TKJ4100: Selvstendig prøve 1 / 2010
What is the IUPAC name of the following compound?
H
1.
H
3
C
CH
3
H
A) trans -1,4-dimethylcyclohexane
B) cis -1,4-dimethylcyclohexane
C) trans -1,3-dimethylcyclohexane
D) cis -1,3-dimethylcyclohexane
2. Which statement is correct concerning the relative stabilities of the two conformations, A and B, below:
CH
3
H
H
H
3
C H
CH
3
H CH
3
A B
A) A is more stable.
B) B is more stable.
C) A and B are equal in stabilities.
D) A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
3. How many isomeric alkenes of formula C
5
H
10
, including stereoisomers, are possible?
A) three
B) four
C) five
D) six
E) seven
Page 1

4. How many stereoisomers are there of D-fructose(including D-fructose), shown below.
CH
2
OH
O
HO
H
H
OH
H OH
A) four
CH
2
OH
B) six
C) eight
D) six
5. Propose a mechanism for the following reaction.
H
2
SO
4
O
HOCH
2
CH
2
CH
2
CH=CH
2
CH
3
6. Arrange the following carbocations in order of their decreasing stabilities (most stable first).
CH
3 CH
2
CH
3
A B C
A) A>B>C
B) C>B>A
C) A>C>B
D) B>C>A
Page 2

7. Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, NaOCH
2
CH
3
?
H
3
C CH
3
Br
H
3
C CH
3
H
3
C CH
3
Br
Br
A B C
A) A and B
B) A and C
C) B and C
D) A, B, and C
8. What is the estimated C-C-C bond angle in the following structure?
A) 90 o
B) 109.5
o
C) 120 o
D) 180 o
9. Identify the major organic product expected from the acid-catalyzed dehydration of
2-methyl-2-pentanol.
A) 2-methyl-1-pentene
B) 2-methyl-2-pentene
C) 3-methyl-1-pentene
D) cis -3-methyl-2-pentene
Page 3

10. Identify the nucleophile in the following electrophilic addition reaction.
CH
3

CH
3
)
2
C=CH
2
+ IN
3
CH
3
CCH
2
I
N
3
1) N
3
-
2) N
3
+
3) I
+
4) I
-
A) is 1
B) is 2
C) is 3
D) is 4
11. What is the rate limiting step in the following reaction?
(CH
3
)
3
CCl + H
2
O (CH
3
1) (CH
3
)
3
CCl (CH
3
)
3
C
)
3
COH + HCl
+
+ Cl
-
2) (CH
3
)
3
C
+
+ H
2
O (CH
3
)
3
C-OH
2
+
3) (CH
3
)
3
C-OH
2
+
+ H
2
O (CH
3
)
3
COH + H
3
O
+
4) H
3
O
+
+ Cl
-
HCl + H
2
O
A) is 1
B) is 2
C) is 3
D) is 4
12. What is the estimated dihedral angle between the two methyl groups on the structure shown below?
A) 30 o
B) 60 o
C) 90 o
D) 120 o
Page 4

13. The rate law for the following reaction is:
DMSO
CH
3
CH
2
CH
2
Cl + NaCN
A) rate = k[CH
3
CH
2
CH
2
Cl]
B) rate = k[CH
3
CH
2
CH
2
Cl][NaCN]
C) rate = k[CH
3
CH
2
CH
2
Cl][NaCN]
2
D) rate = k[CH
3
CH
2
CH
2
Cl]
2
[NaCN]
14. How many isomeric alkenes are possible, including stereoisomers, in the following reaction?
Br NaOCH
2
CH
3
CH
3
CH
2
OH
A) one
B) two
C) three
D) four
E) five
15. What is(are) the major product(s) of the following reaction?
1) B
2
H
6
, diglyme
2) H
2
O
2
, NaOH
OH
2) 4) both 2 and 3
OH
A) is 1
B) is 2
C) is 3
D) is 4
16. How many methine groups are there in isopropylcyclopentane?
A) one
B) two
C) three
D) four
E) five
Page 5

17. Cyclohexane adopts the chair conformation rather than a planar structure because:
(A) Torsional strain is minimized
(B) The C

