Exam IV May 6, 2025

Do not open the exam booklet until told to start!

Remove the top sheet and answer when told to start.

YOU HAVE 75 MINUTES TO COMPLETE THE EXAM

● A spectroscopy reference table has been provided on the last page of this exam.

● Where relevant, line drawings include all electrons unless the question is specifically
about the number of electrons that should be present.

● This is an exam. You are to complete your work independent of outside help.

● Questions, unless otherwise noted, are 5 points each.

● Make sure to fill out the Name and OCHEM# on the first page, otherwise we will NOT
be able to return your exam booklet.

● “Ph” = phenyl (a benzene ring), equiv. = equivalent, tBu = tert-butyl (C(CH3)3), “Et” =
ethyl, “-OAc” = -CO2CH3

● Pyridine is a non-nucleophilic, weak base often used in acyl group transformations.

HAND IN ALL paper MATERIALS WHEN YOU ARE DONE WITH THE EXAM!

1A 8A Electronegativities of
common elements
H He
1 Li 1.0
Mg 1.2
Li Be B C N O F Ne Cu 1.9
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B 2.0
Na Mg Al Si P S Cl H 2.2
C 2.5
N 3.0
K Ca Ga Ge As Se Br O 3.4
F4
Rb Sr In Sn Sb Te I Cl 3.2
Br 3.0
I 2.7

We suggest that you use pencil to complete the exam

Use the reverse of this page as scratch paper

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OCHEM#: Name:

You must fill out both boxes above for your exam booklet to be returned.

1. Your exam version is A. Please select A in the options on the top-right of your bubble sheet and select A as the
answer to question 1 in the bubble sheet. (2 pts)

2. Select the correct IUPAC name of the molecule shown A. N,N-diethyl-4-hydroxybutan-2-amine

below. B. N,N-diethyl-4-hydroxy-1-methyl propan-2-amine
C. 3-(N,N-diethylamino)butanol
D. 3-amino-3-diethylbutanol

Use the synthetic scheme shown below to answer questions 3-5.

3. Identify the correct major organic product X.

A B C D E
4. Identify the correct major organic product Z.

A B C D E
5. Identify the correct statement about the formation of product Z from Y.

It is an E2 mechanism, and the major product is It is an E1 mechanism, and the major product is less
A. B.
less substituted to avoid steric interactions substituted to avoid steric interactions
It is an E2 mechanism, and the major product is It is an E1 mechanism, and the major product is more
C. D.
more substituted to avoid steric interactions substituted to avoid steric interactions

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6. Select the best statement describing how this
reaction will proceed.

A. The reagent is weakly basic and will therefore react with the carbonyl carbon.
B. The reagent is weakly basic and will therefore react with the β-carbon.
C. The reagent is strongly basic and will therefore react with the carbonyl carbon.
D. The reagent is strongly basic and will therefore react with the β-carbon.

For the following questions #7-10; select the correct reagents given below to complete the scheme. (3 points each)

LDA; CH3OH, 65oC KOH; H2O, 65oC 1. LDA; THF, 0oC

2. H2O, low temp.
A B C D E

For questions #11-#13, select the appropriate sequence of reagents/conditions to complete the synthesis shown. (3
points each)

1. NaOH; H2O 1. NaOCH3; CH3OH 1. LDA; THF, 0oC 1. NaOH; H2O

180oC
2. H3O+; H2O 2. 3-bromopropene 2. 1-pent-5-enyl lithium 2. 3-bromopropene
A B C D E

14. Which of the choices to the right has the least enol
content? (3 points)

15. Which of the choices to the right has the most enol
content? (3 points)

16. Consider the molecules W-Z below. Which two molecules below could efficiently be combined in solution with
hydroxide to give a single mixed aldol condensation product?
A. W and X
B. X and Y
C. W and Y
W X Y Z D. X and Z

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17. Select the correct option to synthesize P as the
major product.

A B

C D Only A and C are correct

E All are correct

For questions #18 and #19, select the correct product for each step of the scheme shown below. (4 points each)

A B C D E

20. Select the major organic product of the following Dieckmann (intramolecular Claisen) condensation.

A B C D

21. Which two changes would be observed via

IR spectroscopy from the substrate to each of
the products shown?

I. The signal at 1650 cm-1 would disappear for W, but would be retained for X A. I and II
II. The signal at 1650 cm-1 would disappear for X, but would be retained for W B. I and III
C. II and III
III. The signal at 1725 cm-1 would disappear for X, but would be retained for W
D. II and IV
IV. The signal at 1725 cm-1 would disappear for W, but would be retained for X
E. III and IV

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22. Select the final organic product for the following reaction sequence.

A B C D

23. Identify the correct organic product.

A B C D E

24. Identify the correct statement about mutarotation

A. Mutarotation is responsible for the interconversion of D-aldotetrose to L-aldotetrose.
B. α-furanose form interconverts to β-furanose form due to mutarotation.
C. α-furanose form interconverts to α-pyranose form due to mutarotation.
D. A and B are both correct
E. B and C are both correct

25. Select the correct precursor (AKA: substrate) for the intramolecular condensation retrosynthesis shown below.

A B

C D

26. Which of the following observations would be

observed in 13C-NMR, comparing the products of
the reactions shown right to the original substrate?

