CHM1321 C QUIZ A 2019 Page 1 of 4

LAST NAME: ____________________________________ FIRST NAME: ___________________________

February 15th 2019 STUDENT NUMBER: _____________________

CHM 1321 C QUIZ TIME ALLOWED: 30 min

There are 5 pages in this quiz. A periodic table is provided at the end. You may GENTLY
remove this page and use it to cover your work. Any scratch work should be done on this
page. You may keep this page afterwards if you wish. Molecular model kits (in a clear plastic
bag or container) are allowed. You may answer in pen or pencil, and may use different
colours.

1. (2 pts) Name the functional groups in the following molecules.

O
N
OH
H O

2. (2 pts) The following molecule is the water-soluble form of Valium. Add lone pairs where
necessary to the following structure to create full octets on all the appropriate atoms.
Then add formal charges, where necessary. Finally, state the hybridization and geometry
of the indicated atoms.

H
N Cl

N
O

3. (1 pt) From the list below, circle the strongest intermolecular force found in iso-propanol.

DIPOLE–DIPOLE HYDROGEN–BONDING ION-DIPOLE

DIPOLE–INDUCED DIPOLE INDUCED DIPOLE–INDUCED DIPOLE

CHM1321 C QUIZ A 2019 Page 2 of 4

4. (4 pts) In the following table, provide the missing IUPAC name or line structure. Clearly
show correct geometry, where necessary.

Name Structure

Cl

3,3-dimethyl-oct-6-ynal

5. (3 pts) Clearly draw the two chair conformers of cis-2-ethoxy-cyclohexanol and label the
more stable conformer.

6. (3 pts) Draw the line structures both enantiomers of 3-bromo-1-butyne. Label the R and S
isomer.
CHM1321 C QUIZ A 2019 Page 3 of 4

7. (3 pts) Consider the various conformers of following molecule along the indicated bond
(the eye shows the desired perspective). Draw and label Newman projections for the
HIGHEST and LOWEST energy conformers of this molecule.

Cl
OH

8. (5 pts) Draw CHCF using the LCAO (hybridization) method. Label all the orbitals (p, sp,
sp2, or sp3) and the bonds (σ or π). Include a legend if you’re using different colours.

FINAL QUIZ SCORE: ________ / 23

CHM1321 C Midterm 1 2019 Page 1 of 11

LAST NAME:

FIRST NAME:

Student number:

CHM1321 C: ORGANIC CHEMISTRY I

MIDTERM 1 - 2019

Time allowed: 90 minutes

There are 11 pages in this test. A periodic table and a pKa table are provided at the end. You may

GENTLY remove them and use them as scrap paper and/or to cover your work. You may keep these

pages afterwards if you wish.

Molecular model kits (in a clear plastic bag or container) and non-programmable calculators are

allowed. Stencils must be pre-approved by the professor before use. You may answer in pen or

pencil, and may use different colours.

Please show all work to receive part marks.

Cellular phones, unauthorized electronic devices and course notes are not allowed during this exam.
Phones and devices must be turned off and put away in your bag. Do not keep them in your
possession, such as in your pockets. If caught with such a device or document, the following may
occur: academic fraud allegations will be filed which may result in you obtaining a 0 (zero) for the
exam.

By signing below, you acknowledge that you have read and ensured that you are complying with the
above statement.

Signature:________________________________
CHM1321 C Midterm 1 2019 Page 2 of 11

Part A B C Bonus Total

Points 10 20 20 3 50

Mark

TA

Part A

1. (2.5 pts) Draw the full Lewis structure of CH3ONa. Indicate clearly which bonds are ionic,
non-polar covalent, or polar covalent.

2. (3 pts) Give the line structure or the IUPAC names for the following compounds:

STRUCTURE NAME
HO

para-chlorophenol
CHM1321 C Midterm 1 2019 Page 3 of 11

3. (0.5 pt) A Lewis Acid can either act as a Brønsted Acid or as a nucleophile.

TRUE FALSE

4. (0.5 pt) Which of the following Newman projections represents 2-methylhexane?

CH 3 CH(CH 3)2 CH 3 H
H H H 3C H H H H CH2CH 3

H CH 3 H H H 3C H H H
CH2CH2CH 3 CH2CH 3 CH2CH 3 CH 3

A B C D

5. (0.5 pt) You purchase a bottle of Advil (ibuprofen) from Shoppers Drug Mart and test the
optical purity of the product. The sample shows an optical rotation of +23.2º. If the
specific rotation of pure S-ibuprofen is +54.5º, what is the optical purity of Advil?
£ Advil is made of pure R-ibuprofen.
£ Advil is made of pure S-ibuprofen.
£ Advil is a mixture of 42.5% R-ibuprofen and 57.5% S-ibuprofen.
£ Advil is a mixture of 57.5% R-ibuprofen and 42.5% S-ibuprofen.

6. (1.5 pts) Using the electron-pushing arrows as a guide, draw the expected product(s) of
the following reaction.

