University of North Florida

CHM 2211

CHAPTER 23 AMINES

MULTIPLE CHOICE

1)Which of the following compounds are primary (1?) amines?

1. 1. 1 and 2
   2. 1 and 3
   3. 1, 2 and 3

d. 1, 2, 3 and 4

2. Which of the following compounds are secondary (2?) amines?

1. (CH₃)₃CNHCH₃
2. CH₃CH(NH₂)CH₂CH₃
3. CH₃CH₂CH₂NHCH₃
4. CH₃CH₂CH₂CH₂CH₂NH₂

1. 1 and 2
2. 1 and 3
3. 1, 2 and 3

d. 1, 2, 3 and 4

3. Which of the following compounds are tertiary (3?) amines?

1.        (CH₃)₂CHN(CH₃)₂

1. 2. CH₃CH(CH₃)N(CH₂CH₃)₂
   3. CH₃CH₂CH₂NHCH₃
   4. CH₃CH₂CH₂CH₂CH₂NH₂

1. 1 and 2
2. 1 and 3
3. 1, 2 and 3

d. 1, 2, 3 and 4

4. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

1. 1 = amide; 2 = 2 amine; 3 = oxime
2. 1 = imine; 2 = oxime; 3 = hydrazone
3. 1 = 2? amine; 2 = oxime; 3 = hydrazine
4. 1 = imine; 2 = hydrazone; 3 = 2? amine

5. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

1. 1 = imine; 2 = hydrazone; 3 = amide
2. 1 = 2? amine; 2 = amide; 3 = hydrazone
3. 1 =oxime; 2 = hydrazone; 3 = nitrile
4. 1 = amide; 2 = nitrile; 3 = hydrazone

6. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

1. 1 = 2? amine; 2 = enamine; 3 = hydrazine
2. 1 = 2? amine; 2 = amide; 3 = nitrile
3. 1 =oxime; 2 = hydrazone; 3 = nitrile
4. 1 = imine; 2 = hydrazone; 3 = amide

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

1. (R)-4-amino-2-methylhexane
2. (S)-4-amino-2-methylhexane
3. N-ethyl N-(3-methylpropyl) amine
4. (R)-3-amino-5-methylhexane

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

1. (E)-1-amino-4-hexene
2. (E)-6-amino-2-hexene
3. 3-allyl 1-aminopropane
4. (Z)-1-amino-2-hexene

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

1. (3R,4S)-3-amino-4-methylcyclohexene
2. (3R,4R)-3-amino-4-methylcyclohexene
3. (4R,5S)-5-amino-4-methylcyclohexene
4. (4R,5R)-5-amino-4-methylcyclohexene

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

1. 1-aminobicyclo[2.2.2]octane
2. 2-aminobicyclo[2.2.2]octane
3. 4-aminobicyclo[2.2.2]octane
4. 2-aminobicyclo[6.4.4]octane

11. What is the approximate pK_a value of (CH₃)₃NH⁺, the conjugate acid of trimethylamine?

1. ?2
2. 5
3. 10
4. 25

12. Which of the following is the strongest base?

1. ammonia
2. dimethylamine
3. aniline
4. 4-nitroaniline

13. Which of the following is the weakest base?

1. 4-methylaniline
2. 4-nitroaniline
3. aniline
4. 4-chloroaniline

14. Which of the following is the weakest base?

1. aniline
2. 3-nitroaniline
3. 4-nitroaniline
4. 4-methoxyaniline

15. Which of the following is the strongest base?

1. phenol
2. aniline
3. methylamine
4. 4-nitroaniline

16. Which of the following will remove aniline from a solution of aniline in diethyl ether?

1. aqueous KBr
2. aqueous HCl
3. aqueous NaOH
4. aqueous CH₃COONa

17. What is the correct assignment of the names of the following aromatic compounds?

1. 1 = anisole; 2 = furan; 3 = pyrimidine
2. 1 = aniline; 2 = pyrrole; 3 = pyridine
3. 1 = anisole; 2 = pyridine; 3 = pyrrole
4. 1 = aniline; 2 = imidazole; 3 = pyridine

