Molecular ions of compounds containing C, H and O have even m/e values.
487. Fragmentation. Which of the following fragmentation patterns of formaldehyde is the easiest to happen?
a. H2C=O → HC+=O + •H
b. H2C=O → H2C+-O + π e-
c. H2C=O → H2C2+ + O2-
d. H2C=O → H2C+-O + σ e-
e. H2C=O → H2C=O+ + nonbonding e-

488. m/e Values. Which of the following statement regarding fragmentation values is true?
a. Ethanol has a prominent peak at m/e = 31.
b. Ethyl benzene has a prominent peak at m/e = 91.
c. Ethene has a prominent fragment at m/e = 41.
d. 2-chloroethane has prominent fragments at m/e = 63 and 65.
e. Aldehydes show an intense peak at m/e = 29.
489. Determining Structure of Mass Spectroscopy. What is the structure of C10H12O, whose m/e values are 15, 43, 57, 91, 105 and
148 (M+)?

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a.

b.

c.

d.

e.

490. 1H-NMR as easy as 1,2,3. A compound C5H11Br gives the following NMR spectrum. What is its structure?
δ value Proton Integration Splitting
0.80 6 Doublet
1.02 3 Doublet
2.05 1 Multiplet
3.53 1 Multiplet

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a.

b.

c.

d.

e.

491. 1H-NMR. Deduce the structure of C3H6Cl2 from its NMR spectrum.
δ value Proton Integration Splitting
2.20 2 Quintet
3.80 4 Triplet

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a.

b.

c.

d.

e.

492. Spectroscopic Methods. Identify the compound A from the following data:
Empirical Formula: C3H6O
δ value Proton Integration Splitting
1.7 3 Singlet
4.8 1 Singlet
5.0 1 Singlet

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15.2 1 Singlet
IR Spectrum: signals at 1710 cm and 3400 cm-1 (partial)
-1

a.

b.

c.

d.
e. None of the above

493. Spectroscopic Methods. Deduce the structure of compound A, C9H10O, given that
IR Absorption: ca. 1715 cm-1; no absorption above 3100 cm-1
NMR: 5H singlet at 7.2 δ, 2H singlet at 3.5 δ, 3H singlet at 1.9 δ

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a.

b.

c.

d.

e.

494. Spectroscopic Methods. Deduce the structure of compound A, C6H14O, given that
NMR: 1H singlet at 4.40 δ, 1H quartet at 3.40 δ, 3H doublet at 1.10 δ, 9H singlet at 0.90 δ
Conversion: A is converted to C6H12 by an acid and is converted to C3H6O with a single peak at 2.1 δ upon reductive ozonolysis.
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a.

b.

c.

d.

e.
495. Challenged? Deduce the structure of Compound A from the following information
IR spectrum: contains a strong peak at 3400 cm-1
Mass spectrum: contains peaks at m/e: 136, 118, 107, 79, 77, 51 and 38
1
H-NMR spectrum: 0.8 δ, triplet, 3H; 1.6 δ, quartet of broad peaks, 2H; 3.9 δ, broad singlet, 1H; 4.3 δ, triplet, 1H; 7.2 δ, singlet, 5H

-END OF ORGANIC CHEMISTRY SECTION-

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