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CHE 231

Fall 2005
Final Exam
1. Which of the following substances cannot function as a Lewis base? (Lone pairs of electrons have been
omitted from these drawings).
1.
2.
3.
4.
5.

2.

For which of the following compounds is cis-trans isomerism possible?


1.
2.
3.
4.
5.

3.

OH
NH3
BH3
Br
All of the compounds above will function as a Lewis base.

1-butene
1-methylcyclohexene
2-heptene
1-butene and 1-methylcyclohexene
1-methylcyclohexene and 2-heptene

How many isomers (configurational isomers and stereoisomers) are possible for 1,2dimethylcyclopropane?
1.
2.
3.
4.
5.

three
four
five
six
ten

4. Which of the alkenes below would be most stable?


1)

2)

3)

5. The correct name for the hydrocarbon shown below is:


CH3
H

1.
2.
3.
4.
5.

(2Z, 4Z)2,4heptadiene
(2E, 4Z)2,4heptadiene
(2E, 4E)2,4heptadiene
trans ,trans2,4heptadiene
None of the above

C C

CH2CH3
C C
H
H

4)

5)

6. Which equation correctly describes the kinetics of the E2 reaction?


1.
2.
3.
4.
5.

Rate = k[substrate][base]
Rate = k[substrate]
Rate = k[base]
Rate = k[substrate]2[base]2
Rate = k[substrate]2

7. Which halide in each of the pairs to the right will react most rapidly by the SN1 pathway?
CH3
CH3CCH3

1.
2.
3.
4.

or

Cl

A and C
A and D
B and C
B and D

CH3
CH3CCH3
Br

CH3

CH3

Br

Br

or
C

8. Which would rotate the plane of plane-polarized light?

1)

CH3CH2

OH
C CH2CH3

2)

CH3

CH3

4) An equimolar mixture of

3) An equimolar mixture of

CH3CH2

CH3
H
OH
H
OH

OH
OH
and
C CH3
CH3 C CH2CH3
CH3

CH3

CH3
HO
H
and
H
OH
CH3

9. The correct configuration at the two centers of chirality in the molecule below would be:

1.
2.
3.
4.

(2S, 3S)
(2R, 3S)
(2S, 3R)
(2R, 3R)

CH3
H
CH3

OH
Br
H

CH3
H
OH
H
OH
CH3

10. Which compound has an (R)- configuration?


O
C OH
OH
1) H
CH3

O
C OH
2) HO
H

OH
O S O
Cl
4) Br
H

O
C H
3) HO
H

CH3

CH3

11. What are the formal charges on the atoms in the following species?

1.

O = 1

N=0

2.

O=0

N = +1

O=0

3.

O = +1

N=0

O = +1

4.

O = 1

N = 1

O = 1

5.

O=0

N=0

O=0

5)

C(CH3)3
H
D

..
..
O N O
..
..

O = 1

12. Reaction of trans-2-butene with ozone followed by treatment with zinc and acetic acid would yield:
4) CH3CH2OH

1) two moles of CH3CH2OH


2)

O
two moles of CH3C OH

O
and CH3C OH

O
O
5) CH3C OH and CH3C H

O
two
moles
of
CH
3)
3C H

13. One factor that does not affect the rate of a chemical reaction is:
1.
2.
3.
4.
5.

the free energy change during the reaction


the number of collisions in a unit volume and unit time
the free energy of activation
the temperature
the probability that the reactants will be properly oriented upon collision

14. Which drawing represents the lowest energy structure for a dimethylcyclohexane?
CH3

CH3

1)

CH3

CH3
2)

3)
CH3
CH3

CH3
4)

CH3

5)

3
CHCH
3

(1 mole of each)

(1 mole of each)

Questions 15 19 refer to the graph below:

