CH221 ORGANIC CHEMISTRY I
QUIZ 3
27 APRIL 2009
Time allowed: 50 minutes
Attempt all 35 questions on the grid answer sheet provided
1.
Which of the following reagents adds to an alkene in an antiMarkovnikov fashion?
A.
B.
C.
D.
2.
H2O/H+
HBr
HCl
[1] BH3; [2] H2O2/OH-
In which of the following reactions will carbocation
rearrangements occur?
A.
The addition of Br2 and H2O to a C
Chalohydrin formation.
B.
The addition of Br2.
C.
The addition of H2O in the presence of acid.
D.
Reactions (The addition of Br2 and H2O to a C Chalohydrin formation) and (The addition of H2O in the
presence of acid) will both show carbocation rearrangements.
E.
Reactions (The addition of Br2 and H2O to a C Chalohydrin formation), (The addition of Br2 ), and (The
addition of H2O in the presence of acid) will all show
carbocation rearrangements.
3.
A compound M with molecular formula C8H12 and no triple
bonds reacts with H2 to give a new compound having
molecular formula C8H14. What can be said about compound
M?
A.
Compound M has 3 rings.
B.
Compound M has 2 rings and 1  bond.
C.
Compound M has 1 ring and 2  bonds.
D.
Compound M has 3  bonds.
E.
It's impossible to say anything about the structure of
compound M given this data.
4.
7. Which is not a product of this reaction?
8.
What is the missing reagent in the reaction below?
9. From the list of possible carbocations, which one would not be
likely to rearrange?
10. You are to synthesize 2-bromobutane from 1-butene. You must
get the highest yield possible. From the list of reagents given
below, which one would you use to obtain the greatest yield?
A.
B.
C.
D.
E.
Alcoholic KOH
KOH and water
t-Butyl alcohol and (CH3)3COK
Ethanol and CH3CH2ONa
Methanol and CH3ONa
11. Give the IUPAC name for the following compound.
Predict the product(s).
12. What is the missing reagent in the reaction below?
5.
Predict the product(s).
6.
Predict the product(s).
13. What is the product in the reaction below?
1
14. Determine the product in the reaction below.
23. Which of the following alcohols undergoes dehydration most
slowly on treatment with acid?
15. Determine the product in the reaction below.
16. Determine the major product in the reaction below.
17. Predict the product in the reaction below.
18. Determine the product in the reaction below.
24. For the compound drawn below, decide which statement(s) is
(are) true.
A.
It is soluble in H2O.
B.
It is soluble in CHCl3.
C.
It contains a sp hybridized atom.
D.
The statements (It is soluble in H2O) and (It is
soluble in CHCl3) are both true.
E.
None of the choices are correct.
25. Which of the following statements is (are) true about ring
opening of epoxides with nucleophiles?
19. Determine the product in the reaction below.
20. Which of the following compounds has the highest boiling
point?
A.
All nucleophiles ring open epoxides with backside
attack.
B.
Ring opening of epoxides always follows an SN2
mechanism.
C.
Nucleophilic attack always occurs at the less
substituted carbon atom.
D.
Statements (All nucleophiles ring open epoxides with
backside attack) and (Ring opening of epoxides always
follows an SN2 mechanism) are true.
E.
Statements (All nucleophiles ring open epoxides with
backside attack), (Ring opening of epoxides always follows an
SN2 mechanism), and (Nucleophilic attack always occurs at
the less substituted carbon atom) are all true.
26. Determine the product in the reaction below.
21. Give the IUPAC name for the following compound.
27. Determine the major product in the reaction below.
22. Which of the following compounds has the highest boiling
point?
2
28. What is the product?
36. A secondary alkyl halide reacts with a strong bulky base. The
reaction will proceed via which of the following
mechanism(s)?
29. What is the product?
A.
B.
C.
D.
E.
SN1
SN2
E1
E2
SN1 and E1
30. What is the likely mechanism of this reaction?
31. Which of the following halides is most reactive in an
elimination reaction having first-order kinetics?
32. Which of the following statements is (are) true about an E2
elimination reaction?
A.
It is fastest with 3 halides.
B.
It exhibits second-order kinetics.
C.
A better leaving group should make a faster reaction.
D.
Both (It is fastest with 3 halides) and (It exhibits
second order kinetics) are true.
E.
Statements (It is fastest with 3 halides), (It exhibits
second order kinetics), and (A better leaving group should
make a faster reaction) are all true.
33. Which of the labeled protons in compound A is most readily
abstracted under conditions of E2 elimination?
34. Consider the following exothermic E2 reaction. What rate
equation would be observed for this reaction?
A.
rate = k[CH3CH2CH2I]
B.
rate = k[CH3CH2CH2I][K+ -OC(CH3)3]
C.
rate = k[CH3CH2CH2I][K+ -OC(CH3)3]2
D.
rate = k[CH3CH2CH2I]2[K+ -OC(CH3)3]
E.
There is not enough information given to determine
the rate equation.
35. A tertiary alkyl halide reacts with a strong base. The reaction
will proceed via which of the following mechanism(s)?
A.
B.
C.
D.
E.
SN1
SN2
E1
E2
SN1 and E1
3
CH221 QUIZ 2
ANSWER GRID
Write in each box the answer you think corresponds to the correct answer to that question.
Name……………………………………………..
Student Number…………………….……………
1
2
3
D
C
B
4
5
6
7
8
B
9
10
C
C
11
4-methylcyclohexene oxide
1,2-epoxy-4methylcyclohexane
12
13
14
15
19
20
ZnCl2, HCl
Or SOCl2, pyridine
16
17
18
a>c>b
21
(E)-4-ethyl-2,5dimethyl-3octene
22
23
24
25
B
C
B
A
26
27
28
29
30
SN2
31
C
32
33
E
D
34
35
B
36
D
D
Total score
4