Fa24 mock CM2213 exam 2 BLANK

Polytechnic Tutoring Center
NYU Tandon School of Engineering

CM-UY 2213
Mock Exam 2
November 9 2024
11:00 AM - 12:00 PM and 1:30 - 2:30 PM
● This exam is for practice, only. It was made by tutors at the PTC. It is not representative of your
real exam given by the department.
● The second exam covers chapters 4 through 7 in the textbook

● Use the space provided to you on these pages to reach your answers
● You may use a model kit
● Try to closely simulate a real exam environment
○ Do not use your phone until the exam is finished
○ Do not leave the room until the exam is finished
● You have 60 minutes to complete this exam, and the number of questions is meant to simulate
what may be expected of you in an 60-minute exam
● After 60 minutes, we will spend 60 minutes to review the correct answers
● There is no answer key
○ But if there were an answer key, each question would be worth the same amount of
points
● Bring your questions to the PTC tutors on floor 9 of 2MTC if any of the following apply:
○ You have questions that were not answered during the review session
○ You are not taking this exam at one of the in-person review sessions but you have
questions about the exam
○ You have questions about course topics
CM-UY 2213 PTC Mock Exam 2
11/9/24
Isopulegol is isolated from the essential oil of European pennyroyal. The line structure of isopulegol is
given below:
isopulegol
1. How many stereocenters are present in isopulegol? __
2. How many stereoisomers are possible for isopulegol? __
Consider (-)-isopulegol, also named (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol.
3. Draw the line structure of (-)-isopulegol.
4. How many stereoisomers of (-)-isopulegol are diastereomers of (-)-isopulegol? Draw the line
structure of one diastereomer.
5. Draw the chair conformations of (-)-isopulegol. Observe the given numbering.
lowest energy chair conformation highest energy chair conformation
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11/9/24
Copy the line structure of (-)-isopulegol from problem 3:
6. Which of the following must be dextrorotatory? Circle all that apply.
I II III IV
Consider the line structure below:
7. Draw the chair conformation of a stereoisomer of the above structure with the greatest number
of diaxial interactions between methyl groups. Observe the given numbering.
8. What is the complete name of the compound you drew above?
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11/9/24
Consider the following compounds:

1 2 3 4 5 6
H2O tertbutylchloride NaSCH3 ethanol chloroethene
7 8 9 10 11 12
1-iodo- 1-bromo-
2-propanol NaOH
2-propene 3-butene
9. For the compounds above, perform the below:

● If the formula or line structure is given, write the complete name below the formula or
line structure
○ Skip compounds 3 and 11
● If the name is given, draw the line structure below the name
10. Using the numbers 1-12, sort the compounds above into the categories below. Note that some
compounds may belong to more than one category.
This is not likely to be an explicit question that you will see on the real exam, but you must
know how to do this in order to succeed. Practice.
poor nucleophiles good nucleophiles SN1 electrophiles SN2 electrophiles
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The compounds from the previous page are copied below:

1 2 3 4 5 6
H2O tertbutylchloride NaSCH3 ethanol chloroethene
7 8 9 10 11 12
1-iodo- 1-bromo-
2-propanol NaOH
2-propene 3-butene
11. If the carbon chain connecting the halide and the arene in compound 11 were one carbon
shorter or longer, would it perform the same substitution reaction(s)? Explain your answer.
12. Draw a complete mechanism for the reaction of compound 3 with compound 4 in a polar
aprotic solvent. If multiple pathways are possible, draw them all.
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11/9/24
13. Draw a complete mechanism for the reaction of compound 8 with compound 9 when heated. If
multiple pathways are possible, draw them all.
14. Draw a complete mechanism for the reaction of CH2CN1- with an isomer of C4H6 that has a
proton with a pKa value of 25. Label the acid, base, conjugate acid, and conjugate base. If there
is not an equilibrium, state in which direction the reaction proceeds. If there is an equilibrium,
indicate which side is favored.
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11/9/24
Dehydroabietic acid, which has been investigated for its antiviral properties, can be synthesized in a
series of reactions from abietic acid, which is found in the rosin of coniferous trees.
abietic acid dehydroabietic acid
15. Which of the following do the above compounds have in common? Circle all that apply.
I. bridged tricyclic ring
II. meso compound
III. four stereocenters
IV. equatorial carboxylic acid
V. an isomer with an arene and three 𝜋 bonds
16. Which of the following is true? Circle all that apply.

I. both compounds have a resonance form with a tertiary carbanion
II. the conversion of abietic acid to dehydroabietic acid inverts a stereocenter
III. the compounds both contain 3 vinyl hydrogen atoms
IV. four consecutive 2p orbitals are conjugated in abietic acid
V. (R) configuration at the stereocenter closest to the carboxylic acid for both compounds
17. Which of the following compounds is an isomer of abietic acid? Circle all that apply.
I II III IV V
18. Which of the above compounds has a proton with a pKa value of 41? Circle all that apply.
I II III IV V
19. Which of the above compounds is achiral but not meso? Circle all that apply.
I II III IV V
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11/9/24
20.What are the names of the compounds below? Circle the lower energy compound. Circle one
answer that correctly identifies their relationship. Hint: consider the chairs.
Name: Name:
conformations enantiomers diastereomers regioisomers
21. Draw the line structure of bicyclo[4.2.1]nonane.

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Polytechnic Tutoring Center

NYU Tandon School of Engineering

● The second exam covers chapters 4 through 7 in the textbook

1. How many stereocenters are present in isopulegol? __

2. How many stereoisomers are possible for isopulegol? __

Consider (-)-isopulegol, also named (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol.

3. Draw the line structure of (-)-isopulegol.

5. Draw the chair conformations of (-)-isopulegol. Observe the given numbering.

lowest energy chair conformation highest energy chair conformation

Copy the line structure of (-)-isopulegol from problem 3:

6. Which of the following must be dextrorotatory? Circle all that apply.

Consider the line structure below:

8. What is the complete name of the compound you drew above?

Consider the following compounds:

H2O tertbutylchloride NaSCH3 ethanol chloroethene

9. For the compounds above, perform the below:

poor nucleophiles good nucleophiles SN1 electrophiles SN2 electrophiles

The compounds from the previous page are copied below:

H2O tertbutylchloride NaSCH3 ethanol chloroethene

abietic acid dehydroabietic acid

16. Which of the following is true? Circle all that apply.

conformations enantiomers diastereomers regioisomers

21. Draw the line structure of bicyclo[4.2.1]nonane.

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