15. Which arrow represents the free energy of reaction, Grxn?


1) A

2) B

3) C

4) D

5) E

16. Which arrow represents the free energy of activation, G, for the slowest (or rate determining) step?
1) A

2) B

3) C

4) D

5) E

17. Which arrow represents the formation of the least stable species represented on the graph?
1) A

2) B

3) C

4) D

5) E

18. Which arrow represents the formation of a reaction intermediate?


1) A

2) B

3) C

4) D

5) E

19. The graph above would best describe the energy changes for which reaction listed below?
1.
2.
3.
4.
5.

The SN2 reaction of iodide ion with chloromethane


The SN1 reaction of iodide ion with 2-methyl-2-chloropropane
The reaction of propene with BH3 to add boron and hydrogen across the double bond
The E2 dehydrohalogenation of 1-iodopropane using a strong base
None of the above

20. What is the correct name of the compound shown to the right, below?
1.
2.
3.
4.
5.

CH3

2,3-dimethylbicyclo[4.3.2]nonane
8,9-dimethylbicyclo[0.3.4]nonane
4,5-dimethylbicyclo[4.3.0]nonane
2,3-dimethylbicyclo[4.3.0]nonane
1,2-dimethylbicyclo[4.3.0]nonane

CH3

21. Which of the following molecules would have a dipole moment equal to zero?
1) CH2Cl2

b) CH3F c) H2O

d) NH3

e) BF3

22. What are the hybridizations of the carbon atoms in the molecule shown below, starting at carbon #1?

1.

sp3

sp2

sp2

sp2

2.

sp2

sp2

sp

sp2

3.

sp3

sp2

sp

sp2

4.

sp3

sp

sp

5.

sp

sp

sp

C C C

HO CH2 2

H
H

sp
2

sp

23. Which compound below is not an isomer of the others?


CH2
1)

2)

3) CH3CH2C CCH3

4) CH3CH CHCH2CH3

5) CH2 CH CH CH CH3

24. Which alkenes have (Z)- configurations?


Cl
CH3

C C

Br

Br

1.
2.
3.
4.
5.

C C

CH3

Br

CH2CH3

C C

CH3
CH3CH

Cl
I

CH3

C C

CH3
CHCH3

(CH3)3C

CH2CH3

CH3CH2

C C

D
H

B and E
A and B
C and D
B, D, and E
C, D, and E

25. What is the major product, D, of the following series of reactions?

H C C H

NaNH2

anhydrous liquid

CH3I

NH3

1) CH2
Br

Br
CH2

2) CH3CHCH3
Br

H2
Lindlar Catalyst

3)

CH3
H

C C

CH3

H
Br

4)

HBr

no peroxides

C C

Br
H

5) CH3CH2CH2 Br

26. What radical is most likely to be formed as an intermediate in the following reaction?

CH3
CH3CH2CCH3
CH3

Br2

. CH3

CH3
. 2CH2CCH3
1) CH
CH3

CH3
3) CH3CH2CCH3
CH
. 2

CH3CHCCH3
CH3

2)

CH3
4) CH3CH2CCH2.
CH3

. CH

5) CH3CH2CCH3

CH3

27. What is the formal charge on nitrogen in the following species?


1.
2.
3.
4.
5.

:O :
..
CH3 N O.. :

+2
+1
0
1
2

28. What is the major product of the following reaction?


CH3
CH3CHCH CH2

1)

HBr

CH3
CH3CHCHCH3
Br

no peroxides

2)

CH3
4) CH3CCH2CH3

5)

Br

CH3 Br
CH3CHCHCH2
Br

3)

CH3
Br CH2CHCH2CH3

CH3
CH3CHCH2CH2 Br

29. Which compound would not exhibit optical activity?


O
C OH
H
H

O
C OH
H
OH

H
H
H

H
H
H

OH
H
H
C OH
O
1)

H
OH
OH
C OH
O
2)

O
C OH
H
OH
HO
HO
HO

H
H
H
C OH
O
3)

O
C OH
HO
H
H
H

H
OH
OH
OH
C OH
O
4)

O
C OH
H
OH
H
H
H

H
H
OH
C OH
O
5)

30. What is the stereochemical result of radical bromination at carbon 3 of the following compound?
CH3
(R)- CH3CH2CCH2CH2CH3
H

1.
2.
3.
4.
5.

