Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof.

Sivaguru Jayaraman

Chapter 5: Structure and Preparation of Alkenes –

Elimination Reactions
1. Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why?
A) The double bond is much stronger and thus more difficult to rotate.
B) Overlap of the two 2p orbitals of the π bond would be lost.
C) The shorter bond length of the double bond makes it more difficult for the
attached groups to pass each other.
D) Overlap of the sp2 orbitals of the carbon-carbon σ bond would be lost.
Ans: B

2. What is the IUPAC name of the following compound?

A) 2,5-dimethyl-1-hexene C) 2,5-dimethyl-2-hexene
B) 1,4-dimethyl-1-hexene D) 2,5-dimethyl-5-hexene
Ans: A

3. What is the IUPAC name of the following compound?

A) 2-methyl-3-propyl-2-pentene C) 4-ethyl-5-methyl-4-hexene
B) 3-ethyl-2-methyl-2-hexene D) 4-methyl-3-propyl-3-pentene
Ans: B

4. What is the IUPAC name of the following compound?

A) 3-ethyl-8-methyl-3-nonene C) 1,1-diethyl-6-methyl-3-heptene
B) 7-ethyl-2-methyl-6-nonene D) 3-ethyl-7-isopropyl-3-octene
Ans: A

5. How many isomeric alkenes of formula C4H8, including stereoisomers, are possible?
A) two B) three C) four D) five
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

6. How many isomeric alkenes of formula C5H10, including stereoisomers, are possible?
A) three B) four C) five D) six
Ans: D

7. What is the IUPAC name of the following compound?

A) 3-bromo-2-methylcyclohexene C) 6-bromo-1-methylcyclohexene
B) 1-bromo-2-methyl-2-cyclohexene D) 2-bromo-1-methylcyclohexene
Ans: C

8. What is the IUPAC name of the following compound?

A) 3-ethyl-propyl-1-heptene C) 4,6-diethyl-1-octene
B) ethyl-3-vinyloctane D) 3,5-diethyl-1-octene
Ans: D

9. Which of the following alkenes exhibit E-Z isomerism?

I. CH3CH2CH CHCH2CH3

II. (CH3)2C CHCH3

III. CH3CH2CH CHBr

IV. H2C CHCH2CH(CH3)2

A) I and II B) I and III C) II and IV D) I, II, and III
Ans: B

10. Which of the following alkenes exhibit E-Z isomerism?

I. 1-chloropropene II. 2-chloropropene III. 3-chloropropene
A) only I B) I and II C) II and III D) I and III
Ans: A

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

11. What is the IUPAC name of the following compound?

A) (E)-3-bromo-1-fluoro-2-methylpropene
B) (Z)-3-bromo-1-fluoro-2-methylpropene
C) (E)-1-bromo-3-fluoro-2-methylpropene
D) (Z)-1-bromo-3-fluoro-2-methylpropene
Ans: A

12. Which of the following C6H12 isomers has the highest heat of combustion?
A) 1-hexene B) trans-3-hexene C) cis-3-hexene D) 2-methyl-2-pentene
Ans: A

13. Identify the major organic product expected from the acid-catalyzed dehydration of 2-
methyl-2-pentanol.
A) 2-methyl-1-pentene C) 3-methyl-1-pentene
B) 2-methyl-2-pentene D) cis-3-methyl-2-pentene
Ans: B

14. Which alcohol below would undergo acid-catalyzed dehydration most readily?

A) A B) B C) C D) D
Ans: D

15. What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-
2-propanol?

A) Protonation of the alcohol to form an oxonium ion.

B) Loss of water from the oxonium ion to form a carbocation.
C) Loss of a β-hydrogen from the carbocation to form an alkene.
D) The simultaneous loss of a β-hydrogen and water from the oxonium ion.
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

16. Which of the following carbocations is(are) likely to undergo a rearrangement?

A) only I B) I and III C) II and III D) I, II, and III

Ans: D

17. Predict the major product of the following reaction.

A) A B) B C) C D) D
Ans: C

18. Which of the following expressions is the experimentally observed rate law for an E2
reaction of an alkyl halide?
A) rate = k[RX] B) rate = k[RX][base] C) rate = k[RX]2 D) rate = k[base]
Ans: B

19. Which of the following most readily undergoes an E2 reaction with sodium ethoxide
(NaOCH2CH3)?
A) (CH3)3CF B) (CH3)3CCl C) (CH3)3CBr D) (CH3)3CI
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

20. How many isomeric alkenes are possible, including stereoisomers, in the following
reaction?

A) two B) three C) four D) five

Ans: B

21. In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly

to the formation of cis-2-butene?

A) only I B) only II C) only III D) I and II

Ans: A

22. Which of the following cannot undergo an E2 reaction?

A) only I B) only II C) only III D) I and III

Ans: A

23. Which of the following would you predict to be the best method for doing the following
conversion with the highest yield?

