Practice Final Exam, Chemistry 2210, Organic Chemistry 1
1. Which of the following molecules exhibits a net dipole moment greater than zero?
A. BF3
B. NH3
C. SO3
D. CCl4
2. The most stable chair conformation of cis-2-tert-butylcyclohexanol is:
A. with axial OH and equatorial tert-butyl groups
B. with equatorial OH and axial tert-butyl groups
C. with equatorial OH and equatorial tert-butyl groups
D. with axial OH and axial tert-butyl groups
3. The following molecules are:
COOH
COOH
HO
H
H
Br
H
H3C
CH3
A. enantiomers
4.
OH
Br
H
B. diastereomers
C. same compound
D. constitutional isomers
Give the IUPAC name of the following molecule:
H
OH
CH3
H
A. trans-1-methyl-2-cyclohexanol
C. trans-2-methylcyclohexanol
B. cis-1-methyl-2-cyclohexanol
D. cis-2-methylcyclohexanol
5. What species acts as the base in the following reaction:
A.
B.
C.
D.
Propyne
Na+
NH2NH3
6. Which of the following will give the product shown as the major product?
Br
?
Br2
A.
Br2
C.
7.
KOH
Light
HBr
peroxides
D.
Br2
KOH
B.
Light
Light
Br2
KOH
HBr
Light
Which of the following is a meso compound?
CH 3
HO
H
OH
Br
C
H
H
Br
C
H
CH 3
A.
I only
I
II only
B.
II
Both I and II
C.
D.
Neither I nor II
8. Which one is the intermediate of the following reaction?
H 3C
C
H 3C
CH2 + HBr
ROOR
H3C
H3C
H 3C
C
H3C
A.
CH3
C
H3C
B.
CH2
H3C
C
H3C
CH3
C
CH2Br
H3C
C.
D.
9. What is the major product of the following reaction?
10. What is the major product?
1) Hg(OAC)2, THF, H2O
2) NaBH4, OHOH
OH
OH
OH
A
B
C
D
11. Which of the following is NOT a stereospecific reaction?
A.
B.
C.
D.
Addition of bromine to cyclohexene in CCl4
Acid catalyzed hydrolysis of epoxides
Hydrogenation of 2-butyne with H2/Ni2B
Chlorination of propane in the presence of light
12.
What is (are) the major organic product(s) of the following reaction?
CH 3
+
CH 3CH 2O
?
CH 3CH 2CH Br
CH 3
A.
C.
CH 3CH 2-O-CHCH 2CH 3
CH 3CH 2-O-C(CH 3)3
B.
CH 3CH 2-OH +
D.
CH 3CH 2-OH
+
CH 3CH
CHCH 3
CH 3CH 2CH
CH 2
13. What is the strongest intermolecular force present in a pure sample of 2-bromobutane?
A.
B.
C.
D.
van der Waals
Dipole-Dipole
Hydrogen Bonding
Ion-Ion
14. Which of these is not used to make an alcohol into a substrate with a good leaving group?
A.
SOCl2
B.
HBr
C.
NaH, then CH3SO2Cl
D.
NaCl
15.
What is the IUPAC name of the following molecule?
A. 5-chloro-3-hexanol
C. 3-chloro-1-ethyl-1-butanol
B. 2-chloro-4-hexanol
D. 3-chloro-1-ethyl-3-methyl-1-propanol
16.
Identify the major product of the following reaction?
OH
H3 PO4
heat
A.
B.
C.
D.
17. In the absence of specific data, it can only be said that (R)-2-bromopentane is:
A. Dextrorotary (+)
B. Levorotary (-)
C. optically inactive
D. optically active
18. Which of the following is a propagation step in the chlorination of methane?
A. Cl-Cl  2 Cl·
B. Cl· + CH4  CH3· + HCl
C. CH3· + Cl·  CH3Cl
D. CH3· + CH3·  CH3CH3
19. What will be the major product of the following reaction?
20. What is the hybridization of the indicated atom in the following species?
A. sp3
B. sp2
C. sp
D. not hybridized
21.
Which of the following reaction sequences gives the compound shown below as the
major organic product?
CH 3
CH 3-C-C
C-CH 2CH 3
CH 3
CH 3
A.
CH 3-C-C
CH
KOH
CH 3
CH 3CH 2-Br
CH 3
CH 3-C
B.
CH 3CH 2-C
CH
CH 3
C.
CH 3-C-C
?
CH
NaNH 2
NaNH 2
Br
CH 3
?
CH 3CH 2-Br
?
CH 3
More
than one 2of+the
D. (CH
H2,above.
Pt
3)3CCH=CH
?
22. Consider the following reaction and the major mechanism that takes place. Which of the
following changes would not increase the rate of substitution?
A.
B.
C.
D.
Using NaNH2 instead of NaOH
Using 1-iodopropane instead of 1-chloropropane
Using DMSO instead of CH3OH
Using 2-chloropropane instead of 1-chloropropane
23. What would you combine with 1-butene to produce 2-bromobutane?
A.
Br2 with heat
B.
PBr3
C.
HBr without peroxide
D.
Br2 in the cold and dark
24.
Which of the following correctly describes the carbon-carbon triple bond in acetylene,
HC≡CH?
A.
There is one sigma (σ) bond formed by overlap of sp hybrid orbitals and two pi (π) bonds
formed by overlap of p orbitals.
There is one sigma (σ) bond formed by overlap of sp2 hybrid orbitals and two pi (π)
bonds formed by overlap of p orbitals.
There is one sigma (σ) bond formed by overlap of sp3 hybrid orbitals and two pi (π)
bonds formed by overlap of p orbitals.
There are three pi (π) bonds formed by overlap of p orbitals.
B.
C.
D.
