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ACS Review 22 Amines

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ACS Review Amines

1. What is an acceptable name of the following compound?

CH3CH2CH2CH2NHCH3
A. N-methylbutylamine
B. 1-methyl-1-butylamine
C. N-butylmethylamine
D. 2-pentylamine
2. What is the IUPAC name of the following compound?

A. 2-methyl-4-hexanamine
B. 2-methyl-4-aminohexane
C. 5-methyl-3-hexanamine
D. 5-methyl-3-aminohexane
3. Which of the following is the correct IUPAC name of the compound shown below?

A. 1,2-dichloro-4-(N,N-dimethyl)aniline
B. dimethyl-(3,4-dichlorophenyl)amine
C. 3,4-dichloro-N,N-dimethylaniline
D. N,N-dimethylamino-3,4-dichlorobenzene
4. Which one of the following is ethyl 4-(dimethylamino) butanoate?

A. A
B. B
C. C
D. D
5. Among the isomeric C4H11N amines below, the one with the lowest boiling point is:
A. CH3CH2CH2CH2NH2
B. (CH3CH2)2NH
C. (CH3)2CHNHCH3
D. (CH3)2NCH2CH3
6. Rank the following three compounds in order of decreasing basicity.

A. I > II > III


B. II > I > III
C. III > II > I
D. III > I > II
7. Rank the following three compounds in order of decreasing acidity.

A. II > III > I


B. II > I > III
C. III > I > II
D. III > II > I
8. In the following two-phase reaction, the catalyst works by:

A. transferring CN¯ from the aqueous phase to the organic phase containing C6H5CH2Br.
B. transferring C6H5CH2Br from the organic phase to the aqueous phase containing CN¯ .
C. removing Br¯ from the organic phase to the aqueous phase.
D. removing K+ from the organic phase to make cyanide ion more nucleophilic.
9. Which one of the following is not a resonance form of para-aminobenzaldehyde?
A. I
B. II
C. III
D. IV
10. To convert a nitrile to a primary amine you must:
A. hydrolyze it with water
B. oxidize it with chromic acid
C. reduce it with hydrogen or lithium aluminum hydride
D. substitute it with an alkyl halide
11. Which one of the following is the strongest base?

A. A
B. B
C. C
D. D
12. Which of the following is the product of the reaction shown below?

A. (CH3)2CHCH2CH2NHNH2
B. (CH3)2CHCH2CH2NH2
C. [(CH3)2CHCH2CH2]2NH
D. (CH3)2CHCH2CH2CONH2
13. Which pair of reagents would be used to make the following amine by reductive amination?

A. methylamine and 2-methylbutanoic acid


B. methylamine and 2-methylbutanal
C. ammonia and 3-methyl-2-pentanone
D. dimethylamine and 2-butanone
14. Which of the following reagents can convert cyclohexanone to N-ethylcyclohexylamine as shown below?

A. CH3CH2NH2 and H2/Pt


B. LiAlH4 followed by H2O and then CH3CH2Br
C. CH3CH2Br and NH3
D. CH3CH=O and NH3
15. Which one of the following compounds gives propylamine, CH3CH2CH2NH2, upon hydrolysis?

A. A
B. B
C. C
D. D
16. Rank the following three compounds in decreasing order of basicity.

A. III > I > II


B. III > II > I
C. II > I > III
D. II > III > I
17. Which one of the following does not give N-ethylcyclopentylamine as the major product?

A. A
B. B
C. C
D. D
18. Which one of the following synthetic routes gives the best yield of meta-bromoaniline starting with
benzene?
A. A
B. B
C. C
D. D
19. Which one of the following amines gives an N-nitrosoamine on treatment with nitrous acid, HNO2?
A. 2,4-dimethylaniline
B. 3,5-dimethyaniline
C. N,4-dimethylaniline
D. N,N-dimethylaniline
20. What is the product of the following reaction?

A. 3,5-dimethyl-4-nitrophenol
B. 1,3-dimethyl-5-nitrobenzene
C. meta-xylene (meta-dimethybenzene)
D. 3,5-dimethylphenol
21. Which of the following is the product of the reaction sequence shown below?

A. meta-bromochlorobenzene
B. 1,3,5-tribromobenzene
C. 1,3-dibromo-5-chlorobenzene
D. mixture of ortho and para-bromochlorobenzene
22. Which of the following would be the starting reagents needed to make the azo compound shown below?
A. A
B. B
C. p-ethylaniline + phenol
D. aniline + p-ethylphenol
23. Reaction of an N,N-dialkylaniline with nitrous acid yields:
A. a diazonium salt
B. a para-nitroso compound
C. an N-nitroso compound
D. an azo compound
24. What is the product of the reaction series shown below?

A. I
B. II
C. III
D. IV
25. What is the major product of the reaction sequence below?

A. A
B. B
C. C
D. D
26. Which one of the following forms a diazonium ion on being treated with NaNO2 in aqueous HCl?
A. para-nitrotoluene
B. ethylamine
C. N,N-dimethylaniline
D. triethylamine
27. What is the product of the following reaction?

A. 1-amino-2-methylpropane
B. 2-amino-2-methylpropane
C. isopropylamine
D. tert-butylamine
28. Which of the following is a tertiary amine?
A. CH3CH2CH2NH2
B. CH3CH2NHCH3
C. (CH3)3N
D. (CH3)3CNH2
29. The following compound is classified as a(n):
A. amide
B. primary amine
C. secondary amine
D. tertiary amine
30. What is the mechanism of the following reaction?

A. SN1
B. SN2
C. free radical
D. electrophilic aromatic substitution
ACS Review Amines KEY
1. A
2. C
3. C
4. D
5. D
6. D
7. B
8. A
9. B
10. C
11. B
12. B
13. B
14. A
15. B
16. B
17. D
18. C
19. C
20. D
21. A
22. C
23. B
24. C
25. A
26. B
27. A
28. C
29. D
30. D

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