A) H2SO4, heat B) NaOCH2CH3 C) H3PO4 D) (1) PBr3 (2) KOC(CH3)3

Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

24. When a strong base is used in the elimination reaction of an alkyl halide the mechanism,
in general, is
A) E1.
B) E2.
C) E1 for tertiary halides, E2 for primary and secondary halides.
D) E2 for tertiary halides, E1 for primary and secondary halides.
Ans: B

25. Which of the following sets of conditions most favors the E1 mechanism?
A) when the alkyl halide is tertiary and the base is a weak base
B) when the alkyl halide is tertiary and the base is a strong base
C) when the alkyl halide is primary or secondary and the base is a weak base
D) when the alkyl halide is primary or secondary and the base is a strong base
Ans: A

26. Which of the following would have the fastest rate of reaction to form 4-tert-
butylcyclohexene?

A) A B) B C) C D) D
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

27. What is the first step in the mechanism of the dehydration reaction of a tertiary alcohol
with sulfuric acid to form an alkene?
A) the loss of OH– to form a carbocation
B) the protonation of the hydroxyl group
C) the loss of the proton from the hydroxyl group to give an alkoxide ion
D) the removal of a β-hydrogen from the alcohol
Ans: B

28. Which of the following does not give 1,2-dimethylcyclohexene as one of the acid-
catalyzed dehydration products?

A) A B) B C) C D) D
Ans: D

29. Including E-Z isomers, how many E2 products are possible in the following reaction?

A) one B) two C) three D) four

Ans: C

30. Which of the following compounds gives a single E2 product on reaction with sodium
ethoxide, NaOCH2CH3?

A) I and II B) I and III C) II and III D) I, II, and III

Ans: B

Page 7 
Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

31. Which of the following will give 2-methyl-1-butene as the only alkene product on
treatment with KOC(CH3)3 in dimethyl sulfoxide?
A) 2-bromo-3-methylbutane C) 2-bromo-2-methylbutane
B) 1-bromo-3-methylbutane D) 1-bromo-2-methylbutane
Ans: D

32. If the following E2 reaction proceeds through an anti-periplanar transition state, what
product or products are expected?

CH3
KOC(CH3)3
(CH3)3COH
Cl
A) only 1-methylcyclohexene
B) only 3-methylcyclohexene
C) only 4-methylcyclohexene
D) equal amounts of 1-methylcyclohexene and 3-methylcyclohexene
Ans: B

33. Which of the following stereoisomers gives the exclusive E2 product shown?

A) A B) B C) C D) D
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

34. Zaitsev's rule can be used to predict the major product for which of the following
reactions?
A) 2-methylpentane + Br2(with light)
B) 2-bromo-2-methylpentane + NaOCH2CH3 (in ethanol)
C) 2-methyl-2-pentanol + PBr3
D) 2-methyl-2-pentanol + HCl
Ans: B

35. The acid-catalyzed dehydration of the alcohol shown below gives a major product
which results from a carbocation rearrangement. Identify this major product.

A) A B) B C) C D) D
Ans: A

36. Consider the following reaction.

R = –CH3 or –C(CH3)3
Which statement(s) below is(are) correct?
I. X is the major product based on Zaitsev's rule.
II. The X:Y ratio is greater when R = –CH3 than when R = –C(CH3)3.
III. The X:Y ratio is greater when R = –C(CH3)3 than when R = –CH3.
A) I and II B) I and III C) only II D) only III
Ans: A

37. How many different E2 products are expected in the reaction of 3-bromo-1,1-
dimethylcyclohexane with NaOCH2CH3?
A) only 1 B) 2 C) 3 D) 4
Ans: B

Page 9 
Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

38. Which one of the following compounds cannot undergo an E2 reaction?

A) 1-bromo-2,2-dimethylbutane C) 1-bromo-3,3-dimethylbutane
B) 1-bromo-2,3-dimethylbutane D) 2-bromo-2,3-dimethylbutane
Ans: A

39. What is the major product of the reaction sequence shown below?

A) 2-methyl-1-butene C) 3-methyl-1-butene
B) 2-methyl-2-butene D) 2-methylbutane
Ans: B

40. Which of the following compounds gives 4,4-dimethylcyclohexene as the exclusive E2

product?

A) A B) B C) C D) both A and B
Ans: A

41. How many stereoisomers are possible for the following diene?

CH3CH=CHCH2CH2CH=CHCH2CH2CH3
A) only 1 B) two C) three D) four
Ans: D

Page 10 
Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

42. Based on Zaitsev's rule, which of the following is the major product of the reaction
below?

A) A B) B C) C D) D
Ans: C

43. Which of the alkenes below has the Z-configuration?

H3CO CH3
A) CH3 B)
H3C OCH3
H
OCH3 CH3
H3C CH3
C) N D) Cl
CH3 CH3
H3C H3C
CH2CH3 OCH3
A) A B) B C) C D) D
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

44. Which alkene of formula C5H10 gives off the least heat (per mol) when burned?

A) B)

C) D)

A) A B) B C) C D) D
Ans: B

45. When a C=C is present in a molecule, what is the minimum number of atoms that must
lie in a single plane?
A) 2 B) 4 C) 6 D) 8
Ans: C

46. If you wanted to make compound III, starting with compound I or II, what would you
do?

OH
?
I

Br III
?

II
A) React I with H2SO4.
B) React II with NaOEt.
C) Either of the reactions in A or B above would work.
D) Neither of the reactions in A or B above would work.
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions: Answers Prof. Sivaguru Jayaraman

47. Which compound would react slowest with KOtBu?

Br Br
D D

A B
Br Br

D D
C D
A) A B) B C) C D) D
Ans: A

48. Which reagent accomplishes the following?

OH Cl
?

A) HCl B) Cl2, light C) SOCl2 D) NaCl

Ans: C

49. What would be the proper name of the molecule below?

A) (E)-2-ethyl-2-butene C) (E)-3-methyl-2-pentene
B) (Z)-3-methyl-3-pentene D) (Z)-2-isohexene
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.