H
O O

O N

7. (1.5 pts) Add lone pairs and electron-pushing arrows as needed to complete the
following reaction:

H H
H H H H
O
+ N
N O
H H H H
H H
CHM1321 C Midterm 1 2019 Page 4 of 11

Part B

8. Consider the various conformers of following molecule along the indicated bond (the eye
shows the desired perspective).
H Br
H F
H 3C F
a. (4 pts) On the following axes, sketch the potential energy diagram (as accurately as
possible) as the FRONT ATOM is rotated CLOCKWISE.
Potential Energy

0º 60º 120º 180º 240º 300º 360º

Dihedral Angle

b. (3 pts) Draw the Newman projections for the highest and lowest energy conformers of
this molecule. Label your conformers with the appropriate name from this list: gauche-
staggered; anti-staggered, partially eclipsed; fully eclipsed.
CHM1321 C Midterm 1 2019 Page 5 of 11

9. Aspartic acid (shown at right) is dissolved in a solution at a pH = 7.0. O NH2

OH
HO
a. (0.5 pt) The absolute stereochemistry of the chiral centre in
O
aspartic acid is: R S aspartic acid

b. (0.5 pt) Which of the following will be the major form of aspartic acid at pH = 7.0?

O NH2 O NH3 O NH2 O NH3

OH OH O O
HO HO O O
O O O O

A B C D
c. (2 pts) In the space below, explain your choice.

10. (2 pts) Below is the structure of lysergic acid diethylamide, more commonly known as
LSD. On the right, clearly draw a diastereoisomer of this molecule.

CH 3
H
N
N H
O

N
CHM1321 C Midterm 1 2019 Page 6 of 11

11. (2 pts) A student is monitoring the reaction below using TLC. On the templates provided,
draw and label a picture of the TLC plate…

O HO OH

+ H 2O

A B

A B A B
CO-SPOT CO-SPOT

a. … after 50% completion. b. … at the end of the reaction.

12. (6 pts) Draw the other possible resonance structures of the ion below, using electron-
pushing arrows to show the conversion between resonance forms. Label the most stable
resonance form, and then draw the resonance hybrid.

OH
H 3C
CHM1321 C Midterm 1 2019 Page 7 of 11

Part C

13. (4 pts) Clearly indicate the specific relationship (structural isomers, conformers,
enantiomers, diastereoisomers, etc.) between molecule A and structures B through E.

OH OH
OH
OH OH
A B C D E

A and B are: A and C are:

A and D are: A and E are:

14. For the acid-base reaction below:

H
P S
+

a. (2 pts) Draw a mechanism and the expected products.

b. (2 pts) Does the equilibrium favour the starting materials or products? Justify your
answer.
CHM1321 C Midterm 1 2019 Page 8 of 11

15. (6 pts) Using an MO energy level diagram, show and explain why “F22–” does not exist.
Label all parts of your diagram.
CHM1321 C Midterm 1 2019 Page 9 of 11

16. (6 pts) Draw the full Lewis structure of BCl3, including lone pairs. What is the hybridization
and geometry of the central atom? What is the overall molecular geometry? What is the
approximate Cl-B-Cl bond angle? Add dipole moment arrows for the bonds in BCl3. Is
this molecule polar or non-polar?

BONUS – 3 pts

The molecule at right is called 5-hydroxy-1,3-dioxane, and it is an exception to a rule OH

we learned in class: this molecule is more stable with the OH group in the axial
position rather than in the equatorial position. Give a possible explanation why, and O O
support your answer with a chair conformer.
CHM1321 C Midterm 2 2019 Page 1 of 13

LAST NAM E:

FIRST NAM E:

Student num ber:

CHM1321 C: ORGANIC CHEMISTRY I

MIDTERM 2 - 2019

Time allowed: 90 minutes

There are 13 pages in this test. A periodic table, pKa table, and SCRAP PAGE are provided at the

end. You may GENTLY remove them and use them as scrap paper and/or to cover your work. You

may keep these pages afterwards if you wish.

Molecular model kits (in a clear plastic bag or container) and non-programmable calculators are

allowed. Stencils must be pre-approved by the professor or TA before use. You may answer in pen or

pencil, and may use different colours.

Please show all work to receive part marks.

Cellular phones, unauthorized electronic devices and course notes are not allowed during this exam.
Phones and devices must be turned off and put away in your bag. Do not keep them in your
possession, such as in your pockets. If caught with such a device or document, the following may
occur: academic fraud allegations will be filed which may result in you obtaining a 0 (zero) for the
exam.

By signing below, you acknowledge that you have read and ensured that you are complying with the
above statement.

Signature:________________________________
CHM1321 C Midterm 2 2019 Page 2 of 13

Part A B C Bonus Total

Points 10 20 20 3 50 (+3)

Mark

TA

Part A

1. (2 pts) Identify the functional group in the following molecules:

CH3
OH HO H
O O

O N H H
CN

2. (3 pts) On the following template, draw the π and π* molecular orbitals for the C=O bond.
Then, show the mechanism and product(s) obtained when this compound reacts with a
nucleophile (Nu).

H 3C
C O
H
CHM1321 C Midterm 2 2019 Page 3 of 13

3. (0.5 pt) In an acid-catalyzed nucleophilic addition reaction the role of the acid is to activate
the nucleophile.
TRUE FALSE

4. (0.5 pt) The awesome German word used to indicate a switch in polarity at a carbon atom

(from positive to negative, or visa versa) is ________________________.

5. (0.5 pt) Organopotassium reagents are not used as nucleophiles in organic synthesis

because ________________________________________________________________________.

6. (3 pts) On the axes provided at right,

draw a line (or curve) representing the
reaction profile for a reaction A à C ENERGY
with the following characteristics:
• a two-step mechanism, A à B, then
BàC
• Ea of step 2 = 50 kJ/mol
• step 2 is two times slower than step 1
• ∆H = –80 kJ/mol

On your profile, label the following: A, B,

C, Ea1 (for step 1), Ea2 (for step 2), and
∆H. REACTION PROGRESS

7. (0.5 pt) Circle the polar aprotic solvent(s) and underline the polar protic solvents:

O OH
CH 3OH H 2O
CHM1321 C Midterm 2 2019 Page 4 of 13

Part B
8. (1 pt) Add lone pairs and electron-pushing arrows as needed to complete the following
reaction step:
O O
+ X
X

(1 pt) In organic chemistry, “X” is called a _______________________________________.

