Exam 2
Exam 2
Exam 2
Exam 2A
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ORGANIC CHEM 2423 EXAM # 2A Sample(Chapters 5,6, and7)
Name:__________________
Score
DIRECTIONS- Please answer all questions in the space provided as completely and clearly as possible .
Show all your work for the writing portions of the exam.
OH
..
.. O:
O: ..
+ : CN CN
_____ 4. This process occurs when both bonding electrons remain with one product fragment.
_____ 6. Provide the proper IUPAC name for the alkene shown below.
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_____ 7. What is the acceptable structure for 1,2-dimethylcyclohexene?
B. C D.
A.
_____ 8. What two atomic orbitals or hybrid atomic orbitals overlap to form the C = C bond in ethene?
A. B.
C. D.
OH
O
CO2 +
3
_____15. What is the major of the following reaction?
OH
H2SO4 /heat
CH3
A. B. C. D.
CH2 CH3
CH3
I II III
I. _______________________________________
II. _______________________________________
III. ______________________________________
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17. ( 5 points) Show by a series of reactions how could you prepare the following compounds from the
indicated starting compound. Be sure to clearly indicate the reagents used in each step.
Cl
Cl
18. ( 5 points) Propose a mechanism to account for the shown product. Please show the structures of
the intermediates and using curved arrows to indicate electron flow in each step.
(Rearrangement may occur)
CH3
ether
CH3 - C - CH = CH2 + HBr
CH3
19. (5 points) Give the average bond dissociation enthalpies below, calculate the enthalpy change for
the following reaction.
OH
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20. Predict the major product of the following reactions. (2 points each)
CH3
Br2 /H2O
a) CH3 - CH - CH = CH2
CH3 H2
b)
Pd /C
HBr /ether
c)
1) BH3, THF
d)
2) H2O2 , OH
Br
e) KOH/ ethanol
KMnO4
f) 2 - hexene
H3O
2 moles H2
g) CH2
Pd /C
h) Br2 / CCl4
i) CH2I2 / Zn(Cu)
j)
1) O3
2) Zn / H3O
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Bonus Question ( 10 points) – Please show all your work for complete credit.
CH3 CH3
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ORGANIC CHEM 2423 EXAM # 2A Sample Exam - Answers
1. C 2. C 3. B 4. B 5. B 6. C 7. B
8. B 9. D 10. A 11. B 12. A 13. B 14. C
15. B
b)
(2Z)- 3-methyl-2-pentene 2,3-dimethyl-1-cyclopentene
CH3 H
CH3
C=C
CH3-CH2 CH3
CH3
17. ( 5 points) Show by a series of reactions how could you prepare the following compounds from the
indicated starting compound. Be sure to clearly indicate the reagents used in each step.
Cl
Cl
CHCl3 /KOH
Cl2 /light
Cl
KOH /ethanol
18. ( 5 points) Propose a mechanism to account for the following reaction. Please show the structures of
the intermediates and using curved arrows to indicate electron flow in each step.
(Rearrangement may occur)
CH3
CH3 CH3 Br
ether
CH3 - C - CH = CH2 + HBr CH3 - C - CH - CH3 :Br
CH3 - C - CH - CH3
CH3 CH3
3 carbocation intermediate
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19. (5 points)Using average bond dissociation enthalpies table, calculate enthalpy change for the
following reaction. (C-H)
20. Predict the major product in each of the following reactions. (2 points each)
OH
CH3 CH3
Br2 /H2O
a) CH3 - CH - CH = CH2 CH3 - CH - CH - CH2Br
CH3 H2
b) CH3
Pd /C
HBr /ether
c)
Br
1) BH3, THF
d) OH
2) H2O2 , OH
Br
e) KOH/ ethanol
g) 2 moles H2
CH2 CH3
Pd /C
H
h) Br2 / CCl4 Br
Br
CH3
i) CH2I2 / Zn(Cu)
O O
j) O3
CH3 C - (CH2)4 - C -H
H3O
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Bonus Question ( 10 points) – Please show all your work for complete credit.
I) Initiation : Cl - Cl Cl . + Cl .
II) Prpagation .
a) Cl . + CH3 - CH2 - CH - CH3 CH3 - CH2 - C - CH3 + HCl
CH3 Cl CH3
b) .
CH3 - CH2 - C - CH3 + Cl2 CH3 - CH2 - C - CH3 + Cl .
