Sample Exam II CHEM332

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

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

2. Identify the correct statement about the carbon atom in the following molecule

It is a good nucleophile It is a good base but not a It is both a good base and It is not a good base or a
but not a good base good nucleophile a good nucleophile nucleophile
A. B. C. D.

3. Which alkyl chloride below most closely matches this 1H-NMR spectrum?

3H, d
3H, t
2H, pent
1H, hex

A B C D E

4. What is the correct IUPAC name for the following molecule?

Benzenemagnesiumiodide Phenylmagnesiumiodide Magnesiumphenyliodide Iodomagnesiumbenzene

A. B. C. D.

5. Which is the product of the following reaction?

A B C D

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 6. What is the correct IUPAC name A. 1-mercapto-4-phenylbutane- B. 4-mercapto-1-phenyl-butane-
for the following molecule? 2,4-diol 1,3-diol

C. 3-hydroxy-4-mercapto-1- D. 4-phenyl-2,4-dihydroxy-
phenyl-butane-1-ol butane-1-thiol

For the next two questions 7 and 8, select

the major organic product from the choices
below. (4 points each)

No reaction would
be observed.

A. B. C. D. E.

9. Using your understanding of 13C-NMR, which is the correct identity of the compound in the following
spectrum?

4 signals

A B C D

10. In the equilibrium below, which side is favored?

A. The right side, because sulfide anions are more basic than oxide anions.
B. The left side, because sulfide anions are more basic than oxide anions.
C. The right side, because sulfide anions are less basic than oxide anions.
D. The left side, because sulfide anions are less basic than oxide anions.

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11. What are the organic products of the following reaction?

A B C D

12 Tetrahydrofuran and dimethyl oxirane are both ethers.

However, only one can be used as a solvent for reactions
with organometallic reagents. Why?
A. Tetrahydrofuran is too acidic and would be deprotonated by the organometallic reagent.
B. Dimethyloxirane is too acidic and would be deprotonated by the organometallic reagent.
C. Tetrahydrofuran is too electrophilic and would undergo nucleophilic attack by the organometallic reagent.
D. Dimethyloxirane is too electrophilic and would undergo nucleophilic attack by the organometallic reagent.

13. Which one of the following reactions will yield the product shown in the reactions?

A. B.

C. D.

A. NaBH4 can reduce carboxylic acids to 1°-alcohol.

14. Which statement is B. Reduction of carboxylic acids will yield a 2°-alcohol.
true about reducing C. Carboxylic acids are reduced much more easily than ketones and aldehydes.
carboxylic acids? D. Carboxylic acids will always yield 3°-alcohols upon reduction.
E. LiAlH4 reduces carboxylic acids to 1°-alcohols.

15. Identify the correct final organic product of the reaction sequence shown.

A B C D

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16. Which statement correctly describes the major changes
to the IR spectrum compound q under the reaction conditions
provided?

A. The appearance of a strong absorbance at about 1725 cm-1, and the disappearance of a broad
absorbance near 3300 cm-1.
B. The disappearance of a strong absorbance at about 1725 cm-1, and the appearance of a broad
absorbance near 3000 cm-1.
C. The appearance of a strong absorbance at about 1725 cm-1, and the shift of a broad absorbance from
around 3300 cm-1 to around 3000 cm-1.
D. The appearance of a strong absorbance at about 1725 cm-1, and the shift of a broad absorbance from
around 3000 cm-1 to around 3300 cm-1.

17. Identify the major final organic product

of the synthesis scheme shown to the right.

A B C D E

18. Which of the following statements is true about the

carbon depicted in bold in the following reaction?
It is electrophilic in both the reactant and
A B It is nucleophilic in both the reactant and product.
product.

C It’s polarity does not change during the reaction. D It undergoes a polarity reversal during the reaction.

State whether the following three molecules could be formed using Williamson ether synthesis. (2 points each)

#19. #20. #21.

A. Yes B. No A. Yes B. No A. Yes B. No

22. Arrange the following organometallic reagents in the

increasing order of polarity in the carbon-metal bond

I < II < III III < I < II III < II < I II = III = I
A. B. C. D.

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23. In reactions where crown ethers have been added, the role of the crown ether is to...
A. ... be the nucleophile since it is soluble.
B. ... coordinate to the anion of the nucleophile and make the counter-cation nucleophile soluble.
C. ... coordinate to the counter-cation of the nucleophile anion and make the nucleophile soluble.
D. ... help dissolve the electrophile.

24. What would be the major organic product of the following reaction?

A. B. C. D.

For the next three questions, choose the appropriate

reagent/condition combinations, in the correct order
to accomplish the transformation shown on the right.
(3 points each)
K2Cr2O7; H2SO4, Pyridinium dichromate;
H2O CH2Cl2
A B C D E

28. Consider the equilibrium

shown to the right.
A. The reaction will shift in the forward direction, because the pKA of the acidic species decreases.
B. The reaction will shift in the reverse direction, because the pKA of the acidic species increases.
C. The reaction will shift in the forward direction, because the pKA of the acidic species increases.
D. The reaction will shift in the reverse direction, because the pKA of the acidic species decreases.

29. Identify the major final organic product obtained from the square planar intermediate shown below.

A. B. C. D.

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30. Which of the following choices would NOT be an appropriate
set of reagents and conditions for the following transformation?

Pyridinium All of these choices

Pyridinium K2Cr2O7; H2SO4, 1. (CH3)2S=O, (COCl)2; CH2Cl2
Chlorochromate; are feasible for this
Dichromate; CH2Cl2 H2O 2. Et3N
CH2Cl2 reaction
A B C D E

31. Which is the organic product of the following reaction?

A B C D

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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 Frequency, Structural Frequency,
unit cm-1 unit cm-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
Alcohol or ether 3.3–3.7 acids)
3350–3500

Vinylic 4.5–6.5
Aldehydes 1710–1750
Aryl H—Ar 6.5–8.5 and ketones
O Carboxylic 1700–1725
Aldehyde 9–10
R H acids
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 1680–1700
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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