(1 pt) For which of the following possible X substituents would you expect the above step
to take place? Circle all that apply.

H2O NH3 NH2 OCH3 CH3 H Br Cl OH

9. (3 pts) Draw the full mechanism and show the final product of the following transformation.
Clearly show stereochemistry (if necessary).
Br O
Br
H 1) 2 equivalents of LiC CCH 3/ether
?
2) H 3O+ /H2O
H H
HO
CHM1321 C Midterm 2 2019 Page 5 of 13

10. (6 pts) Draw a mechanism for the following acid-catalyzed reaction.

O HCl O O
HO OH
CHM1321 C Midterm 2 2019 Page 6 of 13

11. (3 pts) Draw the structures of the compounds A to C below (major organic product only).

LiAlH4/ether H3O+/H2O CH2O/HA

C7H12O2 B C
–H2O O O
A

A B C

12. The reaction below shows an incorrect final product.

a. (2 pts) Why is this the wrong product? Explain in one or two sentences.
b. (3 pts) Draw the mechanism for the reaction, showing the formation of the correct final
product.
O OH
1) CH 3C CLi (1 equivalent)/ether
2)H3O+ /H2O
N N
O O

CH 3
CHM1321 C Midterm 2 2019 Page 7 of 13

Part C
13. (6 pts) For each of the following, provide the missing product or reagents (no
mechanisms). Clearly show stereochemistry where necessary.

CH3 HCl
O + N
a) OH

HBr
N + H 2O
b)

1) NaBH 4
Br
2) H 3O+ /H2O
H
H
O
c)

14. (2 pts) One of the following statements is false. Select the incorrect statement, and then in
the space below, provide a corrected version.
£ Reduction with lithium aluminum hydride requires a polar aprotic solvent.
£ Addition of a catalyst accelerates both the forward and reverse directions of a reaction.
£ In an acid-catalyzed acetal formation reaction, water must be removed in order for the
reaction to proceed towards products.
£ For safety reasons, in the lab, cyanohydrins are generally formed under acidic
conditions.
CHM1321 C Midterm 2 2019 Page 8 of 13

15. (3 pts) Provide a possible retrosynthesis for the following, starting from bromobenzene.

16. (4 pts) When cyclohexanone is treated with H2O, an equilibrium is established between
cyclohexanone and its hydrate. This equilibrium greatly favours the ketone, and only trace
amounts of the hydrate can be detected. In contrast, when cyclopropanone is treated with
H2O, the resulting hydrate predominates at equilibrium.
a. Draw both transformations (show the reactant(s) and product(s)).
b. Can you suggest an explanation for the curious observation described above?
CHM1321 C Midterm 2 2019 Page 9 of 13

17. (5 pts) The reagent below is diisobutylaluminum hydride, or DIBAL. Like sodium
borohydride, it is a source of nucleophilic hydride. For the following reaction, (with
appropriate work-up) draw both possible products of the reaction; indicate the major
product and provide a justification for your choice. Assign configurations (R or S) to all
stereocentres in the products. Unlike NaBH4, reductions performed with DIBAL require
equimolar amounts of DIBAL and substrate. Can you explain this difference?

Al + O
H
DIBAL
CHM1321 C Midterm 2 2019 Page 10 of 13

BONUS (+3 pts)

Draw a mechanism to explain the following transformation.

CH3
H3O+ O H H
O N N
CH3 +
H 2O HO H 3C CH3
CHM1321C Final Exam 2019 Page 1 of 16

LAST NAME: FIRST NAME:

Student number: Seat Number:

CHM1321 C: ORGANIC CHEMISTRY I

FINAL EXAM – APRIL 2019

Professor: K.-S. Focsaneanu (Fox) Time allowed: 3 hours

Part A B C Bonus Total

Points 20 40 40 +3 100 (+ 3)

M ark

TA

There are 16 pages in this exam. A periodic table and pKa table are provided at the end. You may
GENTLY remove these pages and use them to cover your work. Any scratch work should be done on
these pages or on the supplied scrap paper. You may keep them afterwards if you wish.

Molecular model kits (in a clear plastic bag or container) are allowed. Faculty-approved calculators
are allowed. You may answer in pen or pencil, and may use different colours.

Cellular phones, unauthorized electronic devices or course notes (unless an open-book exam) are not
allowed during this exam. Phones and devices must be turned off and put away in your bag. Do not
keep them in your possession, such as in your pockets. If caught with such a device or document, the
following may occur: academic fraud allegations may be filed which may result in your obtaining a 0
(zero) for the exam.

By signing below, you acknowledge that you have read and ensured that you are complying with the
above statement.

Signature:________________________________

Good luck on this exam and in your future studies!

CHM1321C Final Exam 2019 Page 2 of 16

Part A
1. (0.5 pt) In cycloalkanes, ring strain increases with increasing number of atoms in the ring.

TRUE FALSE

2. (2 pts) The molecule shown below is known as Pepcid, a drug used to reduce gastric acid
production. State the hybridization and atomic geometry of the indicated atoms.

NH 2 NH 2
O
H 2N N
S N S NH 2
N
S O

3. (0.5 pt) In organic chemistry, a molecule is reduced when the number of atoms that are

less electronegative than carbon ______________________________________________.

