Download 1. Absorption of what type electromagnetic radiation results in

1.
Absorption of what type electromagnetic radiation results in transitions among
allowed vibrational motions?.
A.
B.
C.
D.
E.
2.
X-rays
radio waves
microwaves
ultraviolet light
infrared light
Provide the reagents necessary for carrying out the transformation of
2-methylheptane to 2-methyl-2-heptene.
A.
H2SO4, heat
B.
1. Br2, h
2. NaOH
C.
1. Br2, h
2. NEt3
D.
1. H2O, H+
2. H2SO4,
heat
3.
Addition of Br2 to (Z)-3-hexene produces ____________________.
A.
B.
C.
D.
E.
a meso dibromide
a mixture of enantiomeric dibromides which is optically active
a mixture of enantiomeric dibromides which is optically inactive
(Z)-3,4-dibromo-3-hexene
(E)-3,4-dibromo-3-hexene
Page 1
4.
Which of the following best describes the carbon-chlorine bond of an alkyl
chloride?
A.
B.
C.
D.
E.
5.
nonpolar; no dipole
polar; δ+ at carbon and δ- at chlorine
polar; δ- at carbon and δ+ at chlorine
ionic
none of the above
An acid which could not be prepared from an organic halide by carboxylation of
the Grignard reagent is:
A.
B.
C.
D.
E.
6.
benzoic acid
2,2-dimethylpropanoic acid
propanoic acid
4-oxocyclohexanecarboxylic acid
2-methylbutanoic acid
Choose the correct hybridization for the atom indicated in the molecule below.
CH 3
C
C
C
H
H
CH 3
A.
sp
B.
sp2
sp3
C.
D.
none of the above
Page 2
7.
Classify the reaction below as an oxidation, a reduction, or neither.
(CH3)2CHCH2OH
A.
8.
oxidation
B.
(CH3)2CHCHO
reduction
C.
neither
How does the activation energy for the abstraction of a deuterium atom compare
to the activation energy for the abstraction of a hydrogen atom?
A.
B.
C.
D.
E.
9.
---------->
The activation energy for the abstraction of a deuterium atom is
higher.
The activation energy for the abstraction of a hydrogen atom is
higher.
The activation energies fro abstraction are identical since H and D
are isotopes.
There is no activation energy for abstraction of either a hydrogen
or a deuterium atom.
Not enough information to decide.
The reaction of LDA with acetophenone produces:
A.
B.
C.
D.
E.
an enol.
an enolate.
an ylide.
alkylation.
halogenation.
Page 3
Which of the following is a secondary alkyl halide?
A.
B.
C.
D.
E.
11.
The correct priority of functional groups in IUPAC nomenclature is:
A.
B.
C.
D.
E.
12.
methyl bromide
ethyl iodide
t-butyl iodide
isopropyl bromide
isobutyl chloride
ester > amide > ketone > acid.
ketone > acid > ester > amide.
acid > ester > amide > ketone.
amide > acid > ester > ketone.
amide > ester > acid > ketone.
Which of the following choices represent(s)a pair of resonance structures?
A.
O
CH 3 CH 2
B.
C
H
,
CH 3CH
CH
:
,
CH3CH
+
OCH 3
:
OCH 3
:
+
CH 3 CH
OH
C.
H
H
:
C
C
N :
10.
H
D.
E.
,
- :C
C
H
Both a and c
Both b and c
Page 4
N:
13.
14.
Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr
through essentially a(n) __________ mechanism.
A.
SN1
B.
SN2
C.
D.
E.
E1
E2
ring opening
1-Methylcyclopentanol is classified as _____________________.
A.
C.
15.
a primary alcohol
a tertiary alcohol
B.
D.
a secondary alcohol
none of the above
An ylide is a molecule that can be described as a:
A.
B.
C.
D.
E.
carbanion bound to a
carbocation bound to
carbocation bound to
carbocation bound to
carbanion bound to a
negatively charged heteroatom.
a negatively charged heteroatom.
a carbanion.
a diazonium ion.
positively charged heteroatom.
Page 5
16.
Rank the free radicals (I-III) shown below in order of decreasing stability (ie,
from most stable to least stable).
⋅ CH2CH 2CH(CH3)2
CH3CH2˙
C(CH3)2
CH3˙
CHCH(CH3)2
A.
B.
C.
D.
E.
17.
II
III
I > III > II
II > III > I
I > II > III
II > I > III
III > II > I
Secondary amines react with the nitrosonium ion to generate:
A.
B.
C.
D.