18. What is the hybridization of the nitrogen atom of pyridine?

1. s
2. sp
3. sp²
4. sp³

19. What is the hybridization of the nitrogen atoms labeled i and ii in the aromatic imidazole ring?

1. i = sp^2;; ii = sp²
2. i = sp²; ii = sp³
3. i = sp³; ii = sp³
4. i = sp³; ii = sp²

20. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

21. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

22. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

23. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

24. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

25. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

26. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

27. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

28. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

29. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

30. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

31. 
    What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

32. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

33. What is the major organic product obtained from the following reaction?

1. 1
2. 2
3. 3
4. 4

34. What is the intermediate in the Hofmann elimination, in which a 1? or 2? alkyl halide is treated with trimethyl amine, followed by addition of silver(I) oxide and heat?

1. a tetraalkylammonium hydroxide salt
2. a tertiary amine
3. a 3? carbocation
4. an amine oxide

35. What is the intermediate in the Cope elimination, in which a 3? amine is treated with hydrogen peroxide followed by heat?

1. a tetraalkylammonium hydroxide salt
2. an amine oxide
3. a 3? carbocation
4. an amide anion

36. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

37. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

38. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

39. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

40. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

41. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

42. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

43. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

44. What is the major organic product obtained from the following sequence of reactions?

1. 1
2. 2
3. 3
4. 4

45. Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

1. only 1
2. only 3
3. only 1 and 3
4. only 2 and 4

46. Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

1. only 1
2. only 3
3. only 1 and 3
4. only 2 and 4

47. Which of the following amines can be prepared from an organic bromide reaction with potassium cyanide followed by reduction?

1. 1-heptanamine
2. benzylamine
3. 2-butanamine
4. tert-butyl amine

48. Which of the following amines can be prepared from an organic bromide by reaction with sodium azide followed by reduction?

1. aniline
2. benzylamine
3. N-ethyl-2-butanamine
4. tert-butyl amine

49. Which of the following amines can be prepared by reduction of an amide?

1. tert-butyl amine
2. 2-hexanamine
3. N-methyl-1-butanamine
4. aniline

50. Which of the following amines can be prepared by ring opening of an epoxide with sodium amide followed by reduction?

1. only 1
2. only 1 and 2
3. only 1 and 4

d. 1, 2, 3 and 4

51. Which of the following amines can be prepared by treatment of a carbonyl compound with sodium cyanide in the presence of acid, followed by reduction?

1. only 1
2. only 1 and 2
3. only 1, 2 and 3

d. 1, 2, 3 and 4

PROBLEM

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

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

3. Provide a line-bond structure of N,N-dimethylcyclopentanamine.

4. Provide a line-bond structure of N-methylaniline.

5. Provide a brief explanation, based on features of the molecules, for the following difference in pK_a values?

CH₃NH₂   >        NH₃ 10.64                    9.26

6. Provide a brief explanation, based on features of the molecules, for the following difference in pK_a values?

CH₃NH₂   >        PhNH₂ 10.64                        4.63

7. Provide a brief explanation, based on features of the molecules, for the following trend in pK_a values?

4.15                                                                               4.63

1.0

8. What is the major organic product obtained from the following reaction?

9. What is the major organic product obtained from the following sequence of reactions?

10. What is the major organic product obtained from the following sequence of reactions?

11. What is the major organic product obtained from the following sequence of reactions?

12. What is the major organic product obtained from the following sequence of reactions?

13. What is the major organic product obtained from the following sequence of reactions?

14. What is the major organic product obtained from the following sequence of reactions?

15. What is the major organic product obtained form the following sequence of reactions?

16. What is the major organic product obtained form the following sequence of reactions?

17. What is the major organic product obtained from the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

18. What is the major organic product obtained from the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

19. What is the major organic product obtained form the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?