UV

Br2

radiation

A pair of enantiomers is formed.


A pair of diastereomers is formed.
A single meso compound is formed.
A single compound with an (R)-configuration is formed.
A single compound with an (S)-configuration is formed.

31. What is the major product of the following E1 elimination?


CH3

H2SO4
heat

OH

CH3

CH3
1)

2)

CH3
3)

CH3
4)

32. Which reaction will not proceed to the right to produce appreciable amounts of tert-butoxide ion
((CH3)3CO) as a product?

1) (CH3)3COH + NaH
2) (CH3)3COH + Na
3) (CH3)3COH + NaOH
4) (CH3)3COH + NaNH2
5) (CH3)3COH + K
33. Which of the following structures are important resonance contributors to the species below?
:O :

..
:O :

:O :

CH3 C CH3

CH3 C CH3

CH3 C
.. CH3

1.
2.
3.
4.
5.

A and C
A and B
B and C
A, B, and C
None are important contributors.

CH2
5)

34. The best method of preparing 3-bromocyclohexene from cyclohexene is:


Br
???

Br2

1)

2)

Sn2

NaBr

conditions

CCl4
PBr3

3)

NBS, light

4)

heat

CCl4

HBr

5)

no peroxides

35. The major product of the following E2 elimination is:


H
C

Cl
C CH
3
CH2CH3

CH3
CH3CH2

CH3

1)

CH3

2)

C C
CH3CH2

CHCH3
C C

CH3CH2CH
CH3

CH3

CH3

CH2CH3
C C

CH3CH2

CH2CH3
CH3

3)

strong base

CH3

a.) N = +1, C = 0, S = -1
b.) N = -1, C = -1, S = +1
c.) N = +1, C = 0, S = -2
d.) N = -1, C = 0, S = 0
e.) None of the above.

CH2CH3
C C

4)

CH3CH2CH
CH3

36. The correct formal charges for the atoms in the thiocyanate anion are:

CH3

CH2

37. Rank the following resonance structures in order of the amount of their contribution to the overall
resonance hybrid (least important contributor to most).

CH

NH

NH

CH3

CH

CH2

NH

CH3

B
a.)
b.)
c.)
d.)

e.)

CH3

CH

CH2

CH2

CH

NH
C

CH3

CH2

A less important than B less important than C less important than D.


C less important than B less important than D less important than A.
B less important than C less important than D less important than A.
B less important than D less important than C less important than A.
None of the above.

38. Which of the following pairs of structures do not represent resonance structures?

a.)
CH3

O
C

b.)
CH3

c.)

O
CH3

CH3

CH3
O

d.)
CH3
H

e.) All of the above pairs represent resonance structures.

39. The triple bond in acetylene is made up of

a.) One sigma bond and two pi bonds.


b.) One pi bond and two sigma bonds.
c.) Three sigma bonds.
d.) Three pi bonds.
e.) None of the above.

CH3
O

C
O

O
N

O
CH3

C
O

C
O

40. Which of the following pairs of structures represent(s) stereoisomers?

a.) H F

H
F
H

b.)
H

and

F
F and

F
c.)
H

and H

d.) All of the above represent pairs of stereoisomers.


e.) Pairs (a) and (c) represent stereoisomers, but not pair (b).

41. Rank the following compounds from lowest to highest boiling point.

CH3 CH3

CH3

C
a.)
b.)
c.)
d.)
e.)

CH3

CH

CH3

CH3

O D
CH3CH 2CH2CH3

CH3

C
CH3

CH2CH 3

A lower than B lower than C lower than D.


B lower than C lower than A lower than D.
C lower than B lower than A lower than D.
C lower than B lower than D lower than A.
None of the above.

42. Which of the following is the most stable conformation of cis-1-isopropyl-4-methylcyclohexane?

CH(CH3)2

a.)

b.)

CH(CH3)2
c.)

