CHM3120 - Midterm exam 2
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CHM 3120
–
Intermediate Organic Chemistry
1
Midterm Exam #2: 8:30
–
9:50, Nov 11, 2022.
Student name:
Student number:
Signature:
Note
: The marking scheme is given for each question as a guide. It is subject to minor changes.
The use of molecular models is permitted. No other resources besides a pen and paper are permitted.
This exam is 7 pages long. The back of each page can be used for extra space.
1.
Illustrate the products or missing reactants for the following reactions. If multiple products
are possible, draw only the major product (2 mark each)
CHM 3120
–
Intermediate Organic Chemistry
2
2.
Consider the following multi-step synthetic sequence
CHM 3120
–
Intermediate Organic Chemistry
3
a)
Propose a mechanism
EITHER
for the synthesis of
B
from
A
OR
F
from
E
. (6 marks)
b)
Propose structures for
C
and
D
. Explain the regiochemistry (6 marks)
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CHM 3120
–
Intermediate Organic Chemistry
4
c)
Provide a complete chemical equation for the reaction of a brominated heterocycle (e.g. pyrrole
D
) with
n
BuLi. Which side of the equilibrium is favoured? Why? (3 marks)
3.
a) Propose structure for the products that may form under the indicated conditions. Explain
your answers. (6 marks)
CHM 3120
–
Intermediate Organic Chemistry
5
b) Predict which of the following reactions will be occur with the fastest rate. Explain your answer. (2
marks)
c) The following pairs of reagents can react via [4+2] cycloaddition. Predict which reaction will occur
with the fastest rate. Explain your answer. (2 marks)
CHM 3120
–
Intermediate Organic Chemistry
6
4.
Consider the following [4+2] cycloaddition reaction.
a)
Use frontier molecular orbital (FMO) theory to explain why thermal [4+2] cycloaddition
reactions such as this one are feasible but most [2+2] cycloaddition reactions are not. (4 marks)
b)
Use FMO theory to explain why the illustrated regioisomer is favoured. (2 marks)
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CHM 3120
–
Intermediate Organic Chemistry
7
c)
Predict the stereochemistry of the major product at the three labelled stereocenters. Justify
your answer. (4 marks)
5.
BONUS: Propose a mechanism for the following reaction that exploits the fact that pericyclic
reactions are reversible. (4 marks)
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OH
I
C
||
O
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1
O PRINCIPLES OF ORGANIC CHEMISTRY
Classifying organic reactions
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2
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Check
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D) 1,4,7-trimethylheptane
E) decane
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