ADVANCED ORGANIC CHEMISTRY

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1. When two groups are lost, both groups are lost from the same atom to give a carbene (or a
nitrene) the reaction is called:
a. α-elimination b. β-elimination c. ɤ-elimination
2. When two groups are lost from adjacent atoms so that a new double (or triple) bond is formed the
reaction is called:
a. α-elimination b. β-elimination c. ɤ-elimination
3. When two groups are lost that three-membered ring is formed the reaction is called:
a. α-elimination b. β-elimination c. ɤ-elimination
4. If the two groups depart simultaneously, with the proton being pulled off by a base the
machanism is:
a. E1 b. E2 c. E1cb
5. If proton loses by a strong base and then followed by departed leaving group the mechanism is:
a. E1 b. E2 c. E1cb

6. If leaving group depart first followed by loses proton to a base the machanism is:
a. E1 b. E2 c. E1cb

7. In molecule R-CH2-CHX-R, if H and X depart in one direction to form R-CH=CH-R, the

elomination is called:
a. anti-elimination b. syn-elomination c. cyclic-elimination
8. In molecule R-CH2-CHX-R, if H and X depart in opposite direction to form R-CH=CH-R. The
reaction is called:
a. Anti-elimination b. syn-elimination c. cyclic-elimination
9. Which one these molecules below if eliminated to form cis alkene?

a. b. c.
10. The intermediate for E1cb mechanism is:

a. b. c. neither

A B C D
11. If A undergo elimination reaction the product is:
a. C b. D c. Both
12. If B undergo elimination reaction the product is:
a. C b. D c. neither
13. Elimination from 2-bromo-pentane will give dominant product :
a. 1-pentene b. cis-2-pentene c. trans-2-pentene
14. Zaitsef elimination from 2 bromo butane formed:
a. cis-2-butena dominant b. trans-2-butene dominant c. both equally
15. Elimination is favored over substitution by increasing temperature, whether the mechanism is first
or second order. The reason is:
a. Ea SN > Ea E b. Ea E > Ea SN c. both
16. A positive species approaches the double or triple bond and in the first step forms a bond by
donation of the p pair of electrons to the electrophilic species to form a σ pair, the mechanism is
called:
a. Nucleophilic addition b. Electrophilic addition c. cyclic addition
17. A negative species brings its pair of electrons to one carbon atom of the double or triple bond,
creating a carbanion. The second step is combination of this carbanion with a positive species,
the mechnism is called:
a. Nucleophilic addition b. Electrophilic addition c. cyclic addition
18. The initial attack is not at one carbon of the double bond, but both carbons are attacked
simultaneously.The mechanism is called:
a. Nucleophilic addition b. Electrophilic addition c. cyclic addition
19. Which subtrate will react fastes if it react under electrophilic addition?
a. CCl3CH=CH2 b. CH3CH2=CH2 c. ClCH2CH=CH2
20. Which subtrate will react fastes if it react under nucleophilic addition?
a. CCl3CH=CH2 b. CH3CH2=CH2 c. ClCH2CH=CH2
21. The positive portion of the reagent goes to the side of the double or triple bond that has more
hydrogens, this is:
a. Zaitsev’s rule b. Hoffman’s rule c. Markovnikov’ s rule

H3C H
1 CH3
H3C
2
3
HCl
H H
22. On the reaction above, hydrogen goes to carbon atom numbered?
a. 1 b. 2 c. 3
23. On the reaction above, cloride goes to carbon atom numbered?
a. 1 b. 2 c. 3
24. YW is added to the cis isomers of an alkene of the form ABC=CBA, the product is threo dl pair,
the addition is:
a. Syn b. Anti c. Simultan
25. YW is added to the cis isomers of an alkene of the form ABC=CBA, the product is erythro dl pair,
the addition is:
a. Syn b. Anti c. Simultan

26. YWis added to the trans isomers of an alkene of the form ABC=CBA, the product is threo dl pair,
the addition is:
b. Syn b. Anti c. Simultan

27. YWis added to the trans isomers of an alkene of the form ABC=CBA, the product is erithro dl pair,
the addition is:
a. Syn b. Anti c. Simultan

28. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither

29. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither

30. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither

31. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither

32. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither

33. The regiochemistry of is:

a. Markovnikov b. Anti-Markovnikov c. Neither
34. In a rearrangement reaction, migrating group move with its electron pair, these can be called ...
arrangements.
a. Cationotropic b. Anionotropic c. Free-radical
35. In a rearrangement reaction, migrating group move without its electron pair, these can be called
... arrangements.
a. Cationotropic b. Anionotropic c. Free-radical
36. In a rearrangement reaction, migrating group move with just one electron, these can be called ...
arrangements.
a. Cationotropic b. Anionotropic c. Free-radical

37. Nucleophilic rearrangement have three steps, the actual migration is in....
a. First step b. Second step c. Third step
38. First step in free-radical rearrangements is formation of:
a. Radical b. Abstraction radical c. Molecule
39. Electrophilic rearrangements have three steps, formation of anion is in...
a. First step b. Second step c. Third step

A B C
40. Rearrangements reaction with 1,2-shift is.... (reaction above)
a. A b. B c. C
41. Rearrangements reaction with 1,3-shift is.... (reaction above)
a. A b. B c. C
42. Rearrangements reaction with 1,4-shift is.... (reaction above)
a. A b. B c. C
43. Free-radical reaction mechanism rate depend on....
a. Initiation step b. termination step c. both step
44. In propagation step free-radical mechanism bond cleavages occur is...
a. Homolytic b. Heterolytic c. Both
45. Radicals can abstract hydrogen or other atoms from many types of solvents and reagents. This is
occur in....
a. Initation step b. Propagation steps c. Termination steps.
46. Source of radical intermediates is.....
a. Benzoyloxide b. Azo compounds c. Esterperoxide
47. The geometry of methyl radical is.....
a. Planar b. Symmetric c. Pyramid
48. Radical can be stabilized by substituents. Kind of substituents is....
a. Donating electrons b. Withdrawing electrons c. Both of them
49. Radical can found in many form. Exception is ....
a. Molecule radicals b. Anion radicals c. Cation radicals
50. Free radical chain oxidations that can cause deterioration of many commercial materials derived
from organic molecules, including foodstuffs, petroleum products, and plastics. Which one is use
to stop the reaction?
a. TEL b. PCC c. BHA
51. Abstraction hydrogen with methyl radical is most easy occur in....
a. CH3-H b. CH3CH2-H c. (CH3)2CH-H
52. F· + CH3CH3 → CH3F + ·CH3 is occur in ..... of free-radical mechanism.
a. Initiation step b. Propagation steps c. Termination steps
53. Products of reaction under free-radical mechanism will formed in....
a. Termination steps b. Propagation steps c. Both steps
54. A Perucyclic reaction is one that occurs by a concerted process through a.....
a. Cationic intermediate b. Anionic intermediate c. Transition state
55. Pericyclic reactions pathway is determined by ...... properties that are directly involved
a. Orbitals symmetry b. Orbital size c. Orbitals hybridized
56. Ethene, CH2=CH2, the lobes of MO’s have algebraic sign......
a. HOMO: + + b. LUMO: + + c. HOMO: + -
57. In the ground state condition the lobes of MO’s of 1,3-butadiene have algebraic sign......
a. HOMO: + + b. LUMO: + - c. HOMO: + -
58. In the ground state condition the lobes of MO’s of 1,3,5-hexatriene have algebraic sign......
a. HOMO: + - b. LUMO: + - c. LUMO: + +
59. In the excited state condition the lobes of MO’s of 1,3-butadiene have algebraic sign......
a. HOMO: + - b. LUMO: + + c. HOMO: + +
60. In the excited state condition the lobes of MO’s of 1,3,5-hexatriene have algebraic sign......
a. HOMO: + + b. HOMO: + - c. LUMO: + -
61. The path of cyclization for conjugated butadiene to cyclobutene by thermal reaction is:
a. Conrotatory b. Disrotatory
62. The path of cyclization for conjugated butadiene to cyclobutene by photochemical reaction is:
a. Conrotatory b. Disrotatory
63. The path of cyclization for conjugated hexatriene to cyclohexadiene by thermal reaction is:
a. Conrotatory b. Disrotatory
64. The path of cyclization for conjugated hexatriene to cyclohexadiene by photochemical reaction is:
a. Conrotatory b. Disrotatory