E.
18.
I
diazonium salts
N-nitrosoamines
oximes
imines
none of the above
The aldol condensation is:
A.
B.
C.
D.
E.
an irreversible reaction.
an equilibrium reaction.
a tautomerization.
an isomerization.
a type of esterification.
Page 6
19.
The first mechanistic step in the direct reaction of an amine with a carboxylic
acid to produce an amide is:
A.
B.
C.
an acid-base reaction
nucleophilic attack on the carbonyl carbon
loss of H2O
D.
loss of CO2
loss of N2
E.
20.
Which compound would be expected to show intense IR absorption at 1640 cm-1?
A.
C.
21.
1-hexene
CH3CH2CH2OH
B.
D.
2-methylheptane
CH3CH2COCH3
Which compound would be expected to show intense IR absorption at 3363, 3185,
1660 cm-1?
A.
CH3CH2CH2OH
B.
(CH3)2CHNH2
C.
CH3CH2CONH2
D.
1-butene
Page 7
22.
When ionization occurs at the single stereocenter of a chiral compound, the
resulting carbocation is:
A.
B.
C.
D.
E.
23.
chiral
achiral
racemic
optically active
none of the above
Which of the following best describes the geometry about the carbon-carbon
double bond in the alkene below?
CH3
Cl
A.
B.
C.
24.
E
Z
neither E nor Z
How many distinct nodal planes which are perpendicular to the molecular plane
are present in the π 5* orbital of benzene?
A.
0
B.
1
C.
2
Page 8
D.
4
E.
5
25.
In trans-4-hepten-2-yne the shortest carbon-carbon bond is between carbons
________________________.
A.
26.
B.
3 and 4
C.
4 and 5
D.
5 and 6
E.
6 and 7
Using Saytzeff's rule, choose the most stable alkene among the following.
A.
B.
C.
D.
27.
2 and 3
1-hexene
(E)-2-hexene
(Z)-2-hexene
They are all of equal stability according to Saytzeff's rule.
Which of the following describes a Rosenmund reduction?
A.
B.
hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned
catalyst
reaction of a primary alcohol with Na2Cr2O7
C.
D.
reaction of a ketone with ozone
treatment of an aldehyde with Sia2BH
E.
none of the above
Page 9
28.
Which of the following statements correctly describes the contribution of ∆S° to
∆G°?
A.
B.
C.
D.
E.
29.
∆G° at low
∆G° at high
∆G° in exothermic
∆G° in endothermic
contribution to
The hydrolysis of esters in base is called:
A.
B.
C.
D.
E.
30.
The entropy term makes a greater contribution to
temperatures.
The entropy term makes a greater contribution to
temperatures.
The entropy term makes a greater contribution to
reactions.
The entropy term makes a greater contribution to
reactions.
The entropy term always makes a more significant
∆G° than does the enthalpy term.
the Fischer esterification.
the Hunsdiecker reaction.
the Dieckmann condensation.
transesterification.
saponification.
An acid which could not be prepared by the reaction of an organic halide with
cyanide ion followed by acid hydrolysis of the nitrile is:
A.
B.
C.
D.
propanoic acid
phenylacetic acid
acetic acid
(CH3)3CCO2H
E.
CH3(CH2)14CO2H
Page 10
31.
In the mass spectrum of isobutylbenzene, the base peak occurs at m/z:
A.
32.
33.
134
B.
133
C.
119
D.
105
E.
91
Which compound will show an intense peak in the mass spectrum at m/z 58?
A.
CH3COCH2CH2CH3
B.
(CH3)2CHCOCH3
C.
CH3CH2COCH2CH3
D.
(CH3)3CCHO
E.
(CH3)3CCOCH3
What is the carbon nucleophile which attacks molecular bromine in the
acid-catalyzed α-bromination of a ketone?
A.
B.
C.
D.
E.
an enolate
a Grignard reagent
an acetylide
a carbocation
an enol
Page 11
34.
35.
The conjugate acid of ammonia, NH3, is:
A.
NH2-
B.
NH2OH
C.
NH4+
D.
none of the above
What is the product when cyclopentene is treated with Br2/H2O?
A.
C.
36.
cis-2-bromocyclopentanol
cis-1,2-dibromocyclopentane
B.
D.
trans-2-bromocyclopentanol
trans-1,2-dibromocyclopentane
The Hunsdiecker reaction converts silver n-butanoate into:
A.
B.
C.
D.
E.
1-bromobutane
1-bromopropane
2-bromobutane
2-bromopropane
ethyl bromide
Page 12
37.
