PRACTICE FINAL EXAMINATION
1.
Which of the following compounds is a primary alcohol?
CH2 OH
HO
A.
2.
ORGANIC CHEMISTRY 2210
CH3
B.
OH
C.
D.
O
What is the name of the compound shown?
H
OH
H
Cl
A.
B.
C.
D.
3.
Which of the following statements about ethanol, CH3 CH2 OH, is true?
A.
B.
C.
D.
4.
trans-4-chlorocyclohexanol
cis-4-chlorocyclohexanol
trans-1-chloro-4-cyclohexanol
cis-1-chloro-4-cyclohexanol
It contains one π bond.
It contains six σ bonds.
The C-O-H bond angle is approximately 120˚.
The H-C-H bond angles are approximately 109.5˚.
Which of the alkenes shown has the greatest heat of combustion?
A. CH2 =CHCH 2 CH2 CH3
B. (CH3 )2 C=CHCH 3
C. CH3 H
\
/
C=C
/
\
H
CH 2 CH3
D. CH 3 CH2 CH3
\
/
C=C
/
\
H
H
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5.
Which of the compounds shown is isobutyl chloride?
A.
B.
C.
D.
6.
What is the name of the compound shown?
A.
B.
C.
D.
7.
CH3 CH2 CH(CH 3 )2
\
/
C=C
/
\
H
CH 3
E
Z
cis
trans
What is the most important reason for the fact that cyclohexane is the most stable of the
cycloalkanes of twelve carbons or less?
A.
B.
C.
D.
9.
Bicyclo[4.1.0]heptane
Bicyclo[3.1.1]heptane
Bicyclo[3.2.0]heptane
Bicyclo[5.4.0]heptane
Which of the following designations describes the compound at right?
A.
B.
C.
D.
8.
(CH3 )3 CCl
CH3 CHClCH2 CH3
(CH3 )2 CHCH 2 Cl
CH 3 CH2 CH2 CH2 Cl
There is eclipsing along two of the carbon-carbon bonds in the boat conformation.
There is eclipsing along four of the carbon-carbon bonds in the chair conformation.
Both torsional and bond angle strain are minimized in the chair conformation.
Both torsional and bond angle strain are minimized in the boat conformation.
What is the relationship between the compounds shown?
H
H
Cl
Cl
Cl
Cl
H
H
A. Same compound
10.
B. Enantiomers
C. Diastereomers
Which of the following nucleophiles is the most reactive?
A. CH3 COOH
B. CH3 COO –
C. CH3 OH
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D. CH3 O–
D. Structural isomers
11.
Which of these is the best method for preparing 1-bromopropane, CH3 CH2 CH2 Br?
CCl4
A. CH3 CH2 CH3 + Br2 ------->
light
B. CH3 CH2 CH3 + Br2 -------->
peroxides
C. CH3 CH=CH 2 + HBr -------------->
no peroxides
D. CH 3 CH=CH 2 + HBr ------------------>
12.
What is the relationship between the compounds shown?
CH3 CH2
CH3 CH2
Cl
H
C
|
CH3
A. Same compound
13.
B. Enantiomers
C. Diastereomers
D. Structural isomers
What is the name of the compound shown?
H
OH
H
H
A.
B.
C.
D.
14.
CH3
Cl
C
|
H
CH2 CH3
CH(CH 3 )2
4-heptanol
2-methyl-3-hexanol
1-isopropyl-1-butanol
1-isopropyl-2-ethylethanol
Two structures are both superimposable on each other and the mirror images of one
another. What is the relationship between them?
A.
B.
C.
D.
Same compound
Enantiomers
Diastereomers
Structural isomers
129
15.
Which of the following reactions yields (CH3 )3 CCl?
A. (CH3 )3 COH + HCl --->
CCl4
B. (CH3 )2 C=CH 2 + Cl 2 ------>
C. (CH3 )2 CHCH 2 OH + SOCl2 --->
CCl4
D. (CH 3 )3 CH + Cl2 ------>
16.
Which of the following acid-base reactions occurs as shown?
A.
B.
C.
D.
17.
CH3 COONa + HC≡CH ---> CH3 COOH + HC≡CNa
CH3 ONa + HC≡CH ---> CH3 OH + HC≡CNa
NaOH + HC≡CH ---> H2 O + HC≡CNa
CH 3 NHNa + HC≡CH ---> CH3 NH 2 + HC≡CNa
What are the hybridizations of the carbon atoms numbered 1 and 2 in the structure shown?
1
2
A. sp2 , sp3
18.
B. sp2 , sp2
C. sp, sp3
D. sp, sp2
Which of the following is NOT a meso compound?
A.
H
H
B.
H
HO
H
H
C.
H
H
OH OH
OH OH
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D.
HO
OH
OH
H
19.
What are the major products of the reaction shown?
CCl4
CH3 + Br2 -------> ?
Br H3 C
Br
Br
H H3 C
H
Br
Br
H
CH3
Br
Br
CH3
IV
H
I
II
Br
III
A. I and III B. I and IV C. II and III D. II and IV
20.
What is/are the major organic product(s) of the reaction shown?
O
21.
Na
+ CH3 CH2 CH2 Br ---> ?
A.
OH + CH2 =CHCH 3
B.
+ CH3 CH2 CH2 OH
C.
OCH 2 CH2 CH3
D.
OCH(CH 3 )2
What is the configuration of the molecule shown?
CH3
CH2 CH3
C—C
H
Br
Br
H
A. 2S, 3S
B. 2S, 3R
C. 2R, 3S
D. 2R, 3R
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22.
