CHM2210 Practice Exam 3
This practice exam is intended to demonstrate the types of questions to be expected on
the online Canvas Exam 3. This exam should take you no more than 80 mins.
1. What is the IUPAC name for this compound?
Multiple choice
5
a 7
y
(3R,5R)-3-bromo-5-ethylhept-6-yne
(3R,5R)-5-bromo-3-ethyl-hept-1-yne
(3S,5S)-3-bromo-5-ethylhept-6-yne
(3R,5R)-3-ethyne-5-bromeheptane
2. What is the IUPAC name for this compound?
ii
Multiple choice
6 memylcyclonon
1-methylcyclonon-5-yne
x
(R)-1-methylcyclonon-5-yne
6-methylcyclonon-1-yne
(S) 6-methylcyclonon-1-yne
i
ym
3. Select the line-angle formula that represents 2,5,5-trimethylhept-1-en-3-yne.
0
I
4. Select the structure that represents (R)-4-ethylcyclooct-1-yne.
a
5. Rank the following radicals in terms of their stability (least stable to most stable).
Fill in multiple blanks
least stable B
__ < __
C
A < __
most stable
6. Rank the C–H bonds indicated below in terms of their bond dissociation enthalpy (BDE).
Fill in multiple blanks.
CI CI
Lowest C
__ < __ < B
A __ Highest
7. Choose the expected product of the reaction sequence below
T
HN
s
ii
fit Ii
8. How many equivalents of NaNH2 are required for the first step of this reaction?
Numerical Answer:
J
f
a'timpani
HD H
9
3
O
9. Which C–H bond below is weaker (in terms of bond strength), A or B?
Pull down menu selection: A or B
10. Consider the reaction shown below. Complete the two propagation steps by predicting the
structures of A–C.
Pull down menu selections:
Select compound A from List 1. (Answers: 1a, 1b, 1c, 1d)
Select compound B from List 2. (Answers: 2a, 2b, 2c, 2d)
Select compound C from List 2. (Answers: 2a, 2b, 2c, 2d)
11. Select a reasonable reaction intermediate to the following reaction
12. Select the expected products for each of the following reactions.
12a.)
12b)
12c)
12d)
13. How many different monochlorination products may be formed in the reaction below?
Ignore stereochemistry.
Numerical answer:
14. Select the expected products for the following reactions.
15. Propose a synthesis for the target molecules shown below. You must start your synthetic
route using the compounds shown; from there, you can use any other materials/reagents
you need. Use the pull-down menus to select the reagents/conditions. You must select one
option for each of the pull-down menus below.
List of Reagents/Conditions (Dropdown menu):
Br2, CH2Cl2
O3
Br2, H2O
(CH3)2S
NaNH2, NH3
HCC- Na+ (sodium acetylide)
H2O
BH3, THF
H2, Lindlar
NaOH, H2O2
Na, NH3
Hg(OAc) 2, THF/H2O
H2, Pd
NaBH4, H2O
HgSO4, H2SO4, H2O
CH3Br
HB(sia)2, THF
CH3CH2Br
OsO4, H2O2, H2O
H2O, H2SO4 (cat.)
Synthesis 1 (4 steps):
Synthesis 2 (3 steps):
CHM2210 Practice Exam 3
This exam should take no more than 80 mins.
1. What is the IUPAC name for this compound?
Multiple choice
(3R,5R)-3-bromo-5-ethylhept-6-yne
(3R,5R)-5-bromo-3-ethyl-hept-1-yne
(3S,5S)-3-bromo-5-ethylhept-6-yne
(3R,5R)-3-ethyne-5-bromeheptane
2. What is the IUPAC name for this compound?
1-methylcyclonon-5-yne
(R)-1-methylcyclonon-5-yne
6-methylcyclonon-1-yne
(S) 6-methylcyclonon-1-yne
Multiple choice
3. Select the line-angle formula that represents 2,5,5-trimethylhept-1-en-3-yne.
Multiple choice, Answer: 2
4. Select the structure that represents (R)-4-ethylcyclooct-1-yne.
Multiple choice, Answer: 2
5. Rank the following radicals in terms of their stability (least stable to most stable).
Fill in multiple blanks
least stable __ < __ < __
most stable
least stable B < A < C most stable
6. Rank the C–H bonds indicated below in terms of their bond dissociation enthalpy (BDE).
Fill in multiple blanks.
Lowest __ < __ < __
Lowest
C<A<B
highest BDE
7. Choose the expected product of the reaction sequence below
Multiple choice, Answer: 4
8. How many equivalents of NaNH2 are required for the first step of this reaction?
Numerical answer: 3
9. Which C–H bond below is weaker (in terms of bond strength), A or B?
Pull down menu selection: A or B
10. Consider the reaction shown below. Complete the two propagation steps by predicting the
structures of A–C.
Pull down menu selections:
Select compound A from List 1. (Answers: 1a, 1b, 1c, 1d)
Select compound B from List 2. (Answers: 2a, 2b, 2c, 2d)
Select compound C from List 2. (Answers: 2a, 2b, 2c, 2d)
11. Select a reasonable reaction intermediate to the following reaction
Multiple choice
Answer: 1
12. Select the expected products for each of the following reactions.
Pull down menu
Select A from the compounds shown above. Answer: 3
Select B from the compounds shown above. Answer: 2
Pull down menu
Select A from the compounds shown above. Answer: 1
Select B from the compounds shown above. Answer: 4
Pull down menu
Select A from the compounds shown above. Answer: 3
Select B from the compounds shown above. Answer: 1
Pull down menu
Select A from the compounds shown above. Answer: 2
Select B from the compounds shown above. Answer: 4
13. How many different monochlorination products may be formed in the reaction below?
Ignore stereochemistry.
Numerical answer: 3.
14. Select the expected products for the following reactions.
Pull down menu
Select A from the compounds shown above. Answer: 1
Select B from the compounds shown above. Answer: 2
15. Propose a synthesis for the of the target molecules shown below. You must start your
synthetic route using the compounds shown; from there, you can use any other
materials/reagents you need. Use the pull-down menus to select the reagents/conditions.
You must select one option for each of the pull-down menus below.
TWO SEPARATE SYNTHESIS PROBLEMS.
List of Options (Dropdown menu):
Br2, CH2Cl2
O3
Br2, H2O
(CH3)2S
NaNH2, NH3
HCC- Na+ (sodium acetylide)
H2O
BH3, THF
H2, Lindlar
NaOH, H2O2
Na, NH3
Hg(OAc) 2, THF/H2O
H2, Pd
NaBH4, H2O
HgSO4, H2SO4, H2O
CH3Br
HB(sia)2, THF
CH3CH2Br
OsO4, H2O2, H2O
H2O, H2SO4 (cat.)
Synthesis 1:
4 Pull-downs:
Step a: Br2, CH2Cl2
Step b: NaNH2, NH3
Step c: CH3Br
Step d: H2, Pd
Synthesis 2:
3 Pull-downs:
Step a: Br2, CH2Cl2
Step b: NaNH2, NH3
Step c: CH3CH2Br