Which of the following statements correctly describe(s) E1 reactions of alkyl
halides (RX)?
I.
II.
III.
IV.
V.
A.
B.
C.
D.
E.
38.
II and IV
III and V
I, IV, and V
I only
III, IV, and V
An _______ molecular ion peak usually indicates the presence of an odd number of
nitrogen atoms in the molecule.
A.
39.
Rate = k[base]
Rate = k[base][RX]
Rate = k[RX]
The reactions occur in two distinct steps.
Rearrangements are sometimes seen.
even
B.
odd
C.
intense
D.
avsent
Which functional groups below indicate the presence of two atoms connected by a
triple bond?
A.
B.
C.
D.
E.
F.
ether
alkyne
nitrile
alkene
both b and c
none of the above
Page 13
40.
The two most abundant isotopes of boron are 10B and 11B, with 11B being about 4
times more abundant. In the mass spectrum of trimethylborate [(CH3O)3B],
____________________________________.
A.
B.
C.
D.
41.
Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the
presence of a strong base to give 2-pentene as the only alkene product?
A.
C.
E.
42.
the peaks at m/z 103 and m/z 104 have equivalent intensities
the peak at m/z 103 has an intensity which is 4 times that of the
m/z 104 peak
the peak at m/z 103 has an intensity which is 1/4 the intensity of
the peak at m/z 104
none of the above
1-chloropentane
3-chloropentane
1-chloro-3-methylbutane
B.
D.
2-chloropentane
1-chloro-2-methylbutane
When (R)-2-butanol is treated with TsCl in pyridine, the product formed is:
A.
B.
C.
D.
E.
an achial compound.
a mixture of diastereomers.
a racemic mixture.
a single enantiomer.
none of the above.
Page 14
43.
What is the approximate chemical shift of an alkynyl carbon in 13C NMR
spectroscopy?
A.
44.
B.
30 ppm
C.
70 ppm
D.
120 ppm
E.
200 ppm
How many distinct p orbitals exist in the second electron shell, where n=2?
A.
45.
10 ppm
0
B.
1
C.
2
D.
3
E.
4
Which of the following additions to alkenes occur(s) specifically in a syn
fashion?
A.
B.
dihydroxylation using OsO4, H2O2
addition of H2
C.
D.
E.
F.
G.
hydroboration
addition of Hcl
both a and b
a, b, and c
none of the above
Page 15
46.
In the boat conformation of cyclohexane, the "flagpole" are located:
A.
B.
C.
D.
E.
47.
on the same carbon.
on adjacent carbons.
on C-1 and C-3.
on C-1 and C-4.
none of the above
Methylamine reacts with acetophenone to yield the:
A.
B.
C.
D.
E.
48.
iminium salt.
imine.
acetal.
amide
enamine.
The protons marked Ha and Hb in the molecule below are _____________.
Hb
Ha
CH3CH2
OH
A.
B.
C.
D.
E.
chemically equivalent
enantitopic
diastereotopic
endotopic
none of the above
Page 16
49.
Which of the following amines can be resolved into enantiomers?
A.
B.
C.
D.
E.
50.
Which of the following best describes DDT?
A.
B.
C.
D.
E.
51.
trimethylamine
3-pentanamine
2-pentanamine
dimethylammonium chloride
4-(dimethylamino)pyridine
a
a
a
a
a
chlorocarbon used to decaffeinate coffee beans
polybrominated organic compound used as a herbicide
Freon used as a foaming agent
mixed alkyl halide used as an anesthetic
polychlorinated organic compound used as an insecticide
In nucleophilic acyl substitution,:
A.
B.
C.
D.
E.
protonation of the the carbonyl is followed immediately by loss of
the leaving group.
loss of the leaving group is followed by rearrangement of the
carbocation.
addition to the carbonyl by a nucleophile is followed by loss of the
leaving group.
ester hydrolysis is followed by deprotonation.
an SN2 reaction occurs.
Page 17
52.
An ether solution of PhCO2H (A), PhNH2 (B), and PhCH3 (C) is extracted with
aqueous NaOH. The ether layer will contain what compound(s) after the
extraction?
A.
B.
C.
D.
E.
53.
+ B
+ C
+ C
+ B + C
only
The reaction of PhMgBr with CH3COCH2CH3 gives:
A.
B.
C.
D.
54.
A
A
B
A
A
an achiral product
a mixture of diastereomers.
the racemate of a chiral product.
a single enantiomer.
The nitration of anisole:
A.