C

C bond angles are close to 109.5
0
.
(C) There are no 1,3-diaxial interactions in a planar structure.
A) only A
B) only B
C) A and B
D) A, B, and C
18. Which of the following undergoes S
N
1 solvolysis in ethanol/water at the fastest rate?
O
OTs F Br
1) 2) 3) 4)
A) is 1
B) is 2
C) is 3
D) is 4
OCCH
3
19. Which of the following cannot undergo an E2 reaction?
H
3
C CH
2
Br H
3
C Br
CH
2
Br
CH
3
CH
3
A B C
A) A
B) B
C) C
D) none (all can undergo an E2 reaction)
20. Consider the reaction of each of the following with 1-bromopentane. Which one would have the highest elimination/substitution ratio?
A) NaOCH
2
CH
3
, ethanol, 55
0
C
B) NaSH, ethanol-water, 25
0
C
C) KOC(CH
3
)
3
, (CH
3
)
3
COH, 55 0 C
D) KCN, DMSO, 40
0
C
Page 6

21. What is the major product of the following reaction?
Br
H
3
C
CH
3
NaOCH
2
CH
3
CH
3
CH
2
OH
H
OCH
2
CH
3
H
3
C
CH
3
1) 3)
H
H
3
C
H
CH
3
CH
3
CH
2
H
3
C
H
3
C
H
H
A) is 1
B) is 2
C) is 3
D) is 4
22. What is(are) the product(s) in the Pd-catalyzed hydrogenation of 1,2dimethylcyclopentene?
A) trans -1,2-dimethylcyclopentane
B) cis -1,2-dimethylcyclopentane
C) a mixture of trans and cis -1,2-dimethylcyclopentane
D) 1,1-dimethylcyclopentane
23. Which of the following undergoes a substitution reaction with sodium cyanide in
DMSO at the fastest rate?
A) CH
3
CH
2
F
B) CH
3
CH
2
Cl
C) CH
3
CH
2
Br
D) CH
3
CH
2
I
Page 7

24. Including E/Z isomers, how many E2 products are possible in the following reaction?
KOC(CH
3
)
3
(CH
3
)
2
CHCHCH
2
CH
3
Br
(CH
3
)
3
COH
A) one
B) two
C) three
D) four
E) five
25. Which of the following is the most stable radical?
1) CH
3
CH
2
CCH
3
2) CH
3
CH
2
CCH
2
3) CH
3
CHCCH
3
4) CH
2
CH
2
CCH
3
CH
3
CH
3
CH
3
CH
3
A) is 1
B) is 2
C) is 3
D) is 4
26. Which of the molecules below are chiral?
HO OH HO OH HO
A B C
A) only A
B) A and C
C) B and C
D) A, B, and C
Br
27. Arrange the following alcohols in order of their decreasing reactivity with HBr
(most reactive first).
H
3
C OH
CH
2
OH CH
3
OH
A B C
A) A>B>C
B) A>C>B
C) C>A>B
D) B>C>A
Page 8

28. Identify the mechanistic pathways, respectively, for the products in the following reaction.
CH
3
CH
2
CH
2
CH
2
CH
CH
3
3
ONa
Br CH
3
OH
CH
2
CH=CH
2
+ CH
3
CH
2
CH
2
CH
2
OCH
3
A) E1, S
N
1
B) E1, S
N
2
C) E2, S
N
1
D) E2, S
N
2
29. Which of the following are the chain propagating steps in the free radical chlorination of methane?
A. Cl
2
2Cl
B. Cl
2
+ H 2HCl + Cl
C. CH
4
+ Cl CH
3
+ HCl
D. CH
4
+ H CH
3
+ H
2
E. CH
3
+ Cl
2
CH
3
Cl + Cl
F. CH
3
+ Cl CH
3
Cl
A) A and C
B) B and F
C) C and D
D) C and E
30. Which of the following alkenes is expected to have the highest heat of hydrogenation?
A) 1-pentene
B) trans -2-pentene
C) cis -2-pentene
D) 2-methyl-2-butene
31. What is the product of the following reaction? BrCH
2
CH
2
CH
2
CH
2
OH + SOCl
2

