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A) (Z)-2,3,6-trimethyl-2-heptene
B) (Z)-2,3,6-trimethyl-3-heptene
C) (E)-2,3,6-trimethyl-3-heptene
D) (E)-2,3,6-trimethyl-2-heptene
E) (E)-2,4,6-trimethyl-3-heptene
A) (E)-4-ethyl-3-octene
B) (Z)-4-ethyl-3-nonene
C) (E)-3-ethyl-4-nonene
D) (E)-4-ethyl-3-nonene
E) (E)-5-ethyl-6-nonene
A) (Z)-1-bromo-2-chloro-2-ethyl-4-methyl-1-pentene
B) (E)-1-bromo-1-chloro-2-ethyl-4-methyl-2-pentene
C) (E)-1-bromo-1-chloro-2-ethyl-4-methyl-1-pentene
D) (E)-1-bromo-1-chloro-3-ethyl-4-methyl-1-pentene
E) (Z)-1-bromo-1-chloro-2-ethyl-4-methyl-1-pentene
A) A is a trans alkene.
B) A is an E alkene.
C) A is a cis alkene.
D) Both (A is a trans alkene) and (A is an E alkene) are true.
E) Both (A is an E alkene) and (A is a cis alkene) are true.
A) a: Z; b: Z; c: E; d: E
B) a: Z; b: Z; c: Z; d: E
C) a: E; b: Z; c: E; d: E
D) a: Z; b: E; c: E; d: E
E) a: Z; b: Z; c: E; d: Z
A) A B) B C) C D) D E) E
8. Which of the following compounds has the highest boiling point?
A) A B) B C) C
A) a, b, c D) b, a, c
B) b, c, a E) c, b, a
C) c, a, b
A) a, b, c C) c, a, b
B) b, c, a D) b, a, c
A) A B) B C) C
12. Which of the following reaction conditions would result in anti-Markovnikov
addition to an alkene?
A) H2O/H+
B) HBr
C) HCl
D) [1] BH3; [2] H2O2/OH–
13. Which of the following alkenes will react fastest with water in the presence of a
small amount of H2SO4?
A) A B) B C) C D) D E) E
14. In which of the following alkene addition reactions will carbocation rearrangements
occur?
A) The addition of Br2 and H2O; halohydrin formation
B) The addition of Br2
C) The addition of H2O in the presence of acid
D) Reactions (The addition of Br2 and H2O; halohydrin formation) and (The addition of
H2O in the presence of acid) will both show carbocation rearrangements.
E) Reactions (The addition of Br2 and H2O; halohydrin formation), (The addition of Br2
), and (The addition of H2O in the presence of acid) will all show carbocation
rearrangements.
19. A compound M with molecular formula C8H12 and no triple bonds reacts with H2 to
give a new compound having molecular formula C8H14. What can be said about M?
A) M has 3 rings.
B) M has 2 rings and 1 bond.
C) M has 1 ring and 2 bonds.
D) M has 3 bonds.
E) It's impossible to say anything about the structure of M given this data.
A) A B) B C) C
A) A B) B C) C D) D E) E
A) A B) B C) C
24. Predict the product(s) of the following reaction.
A) A D) D
B) B E) E
C) C F) F
A) A D) D
B) B E) E
C) C F) F
A) A B) B C) C D) D
A) A D) D
B) B E) E
C) C F) F
A) A D) B and C
B) B E) A, B, C and D
C) A and D
31. Consider the reaction below and determine which of the following statements is true.
A) The primary alcohol is formed since this type of reaction always leads to the
Markovnikov product.
B) The secondary alcohol is formed since this type of reaction always leads to the
Markovnikov product.
C) The primary alcohol is formed since this type of reaction always leads to the anti-
Markovnikov product.
D) The secondary alcohol is formed since this type of reaction always leads to the anti-
Markovnikov product.
E) A mixture of primary, secondary and tertiary alcohols products are formed.
A) A B) B C) C D) D
A) A B) B C) C
A) A D) B and C
B) B E) A, B, C and D
C) A and D
36. Which of the following could be used to prepare the following alkyl halide?
A) A B) B C) C D) D E) E
37. The only possible starting material for the reaction below is 2-methyl propene.
A) True B) False
38. What is the starting material in the reaction below?
A) A B) B C) C
A) Br2/CCl4
B) [1] BH3, [2] H2O2/OH–
C) 9-BBN
D) NBS
E) [1]Br2, [2] H2O
A) Br2/CCl4
B) [1] BH3, [2] H2O2/OH–
C) 9-BBN
D) NBS
E) [1]Br2, [2] H2O
41. From the list of possible carbocations, which one would not be likely to rearrange?
A) A B) B C) C D) D E) E
42. Each of the following compounds will be subjected to complete combustion. If one
mole of each compound is used, which one will liberate the most heat?