B.
C.
D.
E.
proceeds more rapidly than the nitration of benzene and yields
predominantly the meta product.
proceeds more rapidly than the nitration of benzene and yields
predominantly the ortho, para products.
proceeds more slowly than the nitration of benzene and yields
predominantly the meta product.
proceeds more slowly than the nitration of benzene and yields
predominantly the ortho, para products.
proceeds at the same rate as the nitration of benzene and yields
predominantly the meta product.
Page 18
55.
The relationship between ketones and their corresponding enols is one of:
A.
B.
C.
D.
E.
56.
isomers.
stereoisomers.
enantiomers.
diastereomers.
tautomers.
Which of the following could result from the dehydration of an aldol?
A.
B.
C.
D.
E.
57.
4-methyl-3-penten-2-one
4-methyl-4-penten-2-one
4-methyl-5-hexen-2-one
4-methyl-4-hexen-2-one
3-methyl-4-penten-2-one
Which of the following best describes the geometry about the carbon-carbon
double bond in the alkene below?
CH3
CH 3
C
C
H
A.
Br
E
B.
Z
C.
Page 19
neither E nor Z
58.
Which of the following molecules is chiral?
A.
B.
C.
D.
E.
59.
Which of the following compounds has the most signals in the noise-decoupled 13C
NMR spectrum?
A.
B.
C.
D.
E.
60.
2,3-pentadiene
1,2-pentadiene
2-methyl-2,3-pentadiene
2-chloro-4-methyl-2,3-pentadiene
none of the above molecules is chiral
o-dibromobenzene
m-dibromobenzene
p-dibromobenzene
1,3,5-tribromobenzene
1,2,3,4-tetrabromobenzene
In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a:
A.
B.
C.
D.
E.
1,2-fashion.
1,3-fashion.
1,4-fashion.
1,5-fashion.
Diels-Alder reaction.
Page 20
61.
If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen
atoms must it also contain?
A.
n
B.
n+2
n-2
C.
D.
E.
F.
62.
2n+2
2n-2
Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?
A.
B.
C.
D.
E.
63.
2n
sodium
sodium
sodium
sodium
both a
(R)-2-butoxide
+
iodoethane
(S)-2-butoxide
+
iodoethane
ethoxide
+
(R)-2-iodobutane
ethoxide
+
(S)-2-iodobutane
and d would work equally well
Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds
via which of the following mechanistic pathways?
A.
SN1
B.
SN2
C.
D.
E.
E1
E2
none of the above
Page 21
64.
65.
Which of the following is not a possible termination step in the free radical
chlorination of methane?
A.
·CH3
+
Cl2
------->
CH3Cl
+
B.
·CH3
+
Cl·
------->
CH3Cl
C.
·CH3
+
·CH3
------->
CH3CH3
D.
·CH3
+
wall
------->
CH3-wall
E.
Cl·
+
wall
------->
Cl-wall
Cl·
Which of the following best describes the geometry about the carbon-carbon
double bond in the alkene below?
OCH 3
OH
Br
A.
B.
C.
66.
E
Z
neither E nor Z
Which of the following species is the least nucleophilic?
A.
(CH3)3CO-
B.
H2O
C.
(CH3)3N
D.
BF3
E.
CN-
Page 22
67.
What type of orbital do the lone pair electrons on oxygen occupy in ethanol?
A.
68.
C.
p
D.
sp
E.
sp2
F.
sp3
Which of the halogens below undergoes free radical halogenation with ethane most
rapidly?
A.
69.
B.
fluorine
B.
chlorine
C.
iodine
D.
bromine
E.
pyridine
In electrophilic aromatic substitution reactions the hydroxyl group is an
o,p-director because:
A.
B.
C.
D.
E.
it donates electron density to the ring by induction and
destabilizes the meta sigma complex.
it donates electron density to the ring by resonance and stabilizes
the ortho, para sigma complex.
it donates electron density to the ring by induction and stabilizes
the ortho, para sigma complex.
it donates electron density to the ring by resonance and
destabilizes the meta sigma complex.
it withdraws electron density from the ring by induction and
destabilizes the meta sigma complex.
Page 23
70.
How many nodes, other than the node coincident with the molecular plane, are
found in the highest energy π MO of 1,3-butadiene?
A.
B.
C.
D.
E.
71.
Which of the following is not a fused-ring heterocycle?
A.
B.
C.
D.
E.
72.
0
1
2
3
none of the above
purine
pyrimidine
benzofuran
indole
quinoline
Which of the following is a secondary amine?
