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CHE391H1F 2018 ORGANICCHEMISTRYANDBIOCHEMISTRY E.pdf
CHE391H1F_2018_ORGANICCHEMISTRYANDBIOCHEMISTRY_E.pdf
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CHE391H1F_2018_ORGANICCHEMISTRYANDBIOCHEMISTRY_E.pdf-UNIVERSITY OF TORONTO FACULTY OF APPLIED
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CHE391H1F_2018_ORGANICCHEMISTRYANDBIOCHEMISTRY_E.pdf-UNIVERSITY OF TORONTO FACULTY OF APPLIED
Page 1
UNIVERSITY OF TORONTO
FACULTY OF APPLIED SCIENCE AND ENGINEERING
/
FINAL EXAMINATION, December 12, 2018
DURATION: 2 and
1/2
hrs.
CH
391 H 1 F
-
Organic Chemistry and Biochemistry
Calculator Type: 2
Exam Type: B
Examiner
-
P. Yaneff
Full Name (as registered in ACORN):
Student Number:
Instructions:
Ensure your copy of the exam has all 10 pages, page numbers indicated on the bottom of each page.
Marks for each question and section are indicated. There are four parts to the exam. Answer all questions in
your exam booklet.
Part 1:
Multiple Choice
20
Part 2:
Structure and Nomenclature
10
Part 3:
Reactions and Mechanisms
45
Part
4: General Questions
45
Total
120
Page 2
Part 1: (20 Marks) Multiple Choice (One question has more than one answer)
Consider the
SO
reaction of tert-butyl chloride with iodide ion:
(CH3)3C
-
Cl
+
1
0
3W (CH
3
)
3
C—I
+
CI
O
If the concentration of iodide ion is doubled, the rate of forming tert-butyl iodide will:
(hint: consider mechanism, i.e. how is the product formed?)
(A) Double.
(B) Increase 4 times.
(C) Remain the same.
(D) Decrease.
(B) None of the above.
The relationship between the following two structures is:
(A) enantiomers
(D) identical
CH
3
H OH
H t
OH
CH
3
(B) diastereomers
(E) none of the above
CH
3
HO H
H OH
CH
3
(C) structural isomers
Which of the following alkyl halides would undergo
SN2
reaction most rapidly?
(A) C1-FCH
2
-Br
(B) CH
3
CH
2
- Cl
(C) CH3CH
2
-I
(D) CH
3
CH
2
-F
(B) they react at the same rate
4. Which of the following alkyl halides would you expect to more likely undergo SN 1 reactions?
Cl-I3
CH
3
CH
2
CH
2
CH
2
CH
2
-Br CH
3
CH
2
CH
2
CH—Br CH
3
CH
2
C—Br
CF!
3
CH
3
(A)
(B)
(C)
They will not undergo S
1 reaction
They react at the same rate
S. Which of the following compounds is achiral?
5-Bromodecane
Propanoic acid, CH
3
CH
2
COOH
Lactic acid, CH
3
C(OH)HCOOH
2-M ethyl- 1 -butanol
2
Page 3
6. What is the reagent needed to carry out the following reaction?
CH
3
COOH
I
I
I
L
i
c
T
NO
2
NO
2
ZnIHCI
H
2
Cr0
4
HNO
3
/H
2
SO
4
02
7.
Which of the following alkyl halides would you expect to give the highest yield of substitution
product (SN2) with CH
3
CH
2
0 Na?
CH
3
CH
3
CH
2
CH
2
CJ-l
2
CH
2
-Br
CH
3
CH
2
CH
2
CH— Br
CH
3
CH
2
C—Br
CH
3
CH
3
(A)
(B)
(C)
They
will give same yield of substitution products
None of them gives substitution products
8. Predict which of the following carbocations has the highest energy (least stable):
CH
2
CH
3
CH
3
CH
3
13
6
13
1,
13G
(A)
(B)
(C)
(1))
(E) All are equally stab
le
9.
Bromination of alkanes is a much slower reaction than chlorination. Which of the following is
expected to be the major organic product when 2-methylbutane is allowed to react with Br
2
in the
presence of light or heat?
CH
3
CH3CH2CHCH3
+
Br2 light
CH
3
CH
3
CH
2
CHCH
2
Br
(A)
CH
3
CH
3
CH
2
CCH
3
Br
(B)
CH
3
CHCHCH
3
Br
(C)
CH
3
BrC H
2
CH
2
CHCH
3
(D)
ii
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