Organic Mock Exam Questions
Organic Mock Exam Questions
Organic Mock Exam Questions
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!
1
OrgChem | Santiago | 2015
2
OrgChem | Santiago | 2015
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
3
OrgChem | Santiago | 2015
4
OrgChem | Santiago | 2015
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
5
OrgChem | Santiago | 2015
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
6
OrgChem | Santiago | 2015
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
7
OrgChem | Santiago | 2015
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
8
OrgChem | Santiago | 2015
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.
9
OrgChem | Santiago | 2015
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
10
OrgChem | Santiago | 2015
11
OrgChem | Santiago | 2015
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?
12
OrgChem | Santiago | 2015
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)
13
OrgChem | Santiago | 2015
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.
14
OrgChem | Santiago | 2015
65. Electrophilic Aromatic Substitution. The rate determining step of the bromination of benzene is the formation of
a. b. c. d. e.
15
OrgChem | Santiago | 2015
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
16
OrgChem | Santiago | 2015
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)
17
OrgChem | Santiago | 2015
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
18
OrgChem | Santiago | 2015
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
19
OrgChem | Santiago | 2015
81. Nucleophilic Aromatic Substitution. Which substituted aryl halide will react with KH2/NH3 fastest?
a.
b.
c.
d.
e.
20
OrgChem | Santiago | 2015
83. Reactivity of Fused Aromatic Rings. + 1.) KMnO4, OH-, heat and 2.) H+ →
a. b. c. d. a and c e. a and b
a. b. c. d. e.
a. b. c. d. e. No Reaction
21
OrgChem | Santiago | 2015
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
a. d.
22
OrgChem | Santiago | 2015
b. e.
c.
a. d.
b. e.
23
OrgChem | Santiago | 2015
c.
24
OrgChem | Santiago | 2015
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?
25
OrgChem | Santiago | 2015
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
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
26
OrgChem | Santiago | 2015
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
27
OrgChem | Santiago | 2015
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
28
OrgChem | Santiago | 2015
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
29
OrgChem | Santiago | 2015
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
30
OrgChem | Santiago | 2015
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
31
OrgChem | Santiago | 2015
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
32
OrgChem | Santiago | 2015
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
33
OrgChem | Santiago | 2015
a. b. c. d. e. Mixture of a and b
34
OrgChem | Santiago | 2015
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
35
OrgChem | Santiago | 2015
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.
36
OrgChem | Santiago | 2015
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
37
OrgChem | Santiago | 2015
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?
38
OrgChem | Santiago | 2015
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
39
OrgChem | Santiago | 2015
40
OrgChem | Santiago | 2015
41
OrgChem | Santiago | 2015
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
42
OrgChem | Santiago | 2015
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
43
OrgChem | Santiago | 2015
44
OrgChem | Santiago | 2015
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
45
OrgChem | Santiago | 2015
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
46
OrgChem | Santiago | 2015
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, ∆
47
OrgChem | Santiago | 2015
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
48
OrgChem | Santiago | 2015
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
49
OrgChem | Santiago | 2015
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.
50
OrgChem | Santiago | 2015
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
51
OrgChem | Santiago | 2015
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
52
OrgChem | Santiago | 2015
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
53
OrgChem | Santiago | 2015
54
OrgChem | Santiago | 2015
55
OrgChem | Santiago | 2015
56
OrgChem | Santiago | 2015
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?
57
OrgChem | Santiago | 2015
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
58
OrgChem | Santiago | 2015
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
59
OrgChem | Santiago | 2015
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
60
OrgChem | Santiago | 2015
c. bromine
d. propane
e. methane
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
62
OrgChem | Santiago | 2015
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
63
OrgChem | Santiago | 2015
64
OrgChem | Santiago | 2015
65
OrgChem | Santiago | 2015
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
66
OrgChem | Santiago | 2015
67
OrgChem | Santiago | 2015
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
68
OrgChem | Santiago | 2015
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
69
OrgChem | Santiago | 2015
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
70
OrgChem | Santiago | 2015
71
OrgChem | Santiago | 2015
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
72
OrgChem | Santiago | 2015
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
73
OrgChem | Santiago | 2015
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
74
OrgChem | Santiago | 2015
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.
75
OrgChem | Santiago | 2015
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
76
OrgChem | Santiago | 2015
a.
b.
c.
d.
e.
77
OrgChem | Santiago | 2015
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
78
OrgChem | Santiago | 2015
79
OrgChem | Santiago | 2015
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
80
OrgChem | Santiago | 2015
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
81
OrgChem | Santiago | 2015
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
82
OrgChem | Santiago | 2015
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
83
OrgChem | Santiago | 2015
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
84
OrgChem | Santiago | 2015
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.
85
OrgChem | Santiago | 2015
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.
86
OrgChem | Santiago | 2015
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 →
87
OrgChem | Santiago | 2015
a. 2-aminopyridine
b. 3-aminopyridine
c. 4-aminopyridine
d. mixture of a and c
e. none of the above
88
OrgChem | Santiago | 2015
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.
89
OrgChem | Santiago | 2015
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
90
OrgChem | Santiago | 2015
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
91
OrgChem | Santiago | 2015
398. What Reaction. N,N-dimethylcyclohexamine + (1) methyl iodide (2) Ag2O, heat →
a.
b.
c.
d.
e.
92
OrgChem | Santiago | 2015
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.
93
OrgChem | Santiago | 2015
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.
94
OrgChem | Santiago | 2015
95
OrgChem | Santiago | 2015
96
OrgChem | Santiago | 2015
97
OrgChem | Santiago | 2015
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.
98
OrgChem | Santiago | 2015
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
99
OrgChem | Santiago | 2015
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.
100
OrgChem | Santiago | 2015
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.
101
OrgChem | Santiago | 2015
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
102
OrgChem | Santiago | 2015
447. Reactions of Cytosine and Adenine. Cytosine + (1) formaldehyde, (2) formic acid →
a.
b.
c.
103
OrgChem | Santiago | 2015
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.
104
OrgChem | Santiago | 2015
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- →
105
OrgChem | Santiago | 2015
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 →
106
OrgChem | Santiago | 2015
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 →
107
OrgChem | Santiago | 2015
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
108
OrgChem | Santiago | 2015
109
OrgChem | Santiago | 2015
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
110
OrgChem | Santiago | 2015
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.
111
OrgChem | Santiago | 2015
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
112
OrgChem | Santiago | 2015
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+)?
113
OrgChem | Santiago | 2015
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
114
OrgChem | Santiago | 2015
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
115
OrgChem | Santiago | 2015
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
116
OrgChem | Santiago | 2015
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
117
OrgChem | Santiago | 2015
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.
118
OrgChem | Santiago | 2015
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
119