A.
B.
C.
D.
E.
cyclohexylamine
3-pentanamine
methylamine
N,N-dimethylaniline
N-ethyl-1-propanamine
Page 24
73.
Which of the following statements is/are true?
A.
B.
C.
D.
E.
74.
hydrolysis.
DIBAH reacts with acid chlorides to yield primary alcohols after
hydrolysis.
Both a and b.
Both b and c.
What descriptive term is applied to the type of diene represented by
1,5-octadiene?
A.
B.
C.
D.
E.
75.
Two equivalents of Grignard reagent react with acid chlorides to
yield tertiary alcohols after hydrolysis.
LiAlH4 reacts with acid chlorides to yield secondary alcohols after
conjugated diene
cumulated diene
isolated diene
alkynyl diene
none of the above
The chemical shifts for protons α to a carbonyl group:
A.
B.
C.
D.
E.
are similar for all acid derivatives.
are farthest downfield for carboxylic acids.
are farther downfield than those α to a nitrile.
fall between δ 3.1 and δ 4.2.
fall between δ 1.3 and δ 1.8.
Page 25
76.
The strongest dichlorobutanoic acid is:
A.
B.
C.
D.
E.
77.
acid
acid
acid
acid
acid
Which of the functional groups below contain a hydroxyl group as a part of their
structure?
A.
B.
C.
D.
E.
F.
G.
78.
2,2-dichlorobutanoic
2,3-dichlorobutanoic
3,3-dichlorobutanoic
3,4-dichlorobutanoic
4,4-dichlorobutanoic
aldehyde
alcohol
carboxylic acid
amine
a, b, and c only
b and c only
all of the above
In the carbon NMR, in what region of the spectrum does one typically observe
carbons which are part of the aromatic ring?
A.
B.
C.
D.
E.
-10.0-0.0 ppm
40.0-60.0 ppm
80.0-100.0 ppm
120.0-150.0 ppm
200.0-220.0 ppm
Page 26
79.
Choose the correct hybridization for the atom indicated in the molecule below.
CH3CH2CH2CH3
A.
sp
B.
sp2
sp3
C.
D.
80.
none of the above
Which compound would show a larger than usual M+2 peak?
A.
CH3CH2CN
B.
CH3CH2SCH3
C.
Page 27
CH3CH2CO2H
D.
CH3(CH2)2CH3
Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1
Chapter/
Question
11-54
7-62
8-50
6-1
20-50
2-26
10-1
4-41
22-60
6-13
21-52
1-16
13-32
9-14
22-32
4-45
19-45
22-23
20-30
11-49
11-19
6-33
7-57
16-6
14-14
7-32
18-32
4-16
21-18
20-49
16-53
18-14
22-12
1-26
8-62
20-38
6-49
11-43
2-53
11-50
7-53
10-26
14-18
1-5
8-60
3-54
22-20
12-13
19-12
6-12
21-9
(-,b,-)
(-,e,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,c,-)
(-,a,-)
(-,a,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,a,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,c,-)
(-,b,-)
(-,a,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,a,-)
(-,e,-)
(-,a,-)
(-,c,-)
(-,b,-)
(-,b,-)
(-,b,-)
Test
Question
1
2
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18
19
20
21
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37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
Correct
Answer
E
B
C
B
D
B
A
A
B
D
C
E
B
C
E
B
B
B
A
A
C
B
C
C
A
B
A
B
E
D
E
A
E
C
B
B
E
B
E
C
C
D
C
D
F
D
B
B
C
E
C
Page 1
Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1
Chapter/
Question
20-53
10-46
17-10
22-4
22-25
7-20
15-6
16-52
22-44
3-3
13-20
7-54
4-7
7-56
6-20
9-4
4-43
17-8
15-13
16-60
19-11
21-27
15-8
21-7
20-47
2-59
16-50
2-20
11-17
(-,a,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,e,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,b,-)
(-,a,-)
(-,b,-)
(-,a,-)
(-,a,-)
Test
Question
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
Correct
Answer
C
C
B
E
A
A
A
B
C
E
A
D
A
A
D
F
A
B
D
B
E
A
C
A
A
F
D
C
B
Page 2
Statistics for Test “TestFinal-360-1996-PracMicroo”. Total questions: 80
Key Word Total
Difficulty Level Total
Question Type Total
None
None
a) Easy
b) Mod
c) Diff
d)
e) Mod
f) Diff
Free format
True or False
Multiple choice
Matching
80
2
28
44
3
0
3
0
0
0
80
0