4. (1 pt) Among the line structures shown, which corresponds to the correct product of the
reaction shown?

Cl2 Cl Cl
Cl Cl
Cl Cl Cl Cl

CH 3
5. (1 pt) Complete the diagram at right so that it represents
(S)-2-butanol. OH

6. For the following reaction:

H O H

O H
Li + O Li
H 2O

a. (2 pts) Add electron-pushing arrows to the scheme above.

b. (2 pts) Draw and name the final product.
c. (1 pt) What is the thermodynamic driving force for the reaction?
CHM1321C Final Exam 2019 Page 3 of 16

7. (2 pts) Place the following molecules in order of increasing solubility in water.

NH 3 Cl CO2H CO2CH 3 CO2CH 3

8. (3 pts) In the following table, provide the missing IUPAC name or line structure.

Name Structure

OH

5,5,5-trifluoropentanal

9. (2 pts) In the space below, draw an example of an oxonium ion and a halonium ion.

10. (3 pts) A reactant X can undergo two separate reactions to yield either product Y or
product Z. According to following reaction profiles for both processes, which product, Y
or Z, would be in greater abundance at equilibrium? Explain your choice in one or two
sentences.
ENERGY

X
Y

REACTION COORDINATE
CHM1321C Final Exam 2019 Page 4 of 16

Part B

11. (3 pts) Clearly indicate the specific relationship (structural isomers, conformers,
enantiomers, diastereomers, etc.) between the following pairs of molecules.

O O

OH OH OH OH

OH
Cl
Cl OH

OH NH2
H NH2

H CH3
Ph OH

12. (0.5 pt) You purchase a bottle of Advil (ibuprofen) from Shoppers Drug Mart and test the
optical purity of the product. The sample shows an optical rotation of +23.2º. If the
specific rotation of pure S-ibuprofen is +54.5º, what is the optical purity of Advil?
£ Advil is made of pure R-ibuprofen.
£ Advil is made of pure S-ibuprofen.
£ Advil is a mixture of 42.5% R-ibuprofen and 57.5% S-ibuprofen.
£ Advil is a mixture of 57.5% R-ibuprofen and 42.5% S-ibuprofen.

13. (2.5 pts) Draw the expected products of the following reaction (no mechanisms). Label
the major product. Label the products as resulting from either 1,2-addition or 1,4-
addition.

CH 3 HCl/H 2O
CHM1321C Final Exam 2019 Page 5 of 16

14. The following questions all pertain to trans–1,2–dibromocyclohexane.

a. (3 pts) Draw its two chair conformers and label the more stable conformer.
b. (2 pts) When this molecule is dissolved in organic solvents, it is experimentally
observed that the relative amounts of the two chairs depend on the polarity of the
solvent. Can you explain this observation?
c. (1 pt) Which of the two chair conformers would be more favoured in CH2Cl2?

15. (5 pts) Draw CH2CHCH2CHO using the LCAO (hybridization) method. Label all the
orbitals (p, sp, sp2, or sp3) and the bonds (σ or π). Include a legend if you’re using
different colours.
CHM1321C Final Exam 2019 Page 6 of 16

16. (6 pts) Draw a mechanism to explain the following reaction.

O HO
OH H 3O+ /H2O O
O O

17. (4 pts) Provide the structures of the compounds A to D below.

O
O OH
HO Ph H 3O+ /H2O
CH 3Li H 3C
A ether
B ether
C D
H 3O+ /H2O

A B

C D
CHM1321C Final Exam 2019 Page 7 of 16

18. The following is synthesis for the formation of a fragrance from bromobenzene.
a. (2 pts) First, draw the structures of the products of these reactions.

Br Mg

ether
A

mCPBA

b. (3 pts) Now, draw the mechanism for the reaction of A and B together, followed by
aqueous acid workup:

c. (3 pts) How many stereoisomers are possible for the final product? Draw their
structures unambiguously, and label any stereocentres as R or S.
CHM1321C Final Exam 2019 Page 8 of 16

19. (5 pts) Complete the following by providing the missing product or reagents (no
mechanisms). Show stereochemistry, when necessary.

a.
CH3 HCl
O + N
OH

b.

Cl
H 3C
AlCl3

c.
O O
H H
O O

OH
H H
OH

d.

OH

e.

H 3O+ /H2O
C C H
CHM1321C Final Exam 2019 Page 9 of 16

Part C Cl2

N
20. Consider the following reaction: H2O (solvent)

a. (4 pts) Draw a detailed mechanism for the reaction, including all final products.

b. (3 pts) Provide a brief explanation for the regiochemistry of the final product. Support
your answer by drawing a structure or scheme.

c. (2 pts) Briefly account for the stereochemistry of the final product. Support your answer
by drawing a structure or scheme.
CHM1321C Final Exam 2019 Page 10 of 16

21. (8 pts) In the molecule below which proton, Ha or Hb, is more acidic? Justify your answer,
by comparing the relative resonance structures of the two possible conjugate bases.
Which conjugate base is aromatic? In the space below, draw the LCAO orbital diagram of
its π–system.

Ha
Hb

CH3
CHM1321C Final Exam 2019 Page 11 of 16

22. (6 pts) Place the following reagents in the correct order to complete the synthesis below.
Each reagent is used only once.

