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MULTIPLE CHOICE
a. primary
b. secondary
c. tertiary
d. quaternary
ANS: B
a. primary
b. secondary
c. tertiary
d. quaternary
ANS: C
3. Which of the following concepts explains why tertiary carbocations are more stable than primary and
secondary carbocations?
a. electronegativity
b. resonance
c. hyperconjugation
d. the octet rule
ANS: C
4. What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation?
a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital
b. 3° C 2p atomic orbital + methyl C−H σ molecular orbital
c. 3° C sp2 atomic orbital + methyl C−H σ molecular orbital
d. 3° C 2p atomic orbital + methyl C 2s atomic orbital
ANS: B
5. Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to
propene?
a. the relative stability of carbocations
b. the nucleophilicity of bromide anion
c. the acidity of HBr
d. the Aufbau principle
6. What is the correct order of stability of the following carbocations (more stable > less stable)?
a. 1>2>3
b. 1>3>2
c. 3>1>2
d. 3>2>1
ANS: D
7. What is the correct order of stability of the following carbocations (more stable > less stable)?
a. 1>2>3
b. 2>1>3
c. 2>3>1
d. 3>2>1
ANS: C
8. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
a. 1
b. 2
c. 3
d. 4
ANS: B
10. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: C
11. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: C
a. 1
b. 2
c. 3
d. 4
ANS: B
13. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration
(treatment with aqueous H2SO4)?
a. 1
b. 2
c. 3
d. 4
ANS: B
14. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: C
a. 1
b. 2
c. 3
d. 4
ANS: C
16. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
17. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
a. 1
b. 2
c. 3
d. 4
ANS: B
19. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: C
20. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
a. 1
b. 2
c. 3
d. 4
ANS: B
22. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: C
23. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
a. 1
b. 2
c. 3
d. 4
ANS: C
25. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: D
26. What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene?
a. (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
b. (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
c. (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
d. (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane
ANS: C
27. What is (are) the major organic product(s) obtained from the following reaction?
1. (2R,3R)-dibromobutane
2. (2S,3S)-dibromobutane
3. meso-2,3-dibromobutane
a. only 1
b. only 2
c. only 3
d. only 1 and 2
28. What is (are) the major organic product(s) obtained from the following reaction?
1. (2R,3R)-dibromobutane
2. (2S,3S)-dibromobutane
3. meso-2,3-dibromobutane
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D
29. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: B
30. What is the major organic product obtained from the following reaction?
31. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
ANS: D
32. What is (are) the major organic product(s) obtained from the following reaction?
1. (2R,3R)-butanediol
2. (2S,3S)-butanediol
3. meso-2,3-butanediol
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D
1. (2R,3R)-butanediol
2. (2S,3S)-butanediol
3. meso-2,3-butanediol
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: C
34. What is (are) the major organic product(s) obtained from the following reaction?
a. only 1
b. only 2
c. only 3
d. only 2 and 3
ANS: A
35. What is the best choice of reagent(s) to perform the following transformation?
a. H2O, H2SO4
b. HgSO4; followed by NaBH4
c. BH3; followed by H2O2
d. OsO4; followed by NaHSO3
ANS: D
a. Br2
b. HBr
c. Br2, H2O
d. N-bromosuccinimide
ANS: C
37. What is the best choice of reagent(s) to perform the following transformation?
a. H2O, H2SO4
b. Hg(OAc)2 and H2O ; followed by NaBH4
c. B2H6; followed by H2O2, NaOH
d. OsO4; followed by NaHSO3
ANS: C
38. What is the best choice of reagent(s) to perform the following transformation?
a. H2O, H2SO4
b. Hg(OAc)2 and H2O; followed by NaBH4
c. BH3; followed by H2O2, NaOH
d. OsO4; followed by NaHSO3
ANS: B
40. What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a
bromoalkane?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
ANS: A
41. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a
bromohydrin?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
ANS: D
42. What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an
alcohol?
a. carbocation
b. carbanion
c. radical
d. carbene
ANS: A
43. What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an
alcohol?
a. nucleophilic addition
b. electrophilic addition
c. radical addition
d. elimination
ANS: B
45. Which of the following alkenes undergoes the most exothermic hydrogenation upon treatment with
H2/Pd?
a. 1
b. 2
c. 3
d. 4
ANS: D
46. Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with
H2/Pd?
a. 1
b. 2
c. 3
d. 4
ANS: C
47. What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment
with H2/Pd (more exothermic > less exothermic)?
a. 1>2>3
b. 1>3>2
c. 3>2>1
d. 2>3>1
ANS: A
1. (R)-2-bromo-3-methylbutane
2. (S)-2-bromo-3-methylbutane
3. 2-bromo-2-methylbutane
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: C
49. What is (are) the major organic product(s) obtained from the following reaction?
1. (R)-3-methyl-2-butanol
2. (S)-3-methyl-2-butanol
3. 2-methyl-2-butanol
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D
53. Which of the following reactions of alkenes takes place with syn stereospecificity?
a. addition of bromine (treatment with Br2)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)
ANS: B
PROBLEM
1. What is the major organic product obtained from the following reaction?
ANS:
2. What is the major organic product obtained from the following reaction?
ANS:
3. What is the major organic product obtained from the following reaction?
ANS:
ANS:
5. What is the major organic product obtained from the following reaction?
ANS:
6. What is the major organic product obtained from the following reaction?
ANS:
ANS:
8. What is the major organic product obtained from the following reaction?
ANS:
9. What is the major organic product obtained from the following reaction?
ANS:
2 equivalents of
10. What is the major organic product obtained from the following reaction?
ANS:
ANS:
12. What is the best choice of reagent(s) to perform the following transformation?
ANS:
(i) BH3; (ii) H2O2, NaOH
13. What is the best choice of reagent(s) to perform the following transformation?
ANS:
H2O, H2SO4
or
(i) Hg(OAc)2, H2O; (ii) NaBH4
14. What is the best choice of reagent(s) to perform the following transformation?
ANS:
(i) OsO4; (ii) NaHSO3, H2O
15. What is the best choice of reagent(s) to perform the following transformation?
ANS:
H2, transition metal catalyst (e.g., Pt, Pd)
ANS:
Br2
17. What is the best choice of reagent(s) to perform the following transformation?
ANS:
Br2, H2O
18. What is the best choice of reagent(s) to perform the following transformation?
ANS:
HBr
19. What is the best choice of reagent(s) to perform the following transformation?
ANS:
(i) O3 (ii) (CH3)2S
20. Provide the structure of the key intermediate in the following reaction?
ANS:
ANS:
22. Provide the structure of the key intermediate in the following reaction?
ANS:
23. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.
ANS:
The reaction proceeds in two steps:
1. Protonation of propene to form the 2-propyl cation
2. Nucleophilic addition of bromide anion to the 2-propyl cation
ANS:
The reaction proceeds in three steps:
1. Protonation of propene to form the 2-propyl cation
2. Nucleophilic addition of bromine to the 2-propyl cation
3. Deprotonation of the oxygen
25. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.
26. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.
ANS:
The reaction proceeds in three steps:
1. Addition of bromine to propene to afford a cyclic bromonium ion
2. Nucleophilic ring-opening addition of water
3. Deprotonation of oxygen