A. The total number of 13C-NMR signals for X would increase from 3 to 5, substrate to product.
B. The total number of 13C-NMR signals for Y would increase from 3 to 5, substrate to product.
C. All 13C-NMR signals for X and Y would move upfield, compared to the substrate
D. A and B would both be observed.
E. B and C would both be observed.

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Use the scheme shown below to answer questions 27-29.

27.Which pyranose structure (P) corresponds to the furanose structure shown above.

A B C D E
28. Based on your choice for Q27, identify the correct name for molecule P.

D-Aldopentose L-Aldohexose D-Aldohexose L-Aldopentose

A B C D
29. Identify the correct statement about product Q.

A Q is optically active. B Q is optically inactive because it is a meso compound.

Q is optically inactive because it is a racemic

C D None of the above.
mixture.

30. Identify the correct statement about tetraalkylammonium salts.

A. They can help solvate insoluble ionic compounds in organic solvents by coordinating to the cation.
B. They can help solvate insoluble ionic compounds in organic solvents by coordinating to the anion.
C. They cannot be used as phase-transfer catalysts.
D. A and B are both correct
E. B and C are both correct

31. Identify the correct self-Claisen condensation product.

A B C D

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32. What changes in stereochemistry would be observed
when the enantiopure molecule shown right is
introduced to mildly acidic water at room temperature?

A. A racemic mixture would result.

B. An equal mixture of two diastereomers would result.
C. An equal mixture of four stereoisomers would result.
D. No definitive conclusions can be drawn from the information presented.

33. Rank the following amines from the most basic to the A V is the most basic and Y is the least basic.
least basic.
B X is the most basic and Y is the least basic.
C V is the most basic and W is the least basic.
D Y is the most basic and V is the least basic.
E X is the most basic and W is the least basic.

34. Select the most feasible pair of Michael addition

precursors (AKA: substrates) for the Robinson annulation
retrosynthesis shown to the right.

A B C D

35. Dr K started with 100 % of molecule Y and added a solution with KOH to it. After a while, she noticed that there was
a new molecule Z along with Y in the solution. Which choice below correctly describes the process observed by Dr K.

A Molecule Y converted to molecule Z via mutarotation.

B Molecule Y converted to molecule Z through multiple keto-enol tautomerizations.
C Molecule Y converted to molecule Z through racemization.
D Molecule Y converted to molecule Z through an aldol addition reaction.
E None of the above.

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36. Identify the correct choice about the equilibrium shown

A. The substituents prefer axial position to avoid unfavorable steric interactions.

B. The substituents prefer axial position because of favorable bonding-antibonding interactions.
C. The equilibrium between the two conformations is due to the mutarotation.
D. Both A and C are correct.
E. Both B and C are correct.

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 Chemical Type of Chemical 13C Data Table Chemical
Proton (1H) NMR DATA TABLE shift (δ), carbon shift(δ) shift (δ) ppm
ppm* ppm* *
Protons bonded to carbon
RCH3 0–35 RCH2Br 20–40
Alkane RCH3, R2CH2, R3CH 0.9–1.8
R2CH2 15–40 RCH2CI 25–50

Allylic 1.5–2.6 R3CH 25–50 RCH2NH2 35–50

R4C 30–40 RCH2OH and RCH20R 50–65
Terminal alkyne H—C≡C 1.8–3.1 RC ≡ CR 65–90 RC≡N 110–125
R2C=CR2 100–150 Esters, amides and
C—H adjacent to C==0 2.0–2.5 carboxylic acid carbonyl 160–185
C
110–175
C—H adjacent to C≡≡N 2.1–2.3 190–220

IR DATA TABLE
Benzylic 2.3–2.8
Structural unit Frequency, Structural unit Frequency, cm-
cm-1 1

Amine 2.2–2.9 Stretching vibrations

Single bonds Double bonds
Alkyl chloride 3.1–4.1 —0—H 3200–3600 1620–1680
(alcohols)
Alkyl bromide 2.7–4.1 —0—H 2900–3100
(carboxylic
acids)
Alcohol or ether 3.3–3.7
3350–3500

Vinylic 4.5–6.5
Aldehydes and 1710–1750
Aryl H—Ar 6.5–8.5 ketones
O Carboxylic 1700–1725
Aldehyde 9–10 acids
R H
Protons bonded to nitrogen or oxygen Acid 1800–1850 and
anhydrides 1740–1790
Amine H—NR2 1–3†
Acyl halides 1770–1815
Alcohol H—OR 0.5–5†
Esters 1730–1750
Phenol H—OAr 6–8†
Amides 1630–1700
Carboxylic acid 10–13† Triple bonds
—C≡C— 2100–2200
Splitting in 1H:
—C≡N 2240–2280
s = singlet d = doublet t = triplet
q = quartet pent = pentet hex = hextet

Ar-H means benzene or benzene-like molecules

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