1) _____ 3) _____ 5) _____

O
2) _____ 4) _____ OH 6) _____ O
OH
O
O
O OH

formaldehyde NaBH4/ethanol
PhMgBr/ether CH3SCH3 O3 with workup H3O+/H2O
with Dean-Stark Trap
A B C D E F

23. (4 pts) In the laboratory, you are asked to separate a mixture of aniline and toluene via
extraction. To a 20 mL solution containing both compounds in dichloromethane (d =
1.33 g/mL), you add 10.0 mL of a solution of 1.0 M HCl in water, and add the mixture to
a separatory funnel. The funnel is shaken gently and left to sit on a support, and the
liquid separates into two phases. Complete the table below, clearly indicating the
identity and the contents of each phase.

The upper layer is: and contains:

ORGANIC

AQUEOUS

(draw all species present)

The bottom layer is: and contains:

ORGANIC

AQUEOUS

(draw all species present)

CHM1321C Final Exam 2019 Page 12 of 16

24. (3 pts) Create a complete retrosynthesis for the following compound, starting from
benzene.
NH2

Br

25. (3 pts) Propose a forward synthesis of the compound below starting from an alkene and
using any other reagents that you require. Make sure that the compound below is the
major product in your synthesis.

H3CO CH3

Br
CHM1321C Final Exam 2019 Page 13 of 16

26. A student performs the following reaction and observes the formation of two products.
Br 2
2 products
FeBr 3
a. (2 pts) What is the function of the FeBr3? Explain, using a sentence and a chemical
reaction.
b. (2 pts) Draw the structures of the two products, and indicate which is the major product
and which is the minor product. Why are they not formed in equal amounts?
c. (3 pts) Why is bromination of tert-butylbenzene kinetically faster than bromination of
plain benzene? Draw reaction intermediates and a reaction energy profile to support
your answer.
CHM1321C Final Exam 2019 Page 14 of 16

Bonus – 3 pts
Draw a mechanism to explain the observed final product.

HCl (trace) OH
OH
H 2O

O
CHM1321 C QUIZ A 2019 Page 1 of 3

LAST NAME: ____________________________________ FIRST NAME: ___________________________

February 15th 2019 STUDENT NUMBER: _____________________

CHM 1321 C QUIZ TIME ALLOWED: 30 min

There are 5 pages in this quiz. A periodic table is provided at the end. You may GENTLY
remove this page and use it to cover your work. Any scratch work should be done on this
page. You may keep this page afterwards if you wish. Molecular model kits (in a clear plastic
bag or container) are allowed. You may answer in pen or pencil, and may use different
colours.

1. (2 pts) Name the functional groups in the following molecules.

O
N
OH
H O

ALCOHOL AMINE ESTER ALKENE

2. (2 pts) The following molecule is the water-soluble form of Valium. Add lone pairs where
necessary to the following structure to create full octets on all the appropriate atoms.
Then add formal charges, where necessary. Finally, state the hybridization and geometry
of the indicated atoms.

H
sp2 N Cl
TRIGONAL PLANAR
N
O

sp2
TRIGONAL PLANAR

3. (1 pt) From the list below, circle the strongest intermolecular force found in iso-propanol.

DIPOLE–DIPOLE HYDROGEN–BONDING ION-DIPOLE

DIPOLE–INDUCED DIPOLE INDUCED DIPOLE–INDUCED DIPOLE

CHM1321 C QUIZ A 2019 Page 2 of 3

4. (4 pts) In the following table, provide the missing IUPAC name or line structure. Clearly
show correct geometry, where necessary.

Name Structure

Z-3-chloro-4-ethyl-2-octene
Cl

O
3,3-dimethyl-oct-6-ynal

5. (3 pts) Clearly draw the two chair conformers of cis-2-ethoxy-cyclohexanol and label the
more stable conformer.

OH H
H OCH2CH3
H
H H
OH
1 H H 6
5 6 2
H 1 H
3 2 OCH2CH3 H 5 4
3
H 4 H
H H
H H
H H
H H

OH is axial, OCH2CH3 is equatorial OCH2CH3 is axial, OH is equatorial

MORE STABLE

NOTE: points will be removed for incorrectly drawn chairs and/if you did not properly show a
chair flip.

6. (3 pts) Draw the line structures both enantiomers of 3-bromo-1-butyne. Label the R and S
isomer.
Br Br

S R
CHM1321 C QUIZ A 2019 Page 3 of 3

7. (3 pts) Consider the various conformers of following molecule along the indicated bond
(the eye shows the desired perspective). Draw and label Newman projections for the
HIGHEST and LOWEST energy conformers of this molecule.

Cl
OH

Cl is the largest group on C1. The cyclopentyl ring is the largest group on C2.

LOWEST ENERGY = HIGHEST ENERGY =

ANTI-STAGGERED FULLY ECLIPSED

H H Cl

HO CH3 H
HO CH3
Cl H

8. (5 pts) Draw CHCF using the LCAO (hybridization) method. Label all the orbitals (p, sp,
sp2, or sp3) and the bonds (σ or π). Include a legend if you’re using different colours.

Legend

1s orbital
πC–C
sp orbital
σC–H
sp3 orbital C σC–C C F
H
σC–F
πC–C
p orbital

FINAL QUIZ SCORE: ________ / 23

CHM1321 C Midterm 1 2019 Page 2 of 11

Part A B C Bonus Total

Points 10 20 20 3 50

Mark

TA

Part A

1. (2.5 pts) Draw the full Lewis structure of CH3ONa. Indicate clearly which bonds are ionic,
non-polar covalent, or polar covalent.