A) ClCH
2
CH
2
CH
2
CH
2
OH
B) ClCH
2
CH
2
CH
2
CH
2
Cl
C) BrCH
2
CH
2
CH
2
CH
2
Cl
D) ClCH
2
CH
2
CH
2
CH
2
SOCl
Page 9

32. Studies indicate that the methyl radical is trigonal planar. Based on this, which of the following best describes the methyl radical?
A) The carbon is sp 2 hybridized and the unpaired electron occupies an sp 2 orbital.
B) The carbon is sp
2
hybridized and the unpaired electron occupies a 2p orbital.
C) The carbon is sp
3
hybridized and the unpaired electron occupies an sp
3
orbital.
D) The carbon is sp 3 hybridized and the unpaired electron occupies a 2p orbital.
33. Identify the relationship between the following two Newman projections.
H
3
C
CH
3
H H
3
C
H
H and
H H H
3
C
CH
3
A) identical
B) stereoisomers
C) different conformations of the same compound
D) constitutional isomers
CH
3
H
34. What is the total number of constitutional isomers with the formula C
5
H
12
?
A) only one
B) two
C) three
D) four
E) five
35. Which of the following is isobutyl alcohol?
A) CH
3
CH
2
CH
2
CH
2
OH
B) CH
3
CH
2
CH(OH)CH
3
C) (CH
3
)
2
CHCH
2
OH
D) (CH
3
)
3
COH
36. The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via :
A) syn addition
B) anti addition
C) Markovnikov addition
D) anti-Markovnikov addition
Page 10

37. What is the relationship between the following two molecules?
HO H H OH and
H
3
C CH
3
H
3
C CH
3
A) identical
B) diastereomers
C) enantiomers
D) constitutional isomers
38. Which reaction below gives a pair of diastereomers?
O
H CH
3
CH
3
COOH
1) 3)
CH
3
1) BH
3
-THF
2) H
2
O
2
, NaOH
H CH
3
HBr
2) 4) peroxides
A) is 1
B) is 2
C) is 3
D) is 4
39. What is the IUPAC name of the following:
CH
3 HBr
A) 3-propylpentane
B) 3-ethylhexane
C) 2-ethylheptane
D) 4-ethylpentane
Page 11

40. Which of the following is tert -butyl chloride?
A) CH
3
CH
2
CH
2
CH
2
Cl
B) CH
3
CH
2
CHClCH
3
C) (CH
3
)
2
CHCH
2
Cl
D) (CH
3
)
3
CCl
41. Give the total number of stereoisomers of 2,3-dibromobutane.
A) none, only a single structure
B) two
C) three
D) four
42. What is the IUPAC name of the following?
A) 1-ethyl-4,4-dimethylcyclopentane
B) 1-ethyl-3,3-dimethylcyclopentane
C) 3-ethyl-1,1-dimethylcyclopentane
D) 4-ethyl-1,1-dimethylcyclopentane
43. Starting with 1-methylcyclohexene, which of the following reaction sequences is the best synthesis of the azide shown below?
CH
3
N
H
N
H
N
A) (1) HBr (2) NaN
3
B) (1) HBr, peroxides (2) NaN
3
C) (1) B
2
H
6
, diglyme (2) H
2
O
2
, OH
-
(3) TsCl, pyridine (4) NaN
3
D) (1) CH
3
CO
3
H (2) NaN
3
(3) H
2
SO
4
, heat (4) H
2
/Pt
44. How many stereoisomers are there of 1-isopropyl-4-methylcyclohexane.
A) only 1 structure possible - no stereoisomers
B) two
C) three
D) four
Page 12

45. The sawhorse drawing of butane below is:
H
H
H
H
CH
3
CH
3
A) a gauche conformation
B) the anti conformation
C) the least stable eclipsed conformation
D) the most stable eclipsed conformation
46. Identify the relationship between the following two structures.
CH
3
CH
3
H
H
3
C
H and H
H
CH
3
H
CH
3
CH
3
H
A) constitutional isomers
B) stereoisomers
C) different conformations of the same compound
D) idential
47. Which of the following does not give 1,2-dimethylcyclohexene as one of the acidcatalyzed dehydration products?
CH
2
OH
CH
3
H
3
C CH
3
OH
H
3
C OH
CH
3
H
3
C CH
2
OH
1) 2) 3) 4)
A) is 1
B) is 2
C) is 3
D) is 4
Page 13