Practice Final Exam, Chemistry 2210, Organic Chem I
1. What is the hybridization of the indicated atom in the following molecule?
A. sp3
B. sp2
C. sp
D. not hybridized
2. Name the functional groups in the following molecule (in order from left to right).
O
NH
HO
A.
B.
C.
D.
O
O
Secondary alcohol, ketone, secondary amine, ether
Primary alcohol, ketone, secondary amine, ester
Secondary alcohol, amide, ketone, ether
Primary alcohol, amide, ester
3. Which of the following is the strongest acid?
OH
B.
A.
O
NH2
C.
D.
OH
4. Give the IUPAC name of:
OH
A. trans-1-neopentyl-2-cyclohexanol
C. trans-2-tert-butylcyclohexanol
B. cis-2-tert-butylcyclohexanol
D. cis-2-sec-butylcyclohexanol
5. Give the IUPAC name of:
Cl
H3C
H
Cl
Cl
HO
CH3
H
A.
B.
C.
D.
(2R,3R,4S)-3,3,4-trichloro-2-pentanol
(1R,3S)-2,2,3-trichloro1,4-dimethyl-1-butanol
(2R,4R)-3,3,4-trichloro-2-pentanol
(2R,4S)-3,3,4-trichloro-2-pentanol
6. Which of the following is true about this reaction?
O
Cl
Br
A.
B.
C.
D.
The product will have R configuration.
A racemic mixture is produced.
The product will have S configuration.
The product is not optically active.
DMSO
7. What is the IUPAC name of this compound?
A. cis-2,3-dimethyl-3-hexene
C. (Z)-2,3-dimethyl-3-hexene
B. trans-2,3-dimethyl-3-hexene
D. (E)-2,3-dimethyl-3-hexene
8. What will be the major organic product of the following reaction?
KOH
heat
Br
A.
B.
D.
C.
OH
9. What is the major product of the following reaction?
10. Which of the following compounds would produce both of these ketones in an ozonolysis
reaction?
O
O
and
O
A.
C.
B.
D.
11. Which of the following is the least stable radical?
12. Which of the following reactions would form 1-bromo-3-methyl butane from 3-methyl-1butene?
A. Reaction with HBr
B. Reaction with HBr in presence of peroxides
C. Reaction with NBS in presence of light
D. Reaction with Br2 in presence of light
13. Arrange these hydrogens by aciditity, most acidic first.
O
b
H O
O H
c
d
H O CH2
H
a
A. c > d > b > a
B. a > c >d > b
C. c > b > d > a
D. a > c > b > d
14. Which structure has the IUPAC name: 7-tert-butylbicyclo[4.3.1]decane.
A.
B.
C.
D.
15. Which conformer has torsional strain and steric strain?
H
CH3
H
A.
CH3
H
CH3
H
H
B.
H H
CH3
CH3
CH3
H
C.
H H
H
H
H
CH3
H
D.
H
H
CH3
16. Which description is correct for the following compound?
A. Achiral
C. Optical active
B. Meso
D. It is not superimposable on its mirror image
17. Which one is the best synthetic route to obtain the following compound?
A.
B.
C.
D.
18. What is the product of the following reaction?
Br
NaOCH3
HOCH3
A.
B.
and
C.
D.
and
19. Which one is the correct set of reagents/conditions to carry out the following reaction?
OH
A. Hg(OAc)2, H2O, then NaBH4
B. BH3▪THF, then H2O2/OHC. H3O+, H2O, heat
D. Cold KMnO4, H2O, HO-
20. Which would be the best way to carry out the following synthesis?
A.
B.
C.
D.
(1) Br2/heat; (2) (CH3)3COK/(CH3)3COH; (3) cold KMnO4, H2O, HO(1) Br2/heat; (2) KOH/CH3OH; (3) cold KMnO4, H2O, HO(1) Br2/CCl4; (2) (CH3)3COK/(CH3)3COH; (3) C6H5COOOH; H3O+
(1) Br2/CCl4 (2) KOH/CH3OH /(CH3)3COH; (3) C6H5COOOH; H3O+
21. In the molecule shown below, please arrange by bond dissociation energy, largest BDE first.
A. a > c > b > d
B. a > c > d > b
C. c > a > d > b
22. Which is the major product?
A.
B.
C.
D.
D. c > a > b > d
23. Which is the major product?
A.
B.
C.
D.
24. Which reagent(s) are most suitable to accomplish the following reaction:
A.
B.
C.
D.
NH3 then ethyl bromide
Ethyl bromide then NH3
NaNH2 then ethyl bromide
Ethyl bromide then NaNH2
25. Which base/ conjugate acid pair is correct
26. Which carbocation is likely to undergo a 1,2 hydride shift?
27. Name the following compound (IUPAC rules):
A. (S,E)-hex-2-en-4-ol
C. (R,Z)-hex-2-en-4-ol
B. (R,E)-hex-4-en-2-ol
D. (S,E)-hex-4-en-2-ol
28. Which of the following reactions would most likely occur via an SN1 pathway?
29. For the CO2 molecule, what is the shape, bond angle, and hybridization of the carbon atom?
A.