C–H: ∆EN = 2.5 – 2.1 = 0.4 (non polar covalent) H

O–Na: ∆EN = 3.5 – 0.9 = 2.6 (ionic) H C O Na
C–O: ∆EN = 3.5 – 2.5 = 1.0 (polar covalent)
H

2. (3 pts) Give the line structure or the IUPAC names for the following compounds:

STRUCTURE NAME
HO

6-ethyl-7-hydroxy-2-methyl-3-decanone
O

OH
para-chlorophenol
Cl
CHM1321 C Midterm 1 2019 Page 3 of 11

3. (0.5 pt) A Lewis Acid can either act as a Brønsted Acid or as a nucleophile.

TRUE FALSE

4. (0.5 pt) Which of the following Newman projections represents 2-methylhexane?

CH 3 CH(CH 3)2 CH 3 H
H H H 3C H H H H CH2CH 3

H CH 3 H H H 3C H H H
CH2CH2CH 3 CH2CH 3 CH2CH 3 CH 3

A B C D

5. (0.5 pt) You purchase a bottle of Advil (ibuprofen) from Shoppers Drug Mart and test the
optical purity of the product. The sample shows an optical rotation of +23.2º. If the
specific rotation of pure S-ibuprofen is +54.5º, what is the optical purity of Advil?
£ Advil is made of pure R-ibuprofen.
£ Advil is made of pure S-ibuprofen.
¢ Advil is a mixture of 42.5% R-ibuprofen and 57.5% S-ibuprofen.
£ Advil is a mixture of 57.5% R-ibuprofen and 42.5% S-ibuprofen.

6. (1.5 pts) Using the electron-pushing arrows as a guide, draw the expected product(s) of
the following reaction.

H H
O O
O O N
O N
O

7. (1.5 pts) Add lone pairs and electron-pushing arrows as needed to complete the
following reaction:

H H
H H H H
O
+ N
N O
H H H H
H H
CHM1321 C Midterm 1 2019 Page 4 of 11

Part B

8. Consider the various conformers of following molecule along the indicated bond (the eye
shows the desired perspective).
H Br
H F
H 3C F
a. (4 pts) On the following axes, sketch the potential energy diagram (as accurately as
possible) as the FRONT ATOM is rotated CLOCKWISE.

NOTE: While I have included a full analysis below, you only needed to draw the curve.
You will be graded on the relative energy levels of each conformer. In each conformer, I
have put in BOLD the largest group.
H H H CH3 H H
H
F Br F Br F Br F Br F Br F Br F Br
H H 3C CH3
H CH3 H 3C H H H H CH3
F F CH3 F F H F HF F

staggered eclipsed staggered eclipsed staggered eclipsed staggered

1x F CH3 steric strain 1x F CH3 steric strain 2x F CH3 steric strain 1x F CH3 steric strain 1x F CH3 steric strain 1x Br CH3 steric strain 1x F CH3 steric strain
1x Br CH3 steric strain 1x Br CH3 steric strain 1x Br CH3 steric strain

A B C D E F A
Potential Energy

0º 60º 120º 180º 240º 300º 360º

Dihedral Angle

b. (3 pts) Draw the Newman projections for the highest and lowest energy conformers of
this molecule. Label your conformers with the appropriate name from this list: gauche-
staggered; anti-staggered, partially eclipsed; fully eclipsed.

H H
F Br F Br
CH3
H 3C H
F HF

LOWEST ENERGY HIGHEST ENERGY

ANTI-STAGGERED FULLY ECLIPSED
CHM1321 C Midterm 1 2019 Page 5 of 11

9. Aspartic acid (shown at right) is dissolved in a solution at a pH = 7.0. O NH2

OH
HO
a. (0.5 pt) The absolute stereochemistry of the chiral centre in
O
aspartic acid is: R S aspartic acid

b. (0.5 pt) Which of the following will be the major form of aspartic acid at pH = 7.0?

O NH2 O NH3 O NH2 O NH3

OH OH O O
HO HO O O
O O O O

A B C D
c. (2 pts) In the space below, explain your choice.

This molecule contains two different functional groups: a primary amine and two carboxylic
acid groups. The pKa of typical carboxylic acids is about 2 – 5:
O O
H + B + BH
R O R O

Here, the pH of the solution is more basic than the pKa (pH > pKa), so under these
conditions, the deprotonated form is the major species (i.e. [RCOO–] > [RCOOH]). The pKa
of a typical protonated primary amine is about 11:
H
N + BH N + BH
R H R H
H H
Here, the pH of the solution is more acidic than the pKa (pH < pKa), so under these
conditions, the protonated form is the major species (i.e. [RNH3+] > [RNH2]). Putting this
together means that all 3 functional groups will be in their ionized forms.

10. (2 pts) Below is the structure of lysergic acid diethylamide, more commonly known as
LSD. On the right, clearly draw a diastereoisomer of this molecule.

CH 3 CH3 CH3
H H H
N N N
N H N H OR N H
O O O

N N N
CHM1321 C Midterm 1 2019 Page 6 of 11

11. (2 pts) A student is monitoring the reaction below using TLC. On the templates provided,
draw and label a picture of the TLC plate…

O HO OH

+ H 2O

A B
A B A B
CO-SPOT CO-SPOT

a. … after 50% completion. b. … at the end of the reaction.

12. (6 pts) Draw the other possible resonance structures of the ion below, using electron-
pushing arrows to show the conversion between resonance forms. Label the most stable
resonance form, and then draw the resonance hybrid.

OH
H 3C

OH OH OH OH
H 3C H H 3C H H 3C H H 3C H
H H H H
H H H H H H H H
H H H H

MOST STABLE

δ+
OH
H 3C δ+ H
H δ+
H δ+ H
H
CHM1321 C Midterm 1 2019 Page 7 of 11

Part C

13. (4 pts) Clearly indicate the specific relationship (structural isomers, conformers,
enantiomers, diastereoisomers, etc.) between molecule A and structures B through E.