What is the major organic product of the reaction shown?
BH3°THF H 2 O2 , OH–
(CH3 )2 C=CHCH 3 -------------> ---------------> ?
CH3
CH3
CH3
CH3
|
|
|
|
A. CH2 CHCH 2 CH3 B. CH3 CCH2 CH3 C. CH3 CHCHCH 3 D. CH 3 CHCH 2 CH2
|
|
|
|
OH
OH
OH
OH
23.
What is the relationship between the compounds shown?
CH3
CH2 CH3
H
H
CH3
OH
H
H
CH3
A. Same compound
24.
CH3
OH
CH2 CH3
B. Enantiomers
C. Diastereomers
D. Structural isomers
Which of the following solutions can be used in a test to distinguish between the
compounds CH2 =CHCH 2 CH3 and CH2 =CHCH 2 CH2 Br?
A. conc. H2 SO 4 B. Br2 /CCl4 C. AgNO3 /ethanol D. KMnO4 /H2 O
25.
What is the best explanation for the relative stabilities of the gauche and anti forms of
butane? The _____ form has more _____ strain.
A.
B.
C.
D.
26.
gauche . . . torsional
gauche . . . steric
anti . . . torsional
anti . . . steric
What are the predicted shape and bond angle of formaldehyde, H2 C=O?
A.
B.
C.
D.
Trigonal pyramid, 109.5˚
Trigonal planar, 109.5˚
Trigonal pyramid, 120˚
Trigonal planar, 120˚
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27.
28.
Which of the following sequences can be used to make
A.
H2 SO 4
CH2 I2
OH ----------> ----------->
heat
Zn(Cu)
B.
KOH
CH2 I2
OH ---------> ----------->
heat
Zn(Cu)
C.
H2 SO 4
CHCl3
Br ----------> ---------------->
heat
KOC(CH3 )3
D.
KOH
CHCl 3
Br ---------> ---------------->
heat
KOC(CH3 )3
?
An unknown alkene was subjected to ozonolysis, and the product of the reaction was the
compound shown. What is the structure of the unknown?
O
CH 3
O
||
|
||
CH3 CCH2 CHCH 2 CCH3
CH3
CH3
CH3
CH3 B.
A.
CH3
C.
CH3
D.
CH3
CH3
CH3
29.
Which of the arrows gives the direction of the dipole moment of the molecule shown?
Br Br
C
H
A.
H
B.
C.
D.
133
30.
Which of the following sequences gives cyclohexane from cyclohexanol?
A.
B.
C.
D.
31.
KOH, alcohol, heat; then Zn, HCl
Zn, HCl; then H2 , Pd
H2 , Ni; then H2 SO 4 , heat
H 2 SO 4 , heat; then H2 , Pt
Which of the following compounds is the least soluble in water?
A.
32.
OH
B.
OH
Cl
D.
Cl
What are the bases in the reaction shown?
OH + NH2 I
O- + NH3
II
A. I and III
33.
C.
III
B. I and IV
IV
C. II and III
D. II and IV
What is the value of ∆H in kJ mol-1 for the reaction below? Bond energies in kJ mol-1 are:
CH3 CH2 -OH, 383; CH3 CH2 O-H, 431; HO-H, 498; CH3 CH2 -OCH 2 CH3 , 335.
2 CH3 CH2 OH ---> H2 O + CH3 CH2 OCH 2 CH3
A. +29
34.
C. -67
D. -96
Which of the SN2 reactions below is the FASTEST?
A.
B.
C.
D.
35.
B. -19
CH3 Br + HC≡C– ---> CH3 C≡CH + Br–
CH3 Br + HC≡CH ---> CH3 C≡CH + HBr
CH3 CH2 Br + HC≡C– ---> CH3 CH2 C≡CH + Br–
CH 3 CH2 Br + HC≡CH ---> CH3 CH2 C≡CH + HBr
One of the two carbon-carbon bonding orbitals in ethylene, H2 C=CH 2 , is formed from the
overlap of ____ orbitals on the carbons, and the other is formed from the overlap of _____
orbitals.
A. sp, p B. sp2 , p
C. sp2 , sp D. p, p
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36.
Rate data for the reaction shown
is given in the table at right.
What is the mechanism of this
reaction?
Run
no.
[CH3 CH2 I]
[CH3 O– ]
Rel.
Rate
1
2
3
0.01
0.02
0.01
0.01
0.01
0.02
1
2
2
CH3 CH2 I + CH3 O– ---> CH3 CH2 OCH 3 + I–
A. SN1 B. SN2 C. E1 D. E2
37.
Which of the carbocations shown do NOT rearrange?
+
+
+
+
I. CH3 CH2 CH2 CH2 II. CH3 CHCH 2 CH3 III. (CH3 )2 CHCH 2 IV. (CH3 )3 C
A. I and III B. I and IV C. II and III D. II and IV
38.
Which of the following compounds has the highest boiling point?
A. CH3 CH2 ONa B. CH 3 CH2 OCH 3 C. CH3 CH2 CH2 CH3 D. CH 3 CH2 CH2 OH
39.
Which of the following is the best synthesis of cyclohexene from cyclohexane?
A.
B.
C.
D.
40.
KOH, alcohol
H2 SO 4 , heat
Br2 , light; then KOH, alcohol
Br2 , CCl4 ; then H2 SO 4 , heat
Which of the following is a sigma (σ) bonding orbital? Nuclei are indicated by solid dots,
and the signs of the wave functions are shown.
+
A.
-
+
B.
+
D.
C.
-
-
135
+
+