A) 1-pentene
B) 2-pentene
C) 3-methyl-1-butene
D) 2-methyl-1-butene
E) 2-methyl-2-butene
43. You are to synthesize 1-butene from 2-bromobutane. You must get the highest yield
possible. From the list of reagents given below, which one would you use to obtain
the greatest yield?
A) Alcoholic KOH
B) KOH and water
C) t-Butyl alcohol and (CH3CH2)3COK
D) Ethanol and CH3CH2ONa
E) Methanol and CH3ONa
44. What is the initial mechanistic step for the addition of HCl to propene?
A) initial attack by a chloride ion
B) initial attack by a chlorine atom
C) isomerization of 1-chloropropane
D) formation of a 1° carbocation
E) formation of a 2° carbocation
Challenge Questions
48. Dienes undergo many of the same types of reactions as alkenes. Consider the
mechanism for a Markovnikov addition of HBr to the following diene and predict
the major product.
A) A B) B C) C D) D E) E
49. (-)-Callystatin A (1) was isolated in 1997 from the marine sponge Callyspongia
truncata and exhibits potent cytotoxicity. Determine the stereochemistry of the
selected C=C bonds and stereocenters.
50. The reaction below is one of the steps used in the synthesis of (+/-)-
Perhydrohistrionicotoxin by Coote and co-workers. Predict which of the following
sets of reagents could be used for this transformation.
A) A B) B C) C D) D
51. Determine the structure of the final product when 3-carene is subjected to the
following reaction conditions.
A) A B) B C) C D) D
1. C
2. D
3. E
4. A
5. D
6. C
7. B
8. C
9. D
10. C
11. B
12. D
13. E
14. C
15. E
16. A
17. D
18. E
19. B
20. B
21. A
22. E
23. C
24. F
25. E
26. F
27. C
28. B
29. F
30. D
31. C
32. D
33. D
34. B
35. D
36. A
37. A
38. B
39. B
40. A
41. C
42. E
43. C
44. E
45. B
46. A
47. D
48. E
49. A
50. C
51. C
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Toisten maiden kuninkaat ja päälliköt tekivät vierailumatkoja ja
toivat lahjoja. Näistä ei Ochorin Bosambo ollut merkityksettömin.
— Herra Bosambo, sanoi hän, — jos jätät minut nyt, niin tulee
pimeä eikä ole aurinkoa. Sillä usein olen neuvonantajilleni puhunut
sinusta ja sinun teoistasi. Viivy sen vuoksi kanssani hetki, jotta voin
juoda sinun ymmärryksestäsi.
Tämä täytyi tehdä pimeässä, sillä jos sattumalta ovi tai ikkuna on
auki valon aikana, niin varmasti hytti on täynnä pieniä metsän veljiä,
satalajisia kärpäsiä, siivekkäitä koppakuoriaisia ja aivan varmaan
moskiitteja — jotka levittävät kuumetta. Pitkän harjaannuksen
totuttamana Sandersin käsi kosketti kolmea ikkunaa, tapasi salvat
paikallaan ja lukittuina.
— Mene takaisin samaa tietä, jota tulit, sanoi hän ja seurasi varjoa
laivalle.
Sanders huomasi yökulkijan hieman poikaa suuremmaksi ja
kävelevän tavalla, joka antoi aihetta luuloon, että hän oli tyttö.
Tyttö hymyili.
Sanders nyökkäsi.
— Vien sinut pois, sanoi hän, — koska olet yrittänyt tappaa minut
asettamalla myrkytettyjä okaita vuoteeseeni.
— Medini, minun naiseni, teki sen rakkaudesta minuun, sanoi
kuningatar, — ja jos hän sanoo minun häntä siihen käskeneen, niin
hän valehtelee.
Sellaisiksi ne osoittautuivat.
— Sillä niin kuin tiedät, herra, minun isäni ja hänen isänsä olivat
tämän alueen päällikköjä, ja minun suonissani virtaa kuninkaallinen
veri.