OH OH
OH
OH OH
A B C D E

A and B are: A and C are:

DIASTEREOMERS ENANTIOMERS

A and D are: A and E are:

CONFORMERS STRUCTURAL ISOMERS

14. For the acid-base reaction below:

H
P S P HS
+ +

a. (2 pts) Draw a mechanism and the expected products.

b. (2 pts) Does the equilibrium favour the starting materials or products? Justify your
answer.

This equilibrium favours the REACTANTS. Comparing the two conjugate bases, putting a
negative charge on a SULFUR atom is preferred over the phosphorous atom, due to its
LARGER SIZE, creating a lower charge density. Therefore, the thiol (RSH) is the stronger acid
and the reaction goes to the left.
CHM1321 C Midterm 1 2019 Page 8 of 11

15. (6 pts) Using an MO energy level diagram, show and explain why “F22–” does not exist.
Label all parts of your diagram.

F22– contains 16 electrons. When filled, the MO diagram indicates that there is no net gain to
forming a bond: for every bonding electron there is an anti-bonding electron, resulting in a
bond order of zero!
CHM1321 C Midterm 1 2019 Page 9 of 11

16. (6 pts) Draw the full Lewis structure of BCl3, including lone pairs. What is the hybridization
and geometry of the central atom? What is the overall molecular geometry? What is the
approximate Cl-B-Cl bond angle? Add dipole moment arrows for the bonds in BCl3. Is
this molecule polar or non-polar?

Cl

B
Cl Cl

ATOM HYBRIDIZATION = sp2

ATOM GEOMETRY = trigonal planar

OVERALL GEOMETRY = trigonal planar

ANGLE = 120º

The molecule is NON POLAR.

BONUS – 3 pts

The molecule at right is called 5-hydroxy-1,3-dioxane, and it is an exception to a rule OH

we learned in class: this molecule is more stable with the OH group in the axial
position rather than in the equatorial position. Give a possible explanation why, and O O
support your answer with a chair conformer.

If the hydroxyl group is placed in the axial position, the hydrogen atom can directly form
hydrogen-bonds with the other two oxygen atoms in the ring. Therefore, in this particular
example, these 1,3-diaxial interactions are actually a favourable INTRAmolecular force!
δ+
δ-
H
O
δ-
O H

H
H O H
H
δ-
H
H
CHM1321 C Midterm 2 2019 Page 2 of 13

Part A B C Bonus Total

Points 10 20 20 3 50 (+3)

Mark

TA

Part A

1. (2 pts) Identify the functional group in the following molecules:

CH3
OH HO H
O O

O N H H
CN

HEMI-ACETAL ACETAL IMINE CYANOHYDRIN

2. (3 pts) On the following template, draw the π and π* molecular orbitals for the C=O bond.
Then, show the mechanism and product(s) obtained when this compound reacts with a
nucleophile (Nu).

Blue = π orbital (filled), red = π* orbital (empty). Nu = nucleophile, which can attack from the
top face or bottom face to yield the two stereoisomers.

O Nu Nu O
H 3C
Nu C O +
H H 3C H H 3C H
CHM1321 C Midterm 2 2019 Page 3 of 13

3. (0.5 pt) In an acid-catalyzed nucleophilic addition reaction the role of the acid is to activate
the nucleophile.
TRUE FALSE

4. (0.5 pt) The awesome German word used to indicate a switch in polarity at a carbon atom

(from positive to negative, or visa versa) is ____UMPOLUNG_______.

5. (0.5 pt) Organopotassium reagents are not used as nucleophiles in organic synthesis

because__THEY ARE TOO IONIC, MAKING THEM VERY REACTIVE AND DANGEROUS__.

6. (3 pts) On the axes provided at right, draw a line

Ea2 = 50 kJ/mol
(or curve) representing the reaction profile for a
reaction A à C with the following

ENERGY
Ea1 = 25 klJ/mol
characteristics:
• a two-step mechanism, A à B, then B à C
• Ea of step 2 = 50 kJ/mol
• step 2 is two times slower than step 1 A
• ∆H = –80 kJ/mol B

C
On your profile, label the following: A, B, C, Ea1 ∆H = –80 kJ/mol
(for step 1), Ea2 (for step 2), and ∆H.
REACTION PROGRESS

7. (0.5 pt) Circle the polar aprotic solvent(s) and underline the polar protic solvents:

O OH
CH3OH H 2O
CHM1321 C Midterm 2 2019 Page 4 of 13

Part B
8. (1 pt) Add lone pairs and electron-pushing arrows as needed to complete the following
reaction step:

O O
X + X

(1 pt) In organic chemistry, “X” is called a ____LEAVING GROUP________.

(1 pt) For which of the following possible X substituents would you expect the above step
to take place? Circle all that apply.

CH3 H Br Cl OH H2O NH3 NH2 OCH3

9. (3 pts) Draw the full mechanism and show the final product of the following
transformation. Clearly show stereochemistry (if necessary).
Br O
Br
H 1) 2 equivalents of LiC CCH 3/ether
?
2) H 3O+ /H2O
H H
HO

Br O Br O
Br Br
H H

H H H H
H 3C C C Li H O H 3C C C H Li O
(1st equivalent)
H 3C C C Li
NOTE: back
face attack (2nd equivalent)

O Li
OH Br
Br C CCH 3
C CCH 3
H O H H Br
H Br
2 H 2O + H
H H
H H
Li O
HO H O H
H I’m showing both
protonations at once, but
it’s ok to show them one
at a time.
CHM1321 C Midterm 2 2019 Page 5 of 13

10. (6 pts) Draw a mechanism for the following acid-catalyzed reaction.

