Douglas County High School, Minden

ORGO CHEM 1020

Chapter 11 -- Amines and Related Nitrogen Compounds

MULTIPLE CHOICE

1)Tert-butylamine is classified as a(n)                                    amine.

1. 1. 1°
   2. 2°
   3. 3°
   4. quaternary salt
   5. aromatic

2. Which of the following are tertiary amines?

1. 1. 1 and 3
   2. only 5

C) 1, 2, 3, and 4

4. 2 and 4
5. 1 and 2

3. The structure below can be named in the following manner:

1. 1. 2-nitrocyclohexanamine
   2. m-nitroaniline
   3. o-nitroaniline
   4. 2-nitrobenzylamine
   5. 1,2-diaminobenzene

4. The structure that corresponds to N-ethyl-2,3-dimethyl-3-hexanamine is
   1. 
      D)
   2. E)

5. Which of the following compounds is a tertiary amine?
   1. D)

1. 2. E)

C)

6. Which of the following molecules has the highest boiling point?
   1. ethylamine
   2. propane
   3. ethyl alcohol
   4. dimethyl ether
   5. acetaldehyde

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

aqueous HCl.

1. 3. extract the ether solution with water and treat the water layer with aqueous NaOH.
   4. extract the ether layer with aqueous HCl and treat the ether layer with aqueous NaOH.
   5. extract the ether solution with aqueous HCl and treat the ether layer with aqueous HCl.

8. Which of the following statements is false:
   1. Aliphatic 3^o amines with three different groups on nitrogen can be resolved.
   2. Primary and secondary aliphatic amines can be hydrogen bond donors.
   3. Aliphatic amines can be hydrogen bond acceptors.
   4. The non-bonded lone pair in an aliphatic amine is more basic than the non-bonded lone pairs in ethers.
   5. The nitrogen in aliphatic amines is sp³-hybridized.

9. Which compound is the strongest base?
   1. CH₃NH₂
   2. CH₃CO₂H
   3. CH₃CHO
   4. CH₃OH
   5. C₆H₅NH₂

10. Which of the following amines is the most basic?
    1. methylamine
    2. dimethylamine
    3. ammonia
    4. aniline
    5. N-methylaniline

11. The order of decreasing pK_as of the corresponding ammonium ions of the following is:

A) 1 > 2 > 3 > 4

B) 3 > 4 > 2 > 1

C) 4 > 3 > 2 > 1

D) 2 > 1 > 3 > 4

E)   4 > 3 > 1 > 2

12. The order of decreasing acidity of the following is:

A) 1 > 2 > 3

B) 3 > 1 > 2

C) 2 > 1 > 3

D) 3 > 2 > 1

E)   2 > 3 > 1

13. 
    The order of increasing basicity of the following is:

A) 1 < 2 < 3 < 4

B) 2 < 3 < 1 < 4

C) 4 < 3 < 2 < 1

D) 4 < 3 < 1 < 2

E)   4 < 1 < 3 < 2

14. When methylamine (CH₃NH₂) reacts with methyl bromide (CH₃Br) to give dimethylamine, the methylamine:
    1. acts as an electrophile
    2. acts as a Lewis acid
    3. acts as a Bronsted-Lowry acid
    4. acts as a Bronsted-Lowry base
    5. acts as a nucleophile in an S_N2 reaction

15. What is the mechanism for the intramolecular alkylation shown below?

1. 1. S_N2
   2. S_N1
   3. nucleophilic acyl substitution
   4. nucleophilic addition
   5. electrophilic addition

16. The mechanism by which acylation of an amine with an acid chloride takes place is:
    1. nucleophilic acyl substitution
    2. electrophilic aromatic substitution
    3. nucleophilic addition
    4. electrophilic addition
    5. nucleophilic aromatic substitution

17. The alkylation of an amine with an alkyl halide takes place by the following mechanism:
    1. S_N1
    2. S_N2
    3. electrophilic addition
    4. E1
    5. E2

18. What structure represents a cationic intermediate in the electrophilic aromatic bromination of aniline?

1. 1. I
   2. II
   3. III
   4. IV
   5. V

19. Which of the following is not an intermediate in the diazotization of aniline using nitrous acid?

1. 1. I
   2. II
   3. III
   4. IV
   5. none of the above

20. C₆H₅NHCH₂CH₂CH₃ can best be prepared as follows:

A)

B)

C)

D)

E)

21. Reacting aniline, C₆H₅NH₂, with a primary alkyl halide will produce a(n):
    1. 1° amine
    2. 2° amine
    3. 3° amine
    4. amide
    5. imine

22. An imine is produced when a ketone or aldehyde reacts with:
    1. methyl alcohol
    2. Zn(Hg), HCl
    3. an amine
    4. an amide
    5. HCN

23. What is the name of the product of the following reaction?

1. 1. chlorobenzene
   2. chloroaniline
   3. anilinium chloride
   4. o-chloroaniline
   5. N-chloroaniline

24. What is the stereochemical relationship of the products formed by reacting racemic lactic acid with (S)-1-phenylethylamine?
    1. enantiomers
    2. meso compounds
    3. racemic mixture
    4. diastereomers
    5. geometric isomers

25. Which of the following amines can be converted to an aryl diazonium salt?
    1. D)

1. 2. 
      E)

C)

26. Which molecule is known as an azo compound?

A)

B)

C)

D)

E)

27. What is the name of the product formed by reacting CuCl and HCl with benzenediazonium chloride?
    1. bromobenzene
    2. chlorobenzene
    3. o-chloroaniline
    4. m-chloroaniline
    5. p-chloroaniline

28. What reacts with benzenediazonium chloride to produce benzonitrile?
    1. HONO
    2. Li, NH₃
    3. NaBH₃CN
    4. KCN, Cu₂CN₂
    5. LiAlH₄, ether

29. What type of products are formed by diazo coupling reactions?
    1. meso compounds
    2. azo compounds
    3. diazonium salts
    4. quaternary ammonium salts
    5. racemic mixtures

30. Which reaction will produce a quaternary ammonium salt?

A)

B)

C)

D)

E)

31. What is the final product for the following sequence of reactions?

1. 1. 
      D)
   2. E)

32. Which of the following reaction sequences will convert p-bromoaniline to p-bromobenzoic acid?

1. 1. 1. NaNO₂, HCl 2. CH₃CO₂H
   2. 1. NaNO₂, HCl 2. Mg, ether 3. CO₂, H₃O⁺
   3. 1. CH₃Cl, AlCl₃ 2. KMnO₄
   4. 1. HCl 2. CH₃COCl 3. NaCN, H₃O⁺

1. 5. 1. NaNO₂, HCl 2. KCN, Cu₂CN₂ 3. H₃O⁺

33. 
    The following reaction sequence will produce:

1. 1. D)

1. 2. E)

C)

34. The product(s) of                                                                                                                     are:

A)

B)

D)

35. Aniline                                          is best prepared via:

A)

B)

C)

D)

E)

36. 
    The amines that can be acylated by acetic anhydride are

1. 1. only 4

B) 1, 2, 3, and 4

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

37. 
    The product(s) from the reaction below are:

A)

B)

C)

D)

E)

38. m-Dichlorobenzene can be prepared in good yield by the sequence:

B)

C)

E)

39. The product(s) from the reaction sequence below is (are):

A)

B)

C)

D)

E)

40. m-Chlorobromobenzene can be prepared in good yield by the sequence:

B)

C)

D)