CH3

CH(CH3)2
CH3

CH3

d.)
CH3

CH(CH3)2

43. Which of the following will be polar?


a.) CO2
b.) SO2
c.) SO3
d.) All of the above.
e.) Choices (b) and (c), but not (a).

e.) None of the above

F
H

44. Rank the following acids in order of increasing acidity (least acidic to most).

O
CH3CH 2CH2NH 2

CH3CF 2C-OH

A
a.)
b.)
c.)
d.)
e.)

O
CH3CH 2C-OH

CH3CH 3CH2OH
D

A less acidic than C less acidic than B less acidic than D.


D less acidic than C less acidic than B less acidic than A.
A less acidic than D less acidic than C less acidic than B.
B less acidic than C less acidic than D less acidic than A.
None of the above.

45. The graph below represents a conformational analysis for which of the following?

a.)
b.)
c.)
d.)
e.)

Rotation about the C1-C2 bond in propane.


Rotation about the C1-C2 bond in butane.
Rotation about the C1-C2 bond in 1-chlorobutane.
Rotation about the C1-C2 bond in 2-chlorobutane.
None of the above.

Questions 46-48 concern the following four structures:

CH3

CH3
H

Br

Br

Br

CH3

II

CH3
H

Br

CH3

III

CH3
Br

Br

CH3

Br

Br

IV

H
H
CH3

46. Which pair of structures represent entatiomers?


a.) I and II.
b.) I and III.
c.) I and IV.
d.) II and III.
e.) Both (c) and (d).
47. For which compound are both stereocenters in the (S) configuration?
a.) I.
b.) II.
c.) III.
d.) IV.
e.) none of the above.

48. Which of the following pairs will have different melting points?
a.) I and II.
b.) I and III.
c.) I and IV.
d.) II and III.
e.) Both (a) and (b).
49. Which of the following will always be true for the (R) enantiomer of a compound with one tetrahedral
stereocenter?
a.) The compound is chiral..
b.) The compound is dextrarotatory.
c.) The compound is levrorotatory.
d.) Both (a) and (b).
e.) Both (a) and (c).
50. What is the index of hydrogen deficiency for the following compound?

CH3

CH3
a.) 1

b.) 2

c.) 3

d.) 4

e.) Cant be determined from the information given.

51. What will be the major organic product from the following reaction?

H2O, H+

CH3

a.)

OH
CH3

b.)

c.)
CH3

d.)
CH3

OH

CH3

OH

OH

e.) a 50:50 mixture of (c) and (d).


52. What will be the major organic product from the following reaction?

CH3

a.)

OH
CH3
Br
+ enantiomer

e.) None of the above.

Br2, H2O

b.)

?
Br
CH3

OH
+ enantiomer

c.)

Br

d.)

OH
CH3

CH3
OH
+ enantiomer

Br
+ enantiomer

53. Which of the following SN2 reactions will not proceed to any appreciable extent?
DMSO
CH3-CN + NaI
a.) NaCN + CH3-I

Acetone

b.) NaI + CH3-Br

CH3-I + NaBr

CH3OH

c.) NaOCH 3 + CH 3Cl

CH3-OCH3 + NaCl

Acetone

d.) NaI + CH3OH

CH3-I + NaOH

e.) All of the above will proceed to completion.


54. Which of the following reactions will yield an optically active product?

a.)

Br2/CCl4

trans-2-butene

Br2/H2O

b.) trans-2-butene

1.) OsO 4

c.) trans-2-butene

2.) NaHSO3, H2O


1.) O 3, -78C

d.) trans-2-butene

2. Zn, HOAc
e.) None of the above.

55. Which of the following will provide the best synthesis for (E)-2-methyl-3-hexene?

a.)

b.)

c.)

NaNH2

NaNH2

NaNH2

CH3CH 2Br

H2/Lindlar's catalyst

Br
Na, liquid NH3

CH3CH 2Br

Na, liquid NH3

d.) All of the above a viable syntheses for (E)-2-methyl-3-hexene.


e.) Both (b) and (c) are viable syntheses for (E)-2-methyl-3-hexene.