O HCl O O
HO OH

H H
O
O H Cl O O H
HO
HO + 3 5
1 2 4 OH
OH
OH
+ Cl

H *note: this proton transfer

step can also be done
H intermolecularly
O O
O O
+ H 2O O
H

OH OH

Cl

O O
+ HCl
CHM1321 C Midterm 2 2019 Page 6 of 13

11. (3 pts) Draw the structures of the compounds A to C below (major organic product only).

LiAlH4/ether H3O+/H2O CH2O/HA

C7H12O2 B C
–H2O O O
A

A B C

O O OLi OLi OH OH

12. The reaction below shows an incorrect final product.

a. (2 pts) Why is this the wrong product? Explain in one or two sentences.
b. (3 pts) Draw the mechanism for the reaction, showing the formation of the correct final
product.
O OH
1) CH 3C CLi (1 equivalent)/ether
A 2)H3O+ /H2O
N N
B
O O

CH 3

The nucleophile adds to the WRONG CARBONYL. Comparing the two electrophiles, labeled
A and B above:
• B is an AMIDE: the partial positive charge on the C atom is REDUCED due to resonance
effects (with BOTH the lone pair on N and the aromatic ring). Additionally, the phenyl
group and methyl groups reduce accessibility at the C atom.
• A is an ALDEHYDE: this carbonyl has greater ease of access (less steric repulsion) and a
larger partial positive charge on the C atom (hyperconjugation only on one side, no
resonance effects).
Therefore, A is the STRONGER ELECTROPHILE and will thus REACT FASTER, leading to
the major product:

CH 3 CH 3
O O C O C
Li C C CH 3 C C
N N N
O O Li OH
H O H
+ H 2O
H
CHM1321 C Midterm 2 2019 Page 7 of 13

Part C
13. (6 pts) For each of the following, provide the missing product or reagents (no
mechanisms). Clearly show stereochemistry where necessary.

H 3C
N
CH3 HCl O
O + N OH
a) OH

O HBr
N + H 2O
NH2
b)

1) NaBH 4 Br
Br
2) H 3O+ /H2O
H
H
OH
H H
O H
c)

14. (2 pts) One of the following statements is false. Select the incorrect statement, and then in
the space below, provide a corrected version.
£ Reduction with lithium aluminum hydride requires a polar aprotic solvent.
£ Addition of a catalyst accelerates both the forward and reverse directions of a reaction.
£ In an acid-catalyzed acetal formation reaction, water must be removed in order for the
reaction to proceed towards products.
£ For safety reasons, in the lab, cyanohydrins are generally formed under acidic
conditions.

For safety reasons, in the lab, cyanohydrins are generally formed under BASIC conditions.
CHM1321 C Midterm 2 2019 Page 8 of 13

15. (3 pts) Provide a possible retrosynthesis for the following, starting from bromobenzene.

D MgBr + D 2O

Br + Mg

16. (4 pts) When cyclohexanone is treated with H2O, an equilibrium is established between
cyclohexanone and its hydrate. This equilibrium greatly favours the ketone, and only trace
amounts of the hydrate can be detected. In contrast, when cyclopropanone is treated with
H2O, the resulting hydrate predominates at equilibrium.
a. Draw both transformations (show the reactant(s) and product(s)).
b. Can you suggest an explanation for the curious observation described above?

O HO OH

+ H 2O

O
HO OH
+ H 2O

PARTIAL RELIEF OF ANGLE STRAIN: in both cases, the carbon atoms in the carbonyl group
begin as sp2 carbons (with ideal bond angles of 120º) and become sp3 carbons (with ideal
bond angles of 109.5º). For cyclohexanone, the bond angles in the hexagon shape are closer
to the ideal than cyclopropanone (only 60º!). Thus, upon hydrate formation, reducing the
bond angle from 120º to 109.5º results in a much larger relief of angle strain in the three-
membered ring.
CHM1321 C Midterm 2 2019 Page 9 of 13

17. (5 pts) The reagent below is diisobutylaluminum hydride, or DIBAL. Like sodium
borohydride, it is a source of nucleophilic hydride. For the following reaction, (with
appropriate work-up) draw both possible products of the reaction; indicate the major
product and provide a justification for your choice. Assign configurations (R or S) to all
stereocentres in the products. Unlike NaBH4, reductions performed with DIBAL require
equimolar amounts of DIBAL and substrate. Can you explain this difference?

R R
OH H
+
H OH
S S
Al + O
H
DIBAL MAJOR MINOR

MAJOR: DIBAL is much bulkier than NaBH4, so it reasonable to assume it will attack the LESS
HINDERED side of the molecule (the back).

NaBH4 provides 4 equivalents of H– (so you only need one quarter of reducing agent); DIBAL-
H on the other hand, has only one hydride to give – thus, you must use as much reducing
agent as the substrate.
CHM1321 C Midterm 2 2019 Page 10 of 13

BONUS (+3 pts)

Draw a mechanism to explain the following transformation.

CH3
H3O+ O H H
O N N
CH3 +
H 2O HO H 3C CH3

CH3 CH3
CH3
O N O N O
H O H CH3 +
CH3 + H N
H CH3
H

H O
H

H H
H O O O O
O H H

HO H

CH3
N
H CH3

O H H
+ N
HO H H 3C CH3