B.
C.
D.
Bent, 109°, sp2
Bent, 120°, sp3
Linear, 180°, sp
Pyramidal, 120°, sp4
30. Which reaction favors formation of the products?
31. The compound which best fits the IR spectrum below is:
A. C6H5NH2
B. CH3CH2OH
C. CH3CO2CH2CH3
D. CH3CO2H
32. First, identify the compound with the highest boiling point. What is its Index of Hydrogen
Deficiency?
O
O
O
OH
A. 0
B. 0.5
C. 1
D. 2
33. How many tetrahedral stereocenters (asymmetric carbons; chirality centers) does the
following molecule have?
HO
A. 3
B. 2
C. 1
D. 0
34. Consider the following reaction and kinetic data and deduce the mechanism of the reaction
from this information:
A. SN1
[RBr]
[NaOH]
relative rate
0.06
0.03
0.06
0.02
0.02
0.01
6
3
3
B. SN2
C. E1
D. E2
35. The alkene that forms in the following alcohol dehydration reaction as the major product is:
A. tetrasubstituted B. trisubstituted C. disubstituted D. monosubstituted
36. Which of the following is the best synthesis for 2,2-dibromopentane?
A.
B.
C.
D.
Addition of Br2 in CCl4 to 1-pentene.
Bromination of pentane using excess of Br2 in the presence of light.
Addition of HBr to 1-pentyne in the presence of peroxides.
Addition of HBr to 1-pentyne.
37. How many bonds in this molecule are formed by an s-sp3 overlap?
O
H 2N
A. 4
OH
B. 5
C. 6
D. 7
38. Rank the following bases in order of increasing base strength (weakest base first)
A. II<III<I<IV
C. II<I<III<IV
B. II<III<IV<I
D. II<I<IV<III
39. What are the products of the reaction shown below?
CH3C≡CNa + CH3OH → ?
A. H3COC CH
+
NaCH3
B. CH3C CCH3
+
NaOH
C.
D. CH3C COCH3
+
NaOH
40. When the following 4 alkenes are combusted, which would give off the least heat?
A.
(CH3)2C=CHCH2CH3
B.
CH3CH=CHCH(CH3)2
C.
(CH3)2C=C(CH3)2
D.
CH2=C(CH3)CH2CH2CH3
41. 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, HOD. HBr; than NaNH2; then H2/Pt
42. What is the major product?
1) Hg(OAC)2, THF, H2O
2) NaBH4, OHOH
OH
OH
OH
A
C
B
D
43. The free radical chlorination of 2,2-dimethylbutane produces this number of
monochlorinated products, including stereoisomers
A. 2
B. 3
C. 4
D. 5
44. Which of the following is a propagation step in the chlorination of methane?
A.
B.
C.
D.
Cl-Cl  2 Cl·
Cl· + CH4  CH3· + HCl
CH3· + H3CCl  CH4 + ·CH2Cl
CH3· + CH3·  CH3CH3
45. Determine formal charges of boron and oxygen in the following structure. Lone pairs are not
shown, so use the octet rule to determine where they are:
H
H
F
F
B
F
C
O
H
H
C
H
H
A. B = +1; O = + 1
C. B = +1; O = - 1
B. B = -1; O = - 1
D. B = -1; O = + 1
46. What is wrong with the mechanistic arrow shown here?
A. It should start on the alkyne carbon.
B. It should start on a hydrogen attached to the nitrogen.
C. It should start on an unshared pair on nitrogen, end at the H on the alkyne, and a second
arrow should start at the bond between the C and H on the alkyne and end on the terminal carbon
of the alkyne.
D. There should be two arrows-one from nitrogen and from the alkyne carbon.
47. What is the IUPAC name for the following compound?
CH3
H
H
H
Cl
A. (R)-6-chloroheptane
B. (S)-3-chloroheptane
C. (R)-1-chloro-2-methylhexane
D. (S)-6-chloro-5-methylhexane
48. Pure (S)-bromobutane has a specific rotation of +100.0o. If you have a mixture of R and S
enantiomers and this mixture rotates light by -6.0, then what is the composition of your mixture.
(What is the percent of R and what is the percent of S in the mixture?)
A. 60% R and 40% S
B. 40% R and 60% S
C. 47% S and 53% R
D. 47%R and 53% S
49. Which of the following compounds is the same as compound I?
I
II
III
IV
A. II
B. III
C. IV
D. III and IV
50. Rank the following substrates from most to least reactive in an SN2 reaction.
I.
II.
III.
IV.
A. I>II>III>IV
C. II>III>I>IV
B. IV>I>II>III
D. III>II>I>IV