56. What will be the major substrate-derived product in the following reaction?

CH3

Br +

DMSO

NaSCH 2CH 3

room temperature

CH3
b.)

a.)
CH3

SCH2CH3

CH3

SCH2CH3

CH3

CH3

c.)

d.)
CH3

CH3

CH3
e.) A mixture of products (a) and (b).
57. By which mechanism will the product in problem 56 be formed.
a.) SN1
b.) SN2
c.) E1
d.) E2
e.) a mixture of (a) and (c).
58. What will be the organic product of the following transformation?

1.) OsO 4

2.) NaHSO3/H2O

a.)
OH

c.)

b.)
HO

OH

OH
HO

d.)
H

OH

e.) A 50:50 mixture of (a) and (b).


H

59. What will be the major substrate-derived product in the following reaction?

CH3

Br +

CH3CH2OH

NaOCH2CH3

reflux

CH3
b.)

a.)
CH3

OCH2CH3

CH3

OCH2CH3

CH3

CH3

c.)

d.)
CH3

CH3

CH3
e.) A mixture of products (a) and (b).
60. By which mechanism will the product in problem 59 be formed.
a.) SN1
b.) SN2
c.) E1
d.) E2
e.) a mixture of (a) and (c).
61. What will be the final organic product of the following reaction?

H2O, H2 SO4

HgSO4
a.)

b.)

OH

c.)
OH

OH
e.)

d.)

O
H

62. What will be produced in the following reaction?

CH3

CH2CH 3
I
+ CH 3OH

a.)

CH2CH 3
OCH3

CH3

HI +

b.)
CH3O

c.)

CH2CH 3
CH3

CH3

CHCH3
C

d.) All of the above


e.) (a) and (b), but not (c).
63. What will be the final product Z of the following reaction sequence?

CH3
C

CH 2CH3

TsCl
pyridine

OH

a.)

CH3

DMF

CH3

b.)
C

CH 2CH3

NaSH

HS

SH

H
c.)

CH3
C

CH 2CH3

CH2CH 3
H

OTs

d.)

CH3
C

CH 2CH3

Cl

e.) A 50:50 mixture of (a) and (b).


64. Which of the following will perform the following transformation in high yield?
Cl
OH

a.) HCl
b.) SOCl2/pyridine
c.) TsCl
d.) All of the above will perform this transformation
e.) Both (a) and (b), but not (c).

65. Which of the following alcohols will undergo dehydration the most rapidly?

b.)

a.)

OH

OH

c.)

d.)
HO

CH3OH

e.) None of the above alcohols will undergo dehydration.


66. What would be the best method of performing the following transformation?

OH

?
a.) Hg(OAc)2 and H2O, followed by NaBH4
b.) BH3, followed by H2O2 and NaOH
c.) H2O and H2SO4
d.) H2O and peroxides
e.) OsO4 followed by NaHSO3.
67. What will be the final product K of the following reaction sequence?

CH 3CH2CH

CH2

a.) CH CH CH
3
2

HBr

peroxides

CH3

NaCN

DMSO

b.)
CH3CH 2CH2CN

c.)
CH3CH 2CH2CH2CN

CN
d.)

CH3CH 2C
CN

CH2

e.)

CH3CHCH
CN

CH2

68. What will be the final product N of the following reaction sequence?

CH 3CH2CH

NBS

CH2

CCl4

a.) CH CH CH
3
2

NaCN

DMSO

c.)
CH3CH 2CH2CH2CN

b.)
CH3CH 2CH2CN

CH3

CN
d.)

CH3CH 2C

e.)
CH2

CH3CHCH

CH2

CN

CN
Questions 69-70 concern the following infrared spectrum:

69. The broad absorbance at 3500 cm-1 corresponds to


a.) a C-H stretching vibration.
b.) an O-H stretching vibration.
c.) a C=O stretching vibration,
d.) A terminal alkyne C-H bending vibration.
e.) A nitrile C-N stretching vibration.
70. The above spectrum characterizes which of the following compounds?

a.)

b.)

CH3

CH2
OH

c.)

NH2

d.)
HO

CN

OH

e.)
C

CH