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Chemistry 238 – Spring 2015 Final Examination – Form A

Choose the most correct answer: (4 points each)

1. The solution into which the fabric was placed in the indigo experiment was:
a. Deep blue c. Clear e. a and d
b. Purple d. a cloudy suspension

2. Which test results as positive for aldehydes by producing a wine purple solution?
a. the Schiff’s reagent
b. the Tollens’ test
c. the 2,4 DNP test
d. the iodoform test
e. the preparation of a semicarbazone

3. For the following allylic cation, the positive charge will be distributed _______.
a. only on C1
b. on C2 and C3 5
c. on C3 and C5 1
d. only on C3 3
4 2
e. on C1 and C3

4. In the Fischer esterification experiment, 3.0 g of benzoic acid (MW = 122) was heated with 5.5 g
of methanol (MW = 32) in the presence of 3 mL of sulfuric acid. After work up and purification,
1.8 g of methyl benzoate was obtained. The percent yield for this reaction is
a. 20% c. 54% e. 67%
b. 33% d. 60%

5. When you reduce NH2CH2COCH=CHCO2CH3 with NaBH4/EtOH, the resulting compound would
be:
O
a. H2NCH2C CH2 CH CHCH2OH
OH
b. H2NCH2CH CH2 CH CHCO2CH3

c. H2NCH2CH2 CH2 CH CHCH2OH

OH
d. H NCH CH CH CH CHCH2OH
2 2 2
OH
e. H NCH CH CH2 CH CHCH2OCH3
2 2

Form A – Page 3
Chemistry 238 – Spring 2015 Final Examination – Form A

6. Excess ethylamine is needed in the synthesis of simazine in order to:

a. ensure complete nucleophilic substitution of the cyanuric chloride
b. neutralize the acid formed by the substitution reaction
c. generate the nucleophilic Cl– ion to effect the substitution reaction
d. neutralize the acidic cyanuric chloride
e. form an amine salt with the simazine product

7. What is the product of the following reaction?

O
a.
OH

b.

c.

d.

e.

8. In the aldol condensation lab, you examined a molecular model of the aldol product, tetra
phenylcyclopentadienone, TPCP. The model showed that the phenyl groups were not in the
same plane as the cyclopentadienone ring or the other phenyl groups.
What is the major factor preventing a planar structure from being lowest in energy?
a. steric interactions between atoms on the phenyl rings when in the same plane
b. orbital overlap is reduced in the all planar structure
c. conjugation is maximized when the phenyls are perpendicular with the central ring
d. molecular size is reduced when they are out of plane
e. the computer can’t calculate accurate structures

9. A carbonyl compound gave a positive silver mirror test with Tollens' reagent. It also gave a
yellow precipitate in the iodoform test. The compound is most likely:
a. 2 propanone d. acetaldehyde
b. phenyl acetaldehyde e. cyclohexanone
c. benzaldehyde

Form A – Page 4
Chemistry 238 – Spring 2015 Final Examination – Form A

10. Which of the following statement(s) is/are correct?

a. Thermodynamic control results in more stable intermediate/product being formed.
b. Thermodynamic control results in the fastest intermediate/product being formed.
c. Kinetic control results in more stable intermediate/product being formed.
d. Kinetic control results in the fastest intermediate/product being formed.
e. a and d are correct

11. Low molecular weight esters have fruity flavors and odors. Why do esters, which have higher
molecular weights than carboxylic acids, have lower boiling points than the carboxylic acids they
were made from?
a. Carboxylic acids are solids and harder to liquify than their esters.
b. Carboxylic acids have much stronger intermolecular Van der Waals forces.
c. Most carboxylic acids exist as dimers which are held together by two hydrogen bonds.
d. Ester molecules have strong hydrogen bonding forces with other ester molecules which
helps increase their volatility.
e. Boiling points of all organic esters decrease with increasing molecular weight.