25. What is the product of the following reaction?
26. What is the major product of the following reaction?
Cl2
H2 O
Cl
Cl
B.
A.
Cl
Cl
Cl
Cl
C.
D.
OH
OH
27. List the following conformations of 2,3-dibromobutane in the order of increasing their
stability (least stable first):
Br
CH3
Br
H3C
H3C
H
H3C
H
H
Br
Br
H
CH3 H
Br
H3C CH3
I
II
III
A. I<II<III<IV
28.
H
B. I<III<IV<II
C. III<I<II<IV
Br
H
CH3
H
Br
Br
IV
D. III<I<IV<II
Which of the following would be soluble in cold concentrated sulfuric acid, decolorize
bromine in carbon tetrachloride, and have an index of hydrogen deficiency of 2?
A.
CH 3 CH CH CH 3
B.
CH 3 CH CH 2
C.
CH 3 CH 2 C CH
D.
CH 3 CH 2 CH 2 CH 3
29.
Consider the reaction below. What is the mechanism of the reaction based on the data
given in the table below?
+
CH 3CH 2O
+ CH 3CH 2OH
Br
Experiment
1
2
3
A.
Sn1
B.
[C 6H11Br]
[C 2H5O ]
0.02
0.08
0.06
Sn2
Relative Rate
0.02
0.02
0.06
C.
E1
1
4
93
D.
E2
30. The free radical chlorination of 2,2-dimethylbutane produces this number of chlorinated
products, including stereoisomers
A. 2
B. 3
C. 4
D. 5
31. Which of the following is NOT a valid resonance structure of the others?
32. Which of the following compounds releases the most energy upon combustion?
33.
What is the name of the following compound?
A.
C.
6,6-diethylbicyclo[3.2.2]nonane
2,2-diethylbicyclo[3.2.2]nonane
B.
D.
1,1-diethylbicyclo[3.2.2]nonane
5,5-diethylbicyclo[3.2.2]nonane
34. What is the major product of the following reaction?
35.
omit
36. Which reaction sequence would convert cis-2-butene to trans-2-butene?
A. Br2/CCl4; then 2 NaNH2; then H2/Ni2B
B. Br2/CCl4; then 2 NaNH2; then Li/NH3
C. H3O+, heat; then cold dilute KMnO4
D. HBr; than NaNH2; then H2/Pt
37.
What is the correct IUPAC name of the following compound?
CH 2CH 3
CH 3CH 2CH 2
CH 3
CH 2CH(CH 3)2
Br
H
A.
B.
C.
D.
3-bromo-3-ethyl-5-methyl-2-propylhexane
3-bromo-3-isobutyl-4-methylheptane
4-bromo-4-ethyl-2,5-dimethyloctane
5-bromo-5-ethyl-4,7-dimethyloctane
38. Which of the following protons is the most acidic?
B.
A.
D.
OH
H
HOOC
C
C-H
C.
39. Which of the following best represents the mechanism for E2 reaction between ethyl
bromide and ethoxide ion?
-
H H
Br
C
C
H
HH
A.
C2H5O
H H
Br
C
C
H
HH
B.
-
C2H5O
H H
Br
C
C
H
HH
C.
H H
H
C
C
H
H Br
D.
-
-
C2H5O
C2H5O
40. How many sigma bonds are present in the following molecule?
A. 4
41.
B. 12
C. 14
D. 15
Which of the following IS a product of the reaction shown?
CH 3
H
H
F
H
+
Cl2
light
?
CH3
F
H
A.
CH 3
Cl
H
B.
CH3
C.
F
H
CH 2Cl
H
H
CH 3
F
H
CH 3
H
Cl
CH 3
D.
CH3
More
thanHone of these
F
H
H
CH2Cl
42.
Which set of reagents would cause the following conversion?
D
D
CH 3
?
OH
H
CH 3
A.
BH 3:THF, then H 2O2/OH
B.
H2O/Hg(OAc)2THF, then NaBH 4/OH
C.
H3O , H 2O, heat
D.
More
H
heatone of these
2SO4,than
43. Which of these is the best way to synthesize methyl tert-butyl ether?
A. CH3OH + (CH3)3COH with H+, heat
B. CH3Cl + (CH3)3CONa
C. CH3OH + (CH3)3CONa
D. CH3ONa + (CH3)3CCl
44. Which of the following molecules can most easily be distinguished from the others using IR
spectroscopy?
45. Which of the following is the best synthesis for 1,1-dibromopropane?
A.
B.
C.
D.
Addition of Br2 in CCl4 to propene.
Bromination of propane using Br2/light.
Addition of HBr to propyne.
Addition of HBr to propyne in the presence of peroxides.
46. Which of the following reactions would not occur?
_
A. CH 3 + C6 H5 NH2
B. CH CH _ + CH OH
3
2
3
C. OH
_
D. OH
47.
+ CH4
_
+ CH3 COOH
Which of the following free radicals is the LEAST stable?
CH 2CH 3
A
B.
CH 2
CH 3
CH
C.
D.
CH 2CH 2
CH 3
48. Which of the following is the least soluble in water?
A. CH3CH2OH
B. CH3COOH
C. CH3COCH3
D. CH3CH2OCH3
49. Which of the following is the most likely product for the following reaction:
H
H
CNa
H3CC
OH
ONa
B.
A.
C.
50.
H
C
H3CC
C
H
D. Mixture of about equal
CCH3
amounts of products B and C
What reaction would you expect to have the smallest energy of activation?
o
 H (KJ/mol )
A.
CH 3
+
CH 3
CH 3CH 3
B.
CH 4
+
F
CH 3
+
HF
-134
C.
CH 4
+
I
CH 3
+
HI
+138
D.
CH 4
+
Br
CH 3
+
HBr
+69
-368