CH3 CH3
III) Termination
a) Cl . + Cl . Cl2 Cl
.
b) CH3 - CH2 - C - CH3 + Cl . CH3 - CH2 - C - CH3
CH3 CH3
CH3 CH3
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Chemistry 2423
Exam 2B
NH2
N O
HO
O
H H
H H
OH H
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ORGANIC CHEM 2423 EXAM # 2B Sample Name:__________________
Score
DIRECTIONS- Please answer all questions in the space provided as completely and clearly as possible .
Show all your work for the writing portions of the exam.
_____1. For which of the following compounds does radical chlorination give a single monochloro product?:
A) Radical reaction is a process involving symmetrical bond breaking and bond making.
B) Endergonic reaction is a reaction where G is negative.
C) Substitution is a reaction where two reactants exchange parts to give two new products.
D) Activation energy is the energy needed by reactants to reach the transition state.
_____6. Use the following bond dissociation Energies in the table below to calculate Hfor
the reaction of ethyl methyl ether with hydrogen chloride and hydrogen iodide.
D (kJ/mol)
_____7. From the above data of Haand Hb (refer to question 6): which acid would you predict to be most
effective for the formation of ethanol?
A) HCl B) HI C) both acids D) cannot predict
_____8. The reaction depicted in the energy diagram below can best be described as:
____10. Ocimene is a triene found in the essential oils of many plants. What is its IUPAC name, including
stereochemistry?
A) (3Z)-3,7-dimethyl-1,3,6-octatriene B) (3E)-3,7-dimethyl-1,3,6-octatriene
C) (5Z)-2,6-dimethyl-2,5,7-octatriene D) (5E)-2,6-dimethyl-2,5,7-octatriene
____11. A neutral molecule containing a divalent carbon with six valence electrons is called:
____12. Arrange the following bicyclic alkenes in order of increasing stability (least stable to most stable).
A) III < II < I B) I < II < III C) I < III < II D) II < III < I
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____13. Which of the following alkene has the E configuration?:
CH3
CH3
CH3
(I) (II) (III)
____ 14. Arrange the following carbocations in order of increasing stability (least stable to most stable).
I II III
A) III < II < I B) I < II < III C) I < III < II D) II < III < I
Cl
Cl OH OH
Cl Cl
A) B) C) D)
____17. Suggest structure (s) for alkene (s) that give the indicated reaction product.
H2
?
Pd
CH3
H2SO4/heat
____19. What alkene would you start with to prepare the 2,4-diiodopentane below:
A): B):
C): D):
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ii) The First Step of the Reaction:
Label the nucleophile, Nu, and the electrophile, E+, in the blanks provided under the reactant
structures (Second and Third Steps).
iv) Draw arrows on the structures above showing electron flow in Second and Third Steps of this
reaction.
a. Using the bond dissociations values in the table below, calculate the H for this reaction. Show your
calculations for full credit.
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b. Draw a qualitative reaction energy diagram for the reaction of 2-bromo-2-methylpropane with water.
The first step is the slowest step of the reaction. Fully label the diagram, including the coordinates.
23. Propose a mechanism, showing the structures of the intermediates in the following
reaction:
Cl
+ HCl
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24. Predict the major product of each reaction. Indicate regiochemistry and stereochemistry when relevant.
25. What reagent would you use to carry out each of the following transformations? In each reaction place the
reagent above the arrow.
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BONUS QUESTION(10 points)- Show all your work.
In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound
A: C7H12." Government agents have offered you a considerable sum to determine the structure of this
compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with
1 mol equiv of hydrogen and, after treatment with acidic KMnO4, gives the dicarboxylic acid C (see below).
Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with
1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO4.
ii) What was the other product formed in the KMnO4 oxidation of B?
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ORGANIC CHEM 2423 EXAM # 2B Sample Exam - Answers
PART I :
1. C 2. A 3. B 4. B 5. C 6. B
7. B 8. B 9. A 10. B 11. C 12. D
13. A 14. D 15. B 16. C 17. D 18. B
19. B 20. D
PART II :
21. i)
iv)
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22. a.
23.
Cl
+ H-Cl
H H
+
+
Hydride Cl-
Cl-
shift
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24.
25.
1. BH3, THF
2. H2O2, NaOH, H2O
OH
1. Hg(OAc)2, H2O
2. NaBH4 OH
CH2I2, Zn(Cu)
O
1. O3 H
2. Zn, H3O+ CH3
O
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BONUS QUESTION:
i) D.U. = 1 + C –1/2(H + X – N)
= 1 + 7 – 1/2(12)
=2
Compound A possesses 2 degrees of unsaturation:
iii) The other product formed in the KMnO4 oxidation of B is: CO2
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