12. Complete the following reaction:

1.
2.
OH + H

O H OH

a. 1.) K2Cr2O7 2.) H+

b. 1.) H2O2 2.) OH
c. 1.) NaHCO3 2.) H2O
d. 1.) NaBH4 2.) H2O
e. 1.) O3 2.) Zn, ether

13. Which one is not a derivative of carboxylic acids?

a. esters
b. carboxylic acid anhydrides
c. acid chlorides
d. amides
e. Schiff’s base

Form A – Page 5
Chemistry 238 – Spring 2015 Final Examination – Form A

14. In order to determine whether the desired product type was produced in the Grignard Reaction,
you obtained an IR spectrum. The main peak expected to be present was at approximately:
a. 2400 2580 cm 1 d. 3010 3100 cm 1
1
b. 3200 3600 cm e. Fingerprint Region
1
c. 1700 1720 cm

15. What could be the reason(s) for a ‘bad’ TLC.

a. Did not spot enough sample.
b. Did not wait for the sample spot to dry before spotting the second time.
c. The spots were arranged too close to each other on the TLC plate.
d. a and b
e. a, b and c

16. Which of the following compounds will not undergo an aldol reaction with itself?
O O
1. C H 4.
CH3 C H

O
O
2. O2N C H 5.
CH3 C CH2CH2OH

O
3. CH2 C

a. 1 and 3
b. 2, 3 and 4
c. 1, 2 and 4
d. 1 and 2
e. 2, 4 and 5

17. Identify which of the following compounds would give positive iodoform test.

1. 4.

2. 5.

3.

a. 1, 2 and 5
b. 1, 3 and 5
c. 2 and 4
d. 2 and 3
e. 2, 3 and 4

Form A – Page 6
Chemistry 238 – Spring 2015 Final Examination – Form A

18. In the hydrolysis of the artificial sweetener, aspartame, you produced two different amino acids.
Which of the following structures would be the correct ionic structure for one of them at an
acidic pH 3.0?

a. d.

b. e.

c.

19. A mixture of nitric acid and sulfuric acid was added to an equimolar mixture of C6H6, C6H6Z,
C6H6Y. After warming and stirring for a few minutes the nitrated products were analyzed and
found to consist of the products C6H4YNO2, C6H5NO2, and C6H4ZNO2 in the ratio of 750:30:1,
respectively. Which of the following can be deduced from this data?
a. the Z group is a deactivator
b. the nitro group is a meta director
c. the Y group is a deactivator
d. benzene is the least reactive
e. the Z group is an ortho para director

20. In the NaBH4 reduction of camphor:

a. The NaBH4 reduced the carbonyl group by adding a proton (H+) to the carbonyl carbon.
b. The NaBH4 reduced the carbonyl group by adding a hydrogen atom (H ) to the carbonyl
carbon.
c. The NaBH4 reduced the carbonyl group by adding hydride (H:–) to the carbonyl carbon.
d. The NaBH4 provided a catalytic surface for the one step addition of a hydrogen molecule
(H2) across the carbonyl double bond.
e. The NaBH4 reacted with ethanol to give (CH3CH2OH2)– which was the actual reducing
agent that attacked camphor.

Form A – Page 7
Chemistry 238 – Spring 2015 Final Examination – Form A

21. The reaction shown proceeds until it reaches equilibrium.

Which of the following will increase the yield of the ester?

I. using an excess of methanol

II. using an excess of benzoic acid
III. adding water to the reaction flask
IV. removal of the water and methyl benzoate
V. using more concentrated sulfuric acid
a. I, III and V
b. II, IV and V
c. I, III and IV
d. I, II and V
e. I, II and IV

22. Which of the following statements is false about Grignard Reaction?

a. The Grignard reagent may be viewed as a strong base.
b. Grignard reagents are prepared by the reaction of alkyl or aryl halides with magnesium.
c. Grignard reagents are most often used in reactions with aldehydes or ketones.
d. Grignard reagents react with acids to give alkanes.
e. Alcohols are often used as solvents in the Grignard Reactions.

23. UV VIS light interacts with which of the following?

a. vibrations of molecular bonds
b. electronic transitions
c. nuclear transitions
d. molecular weights
e. hydrogen bonding

24. In the Preparation of Organic Dyes, which position does the aryl diazonium ion most prefer to
add to a phenol molecule?
a. no obvious preference
b. ortho and para position
c. ortho position
d. para position
e. meta position

Form A – Page 8
Chemistry 238 – Spring 2015 Final Examination – Form A

25. In the aldol condensation of dibenzyl ketone and benzil, benzil serves as:
a. a source of enolate ions
b. a base for abstraction of a proton from dibenzyl ketone
c. an electrophile for attack by hydroxide to give the reactive nucleophile
d. an electrophile for reaction with an enolate ion
e. a nucleophile for reaction with an enolate ion

26. The hydrobromination (Addition of H Br) of the following compound at room temperature gives
a major product and a minor product. Predict the products and indicate whether they are kinetic
or thermodynamic product

a. d.

b. e.

c.

