Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

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Student: ___________________________________________________________________________

1. Which of the following compounds shows conjugation?

A. A
B. B
C. C
D. D
E. E

2. Which of the following is conjugated?

A. A
B. B
C. C
D. D
E. E

3. Which of the following contribute to more stable resonance structures?

A. Fewer charges
B. Negative charges on more electronegative atoms
C. Negative charges on more electropositive atoms
D. Fewer charges and negative charges on more electronegative atoms
E. Fewer charges and negative charges on more electropositive atoms

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

4. What is the hybridization of the labeled atom?

A. sp3
B. sp2
C. sp
D. p

5. What is the hybridization of the labeled atom?

A. sp3
B. sp2
C. sp
D. p

6. Which of the following can be an S-cis diene?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

7. Which of the following is the most reactive diene in the Diels-Alder reaction?

A. A
B. B
C. C
D. D

8. Which of the following is the most reactive dienophile in the Diels-Alder reaction?

A. A
B. B
C. C
D. D

9. Which of the following is an example of a bridged bicyclic system?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

10. Which of the following is a resonance structure for the following anion?

A. A
B. B
C. C
D. D
E. E

11. Which of the following cations is not a resonance structure for the compound below?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

12. Which is the best resonance structure?

A. A
B. B
C. C

13. Which of the following is not a reasonable resonance structure for the anion below?

A. A
B. B
C. C

14. What is the product?

A. A
B. B
C. C

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

15. What is the product?

A. A
B. B
C. C
D. D

16. What is the product?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

17. What is the product?

A. A
B. B
C. C
D. D

18. What orbitals are used to form the indicated bond?

A. sp3
B. sp2
C. p
D. sp3 and sp2
E. sp2 and p
F. sp3 and p

19. What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

20. What is the correct structure for para-bromotoluene?

A. A
B. B
C. C
D. D

21. Is the following compound aromatic?

A. Yes
B. No

22. Which of the following compounds is not aromatic?

A. A
B. B
C. C
D. D

23. Which of the following compounds is not aromatic?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

24. Which of the following compounds is aromatic?

A. A
B. B
C. C
D. D

25. Why is the following compound not aromatic?

A. It has 4n electrons
B. It isn't planar
C. It has 4n+2 electrons
D. The electron system is not continuous

26. Why is the following compound not aromatic?

A. It has 4n electrons
B. It isn't planar
C. It has 4n+2 electrons
D. The electron system is not continuous

27. What is the IUPAC name for the following compound?

A. meta-chlorophenol
B. para-chlorophenol
C. 2-hydroxychlorobenzene
D. 2-chlorophenol

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

28. Which of the following compounds is/are aromatic?

A. A
B. B
C. C
D. D
E. E
F. F

29. What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?

A. To neutralize the base that is present

B. To make room for the electrophile
C. To make the ring more reactive
D. To reform an aromatic system

30. What is the electrophile in aromatic nitration?

A. NO+
B. NO2+
C. NO3+
D. NO2H

31. What is the electrophile in aromatic sulfonation?

A. H2SO3
B. H2SO4
C. SO3+
D. HSO3+

32. What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic
substitution?

A. Steric and electronic

B. Inductive and steric
C. Inductive and resonance
D. Resonance and electronic

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

33. What will be the site that leads to the major product for an electrophilic substitution reaction?

A. A
B. B
C. C
D. D

34. What reagent would you use for the following reaction?

A. Br2, FeBr3
B. NBS, light
C. CH2Br2, AlBr3
D. AlBr3

35. What is the product?

A. A
B. B
C. C
D. D

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

36. What is the product?

A. A
B. B
C. C
D. D

37. What is the missing reagent in the reaction below?

A. H2SO4
B. HNO3
C. HNO3, H2SO4
D. HNO2

38. What is the missing reagent in the reaction below?

A. Zn, HCl
B. PropylBr, AlCl3
C. NaBH4
D. H2, Pd/C

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

39. What was the starting material in the reaction below?

A. A
B. B
C. C
D. D

40. What is the missing reagent in the reaction below?

A. NBS
B. Br2, FeBr3
C. Br2, light
D. PdBr2

41. What is the missing reagent in the reaction below?

A. NaBH4
B. H2NNH2, KOH
C. H2, Pd/C
D. KMnO4

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

42. Which of the following statements is (are) true about electrophilic aromatic substitution?

A. OCH3 is an o, p activator because of a strong electron donating resonance effect.

B. OCH3 is an o, p director because of a strong electron withdrawing inductive effect.
C. OCH3 is an o, p activator because the O atom is an electronegative atom.
D. Both statements (OCH3 is an o, p activator because of a strong electron donating resonance effect) and (OCH 3 is an o, p
activator because the O atom is an electronegative atom) are true.
E. Statements (OCH3 is an o, p activator because of a strong electron donating resonance effect), (OCH3 is an o, p director
because of a strong electron withdrawing inductive effect), and (OCH 3 is an o, p activator because the O atom is an
electronegative atom) are all true statements.

43. Rank the following compounds in order of increasing reactivity towards electrophilic aromatic substitution.

A. A < B < C
B. A < C < B
C. C < B < A
D. B < C < A
E. C < A < B

44. Which of the following statements is (are) true about electrophilic aromatic substitution on a benzene ring with a chlorine
atom as substituent?

A. Cl is an o, p director because of an electron donating resonance effect.

B. Cl is a deactivator because of an electron withdrawing inductive effect.
C. Cl is a deactivator because the Cl atom is an electronegative atom.
D. Both statements (Cl is an o, p director because of an electron donating resonance effect) and (Cl is a deactivator because of
an electron withdrawing inductive effect) are true.
E. Statements (Cl is an o, p director because of an electron donating resonance effect), (Cl is a deactivator because of an
electron withdrawing inductive effect), and (Cl is a deactivator because the Cl atom is an electronegative atom) are all true
statements.

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18

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Collymore-Chalmers Chemistry 207

Practice Set 3 Chapters 16, 17 & 18