University Of Arizona

CS 93

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 hybridization of the nitrogen atom of pyridine?

1. s
2. sp
3. sp²
4. sp³

18. 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

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

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

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 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

34. 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

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

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

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. 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

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 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

47. 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

48. 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

49. 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

50. 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

TRUE/FALSE

1. 
   The following structure is classified as a 3° amine.

2. To separate a mixture of p-toluidine and p-nitrotoluene dissolved in ether,extract the ether solution with aqueous HCl and treat the water layer with aqueous NaOH.

3. Aliphatic 3^o amines with three different groups on nitrogen can be resolved.

4. The following amine can be converted to an aryl diazonium salt.

5. 
   Consider the following reaction.

6. The reaction of a 2^o amine with nitrous acid gives a nitrosamine.

7. The following represents an acid-base reaction between the given amine and HCl.

8. 
   The pK_a of methyl amine is represented by the following reaction.

9. 
   The compound circled below represents a heterocyclic amine.

COMPLETION

Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term.

1. The ammonia ion of substance                 will have the largest pK_a.

2. The ammonia ion of substance                 will have the smallest pK_a.

3. Substance                is a primary alkyl amine.

4. The name of the product formed by reacting CuCl and HCl with benzenediazonium chloride is     .

5. The name of the product formed by reacting KCN and CuCN with benzenediazonium chloride is .

6. The IUPAC name of the product of the following reaction is                                                .

From the list provided below, choose the best reagent(s) for each step in the following synthesis. There is only one answer for each reaction. Enter the appropriate letter in the blank provided.

1. 1. NaBH₄ , ethanol                                                          d.     1.     NaNO₂ , H₃O⁺
   2. KCN, acetone                                                                      2.     CuCN, KCN
   3. 1.     LiAlH₄ , THF                                                            e.     1.     SnCl₂ , H₃O⁺

2.     H₂O                                                                                 2.     NaOH, H₂O

f.      HNO₃ , H₂SO₄

7.             Step 1
8.             Step 2
9.             Step 3

Consider the following substances.

Complete the following statements using the appropriate number.

10. Substance             is pyrrole.

11. Substance             is aniline.

12. Substance             is pyridine.

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?

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

values?

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

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 from the following sequence of reactions?

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