Form A – Page 9
Chemistry 238 – Spring 2015 Final Examination – Form A

27. Which is the best reagent for detecting amino acids on TLC plate?
a. a ninhydrin solution
b. a potassium permanganate solution
c. a ceric ammonium nitrate solution
d. Schiff's reagent
e. Dragendorff's reagent

28. Why is H2SO4 used during the nitration of methyl benzoate?

a. It is a catalyst that protonates the aromatic ring.
b. It is used to help dissolve methyl benzoate.
c. It is a catalyst that protonates nitric acid.
d. It is a deactivating agent that will prevent the formation of methyl dinitrobenzoate.
e. H2SO4 is not used during the nitration.

29. What is the name of this starting material used in the preparation of a triazine herbicide?
a. chlorotriazole
b. cyanuric chloride
c. trinitrobenzene trichloride
d. chloro azobenzene
e. cyclocyano trichloride

30. An intermediate in the Fischer esterification of benzoic acid and methanol is:
O
a. C

H
O H
b. C O
CH3
H
O H
c. C O
OH CH3
O H
d. C O
CH3
O
e. C O CH3

Form A – Page 10
Chemistry 238 – Spring 2015 Final Examination – Form A

31. Why is an ethereal solvent such as diethyl ether or THF used in the Grignard Reaction?
a. The lone pairs allow the Grignard reagent to dissolve into solution.
b. They are polar solvents and will form a different layer when you want to separate the
product form solution.
c. They are safer than alternative solvents.
d. They prevent the formation of an emulsion during the reaction.
e. They produce a desirable side reaction that forms carboxylic acids.

32. Which is the general category of compounds that are the common active ingredients in sun
screens?
a. unconjugated aromatic compounds
b. unconjugated aliphatic compounds
c. fatty acids
d. conjugated aliphatic compounds
e. conjugated aromatic compounds

33. Which would be the product isolated from the aldol condensation of cyclopentanone?
O O
a. d.

O HO
O
b. e.

O
c.

Form A – Page 11
Chemistry 238 – Spring 2015 Final Examination – Form A

34. An unknown compound gives a yellow precipitate on mixing with 2,4 DNP. Treatment with the
iodoform reagents yields a yellowish precipitate with a strong, medicinal odor. No particular
change in appearance is observed in running the Tollens' test. If the unknown is one of the
following compounds, it is most probably:
a.

b.

c.

d.

e.

35. In the Peptide and Amino Acids lab, aspartame was heated to form a diketopiperazine and what
side product?
a. acetic acid
b. benzoic acid
c. ethanol
d. hexanol
e. methanol

36. Choose the correct statement that compares the reactivity of acetanilide to ethylbenzoate
toward electrophilic aromatic substitution.

CO2CH3 NHCOCH3

a. Acetanilide is less reactive toward electrophilic aromatic substitution owing to the

electron withdrawing group attached to the aromatic ring.
b. Ethyl benzoate is more reactive toward electrophilic aromatic substitution owing to the
electron withdrawing group attached to the aromatic ring.
c. The reactivities are approximately the same because both compounds have electron
withdrawing substituents.
d. Acetanilide is more reactive toward electrophilic aromatic substitution owing to the
electron donating group attached to the aromatic ring.
e. Ethyl benzoate is less reactive toward electrophilic aromatic substitution owing to the
electron donating group attached to the aromatic ring.

Form A – Page 12
Chemistry 238 – Spring 2015 Final Examination – Form A

37. In the borohydride reduction of camphor isoborneol is the major product because:
a. attack of borohydride from the less hindered exo side gives the endo alcohol.
b. attack of borohydride from the less hindered endo side gives the endo alcohol.
c. attack of borohydride from the less hindered exo side gives the exo alcohol.
d. attack of borohydride from the less hindered endo side gives the exo alcohol.
e. attack of borohydride from the more hindered endo side gives the exo alcohol.