=A =B =C =D
65. The pair of substrate-product for thermal reaction ring opening is .....
a. A-C b. B-C c. A-D
66. The pair of substrate-product for photochemical reaction ring opening is .....
a. A-C b. B-D c. A-D

=E =F =G =H
67. The pair of substrate-product for thermal reaction ring closure is .....
a. E-H b. F-G c. F-H
68. The pair of substrate-product for photochemical reaction ring closure is
a. E-H b. E-G c. F-H
69. The geometry of triene for compound E is:
a. E, E, E b. E, Z, E c. E, Z, Z
70. The geometry of triene for compound F is:
a. Z, Z, E b. Z, E, Z c. Z, E, E
71. What is reaction condition for forming cyclobutane from two molecules ethene?
a. Thermal reaction b. photochemical reaction
72. What is path of formation cyclobutane from two molecules ethene?
a. Antarafacial b. Suprafacial

1 2 3

4 5 6
73. For reaction number 1, condition and pathway occurs are:
a. Suprafacial-thermal b. Suprafacial-photolysis c. Antarafacial-termal
74. For reaction number 2, condition and pathway occurs are:
a. Suprafacial-thermal b. Antarafacial-thermal c. Suprafacial-photolysis
75. For reaction number 3, condition and pathway occurs are:
a. Suprafacial-thermal b. Antarafacial-thermal c. Antarafacial-photolysis
76. For reaction number 4, condition and pathway occurs are:
a. Suprafacial-thermal b. Antarafacial-thermal c. Antarafacial-photolysis
77. For reaction number 5, condition and pathway occurs are:
a. Suprafacial-photolysis b. Antarafacial-thermal c. Antarafacial-photolysis
78. For reaction number 6, condition and pathway occurs are:
a. Suprafacial-thermal b. Antarafacial-thermal c. Antarafacial-photolysis
CH3 CH3
H3C H CH3 H3C H CH3 CH3
A
CH3 X
CH2 A
H3C CH3 H3C CH3 O CH3 O CH3
CH3 CH3
H2C X
CH3
I CH3
J CH2 K
79. A [3,3]-Sigmatropic Rearrangement reaction is......
a. I b. J c. K
80. A [3,3]-Sigmatropic Rearrangement reaction is......
a. I b. J c. K
81. A [3,3]-Sigmatropic Rearrangement reaction is......
a. I b. J c. K

L M N
82. To obtain the product L, the reaction involved are....
a. Elctrocyclic b. Cycloadittion c. Both
83. To obtain the product M, the reaction involved are....
a. Electrocyclic b. Cycloaddition c. Sigmatropic rearrangements

84. To obtain the product N, the reaction involved are....

a. Electrocyclic b. Cycloaddotion c. Sigmatropic rearrangements

0 and P Q R S T
85. The relationship between two compound is.....
a. Enantiomer b. Diastreomer c. mesomer
86. Absolute configuration at chiral carbon (compound Q)are:
a. R b. S c. R, S
87. The geometry of molecules R and S in order are:
a. Z - Z b. E - E c. Z – E
88. How many streoisomer of compound T?
a. 2 b. 4 c. 6
89. Hydeogenation of 2-butanon will generated (R) 2-butanol and (S) 2-butanol. Which one dominant
product?
a. R form b. S form c. no one dominant
90. The Fisher projection of same enantiomer will differ by rotation....
a. 90o b. 180o c. 270o
91. The Fisher projection of differ enantioner will differ by rotation....
a. 180o b. 270o c. 360o
92. Enantiomers have identical physical properties except for
a. Melting point b. spesific gravity c. rotation of plane polarized light
93. If a reaction occurs at a chiral atom, what will be at it configuration?
a. Inversion b. Retention c. Both
For number 94 to 101 choose the most stable member of each threesome.

94. 98.

95. 99.

96. 100.

97. 101.
102. If a reaction shows a preference for one of the stereoisomers, it iscalled:
a. Stereoselective b. Stereospesific c. Regioselective
103. If a reaction in which stereoisomeric reactants each provide stereoisomeric products, it called:
a. Stereoselective b. Stereospesific c. Regiospesific

A B C D E F
104. Conformation butane above which are gauche form?
a. A and B b. B and D c. C and E
105. Conformation butane above wich are eclips form?
a. A and E b. B and D c. C and E
106. Conformation butane above wich are anti form?
a. A b. C c. E