Exam Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) In the mass spectrum of dipropylamine, the base peak appears at m/z:
A) 86
B) 101
C) 58
D) 72
E) none of the above
1)
2) Which of the following is not an alkaloid?
A) morphine
B) mesitylene
C) cocaine
D) nicotine
E) mescaline
2)
3) The nitrogenʹs lone pair in pyrrolidine is best described as occupying what type of orbital?
A) sp
B) sp3
C) s
D) sp2
E) p
3)
4) Which of the following amines can be resolved into enantiomers?
A) dimethylammonium chloride
B) 3-pentanamine
C) trimethylamine
D) 4-(dimethylamino) pyridine
E) 2-pentanamine
4)
5) Heating a(n) __________ results in a Cope elimination.
A) amine oxide
B) imine
C) oxime
D) quaternary ammonium salt
E) enamine
5)
6) A three-carbon, nitrogen-containing compound exhibits 3 13C NMR peaks (d 11.2, 27.3, and 44.9).
Which of the following compounds best matches this spectral data?
A) CH3 NHCH2 CH3
6)
B) CH3 CH2 C≡N
C) H2 NCH2 CH2 CH2 OH
D) (CH3 )2 CHNH2
E) CH3 CH2 CH2 NH2
7) When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:
A) 3-aminopyridine
B) 3-nitropyridine
C) 2-nitropyridine
D) 4-nitropyridine
E) 4-aminopyridine
1
7)
8) Sec-Butylamine is the common name of what compound?
A) 2-butanamine
B) N-methyl-2-propanamine
C) N-methyl-1-propanamine
D) N-ethylethanamine
E) 1-butanamine
8)
9) When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution
occur?
A) 3-position
B) 2-position
C) 4-position
9)
10)
10) Which of the following compounds is a 2° amine?
A) cyclohexylamine
B) N-ethylaniline
C) N-butylpyridinium bromide
D) N,N-diethylaniline
E) t-butylamine
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
11) Compound A, C9 H17N, is an optically inactive alkaloid, containing a tertiary amine that
11)
is not located at the bridgehead of the structures fused bicyclic ring system. Exhaustive
alkylation of A with methyl iodide, followed by a Hofmann elimination reaction resulted
in a racemic mixture of chiral tertiary amine products B, C10H19N. Provide a structure
for A and one of the enantiomeric products B.
12) The final product is a derivative of Amonafide, a drug used to treat breast cancer ( J. Med.
Chem. 2007, 4122). Complete each step of the synthesis by filling in the necessary reagents.
12)
13) Provide the structure of 2,4-dimethylpyridine
13)
14) Provide the structure of the major organic product in the reaction below.
14)
15) Draw the structure of N-ethyl-N-methyl-1-hexanamine.
15)
2
16) Provide the major organic product of the following reaction.
16)
17) Provide the major organic compound in the following reaction.
17)
18) Provide the structure of N-ethyl-1-butanamine.
18)
19) Arrange the following compounds in order of increasing boiling point: ethyl methyl ether,
1-propanol, N-methylethanamine, and 1-propanamine.
19)
20) Provide the name of (CH3 CH2 )4 N+ Cl- .
20)
21) Provide the structure of the major organic product in the reaction below.
21)
22) Provide the structure of the major organic product in the reaction below.
22)
23) Complete the short synthesis below by providing the necessary reagents.
23)
3
24) Circle all of the following structures that can be resolved into pure enantiomers.
24)
25) Arrange the following compounds in order of increasing boiling point:
25)
CH3 NHCH2 CH3 , CH 3 OCH2 CH3 , (CH3 )3 N, and CH3 CH2 CH2 OH.
26) Provide the formula for nitrous acid.
26)
27) Provide the major organic product of the following reaction.
27)
28) Provide the major organic product of the following reaction.
28)
29) Provide the major organic product of the following reaction.
29)
30) Complete the following reaction by filling in the necessary reagents.
30)
4
31) Provide the major organic product of the following reaction.
31)
32) Provide the IUPAC name of (CH 3 )3 CCH2 CH2 NHCH2 CH3 .
32)
33) Provide the major organic compound in the following reaction.
33)
34) Provide the major organic product of the following reaction.
34)
35) If ethanol has a pKa value of 16, what is the pKb value of the ethoxide anion?
35)
36) Provide the IUPAC name for the compound shown below.
36)
37) Arrange the following in order of increasing basicity: aniline, p-nitroaniline, p-toluidine,
and p-methoxyaniline.
37)
38) What sequence of reagents can be used to carry out the transformation shown below?
38)
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39) Provide the name of the compound shown below.
39)
40) Devise an efficient method for preparing fluorobenzene from benzene.
40)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
41) Draw the structure of piperidine.
42) Provide the structure of the major organic product in the reaction below.
43) Can 2-methyl-2-butanamine be prepared in good yield from the reaction of ammonia with
2-bromo-2-methylbutane? Why or why not?
44) Provide the product of the reaction shown below.
45) Why canʹt N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is
chiral?
46) Devise an efficient method for preparing 4-bromobenzonitrile from benzene.
47) Devise an efficient method for preparing 1-pentanamine from 1-chloropentane.
48) Why are strongly acidic reagents inappropriate when attempting an electrophilic aromatic substitution with
aniline?
49) Provide the structure of the major organic product in the reaction below.
50) Devise an efficient method for preparing 2-phenylethanamine from 2-phenylethanol.
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Answer Key
Testname: 12B‐AMINES
1) D
2) B
3) B
4) E
5) A
6) E
7) B
8) A
9) B
10) B
11)
12)
13)
14)
15)
7
Answer Key
Testname: 12B‐AMINES
16)
17)
18) CH3 CH2 CH2 CH2 NHCH2 CH3
19) ethyl methyl ether < N-methylethanamine < 1-propanamine < 1-propanol
20) tetraethylammonium chloride
21)
22)
23) 1) NaNO 2 / HCl 2) CuCN 3) LiAlH 4 or H 2 / Pd
24)
25) (CH3 )3 N < CH 3 OCH2 CH3 < CH 3 NHCH2 CH3 < CH 3 CH2 CH2 OH
26) HNO2
27)
28)
8
Answer Key
Testname: 12B‐AMINES
29)
30)
31)
32) N-ethyl-3,3-dimethyl-1-butanamine
33)
34)
35) -2
36) 3,3-dimethyl-1-butanamine
37) p-nitroaniline < aniline < p-toluidine < p-methoxyaniline
38) 1. NaNO2 , HCl 2. CuBr
39) 6-amino-1-methylcyclohexene
40) 1. HNO3 , H2 SO4
2. Fe, HCl
3. - OH
4. NaNO 2 , HCl
5. HBF4
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Answer Key
Testname: 12B‐AMINES
41)
42)
43) No. SN2 reactions do not proceed with tertiary substrates.
44)
45) Enantiomers interconvert rapidly via nitrogen inversion.
46) 1. Br2 , FeBr3
2. HNO3 , H2 SO4
3. Sn, HCl
4. H2 SO4 , NaNO2
5. CuCN
47) 1. phthalimide anion
2. H2 NNH2 , heat
or
1. NaN3
2. LiAlH 4 or H 2 , Pd
48) Acidic reagents protonate the amino group transforming it from an activating group to a deactivating group.
49)
50) 1. PCC
2. H2 NOH
3. H2 , Ni or LiAlH4
or
1. SOCl2
2. NaN3
3. LiAlH 4 or H 2 , Pd
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