38. The product of the following reaction is

a. d.

b. e.

c.

39. In a Grignard reaction, 3 methyl 3 heptanol can be made from ______.

a. 2 butanone and 1 bromopentane
b. 2 butanone and 1 bromobutane
OH
c. 2 pentanone and 1 bromobutane
d. 2 pentanone and 1 bromopropane
e. 2 butanone and 1 bromopropane

40. The type of UV light that one might receive on a sunny day that gives rise to immediate sunburn
is:
a. UVC c. UVA e. a and c
b. UVB d. a and b

Form A – Page 13
Chemistry 238 – Spring 2015 Final Examination – Form A

41. In an aqueous organic extraction,

a. the less dense layer is on top
b. the more dense layer is on top
c. aqueous layer is always on top
d. the phase with less sample dissolved is always on top
e. the organic layer is on top

42. The reaction to form azo dyes is an example of what type of reaction?
a. Nucleophilic aromatic substitution
b. Nucleophilic acyl substitution
c. SN2 substitution
d. Electrophilic addition
e. Electrophilic aromatic substitution

43. Which test would be positive for the following compound: CH3CH CHCH2CCH3
I. Iodoform test II. Schiff’s test III. Baeyer
IV. Copper Acetylide V. Bromine
a. I and III
b. I, III and V
c. III and IV
d. II and IV
e. all five

44. Remember that a single resonance stabilized compound or intermediate may be represented by
any of the individual hybrid structures. How many different cationic intermediates are
represented by the structures below?

1. 4.

2. 5.

3.

a. 3
b. 5
c. 4
d. 1
e. 2

Form A – Page 14
Chemistry 238 – Spring 2015 Final Examination – Form A

45. What is the name of ester prepared from butyl alcohol and propanoic acid?
a. propyl butanoate
b. butyl propanoate
c. butyl propyl ether
d. ethyl acetate
e. none of the above

46. In the nitration of methyl benzoate the rate of attack by the electrophile is:
a. increased by the CO2 CH3 group and directed to the ortho and para positions.
b. slower than if the CO2 CH3 substituent were not present, and the addition is directed to
the ortho and para positions.
c. Increased by the CO2 CH3 group and directed to the meta position.
d. slower than if the CO2 CH3 substituent were not present, and the addition is directed to
the meta position.
e. facilitated by the addition of the NO2 substituent which then directs dinitration to the
ortho and para positions.

47. Triazine herbicides work by mimicking ______, which is a small molecule involved in
photosynthesis.
a. oxidosqualene
b. simazine
c. chlorophyll
d. benzoquinone
e. plastoquinone

48. Why is an excess of CH3OH used in making methyl benzoate from benzoic acid?
a. to shift the equilibrium toward reactants
b. to increase the percent yield by acting as a catalyst
c. to increase the percent yield by shifting the equilibrium toward products
d. to make the separation of products from reactants easier
e. to make the reaction mixture easier to reflux

Form A – Page 15
Chemistry 238 – Spring 2015 Final Examination – Form A

49. Which Grignard reagent below will react with 2 butanone to form 3,5 dimethyl 3 hexanol?
CH3CHCH2MgBr
a.
CH3

b. CH3CH2CH2CH2CH2MgBr

CH3
c. CH3 C CH2MgBr
CH3

d. CH3CH2MgBr

CH3
e. CH3CH CHMgBr
CH3

50. Which of the following statements about the SPF, sunscreen protective factor, values for
sunscreens is false?
a. you should choose the SPF based on your skin type and the amount of time you plan to
be in the sun
b. as SPF values increase, you get better UVB protection for the same amount of time in
the sun
c. as SPF values increase you can stay longer in the sun before you start getting sunburn
d. SPF refers to product effectiveness against both UVA and UVB radiation
e. SPF = (MED for the skin with sunscreen)/(MED for skin without sunscreen), where MED
is minimal erythemal dose

Form A – Page 16
Chemistry 238 – Spring 2015 Final Examination – Form A

Form A – Page 17
Chemistry 238 – Spring 2015 Final Examination – Form A

Form A – Page 18