Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Fall 2010

Choose the most correct answer: (4 points each) _____ D 1. Amines are bases because: a. they can stabilize a negative charge b. they are highly electronegative c. they dissolve well in polar solvents d. they have a lone pair of electrons that are easily shared e. none of these Aspartame is used as a ______. People that have the metabolic disorder, PKU, should restrict their intake of aspartame because they lack the enzyme needed to metabolize ______. a. sweetener; phenylalanine d. vapor rub; cysteine b. souring agent; tyrosine e. none of these c. sweetener; valine In the esterification reactions to produce fragrant esters, the catalyst used was? c. Mg e. NaOH a. HNO3 b. H2SO4 d. NaHCO3 A method to make a primary alcohol with a Grignard reagent (R-MgX) is to react the Grignard reagent with: a. a symmetrical ketone R2CO b. an aldehyde R-CHO c. an ester R-CO2R' d. formaldehyde H-CHO e. an unsymmetric ketone R-CO-R' In the formation of tetraphenylcyclopentadienone from 1,3-diphenyl-2-propanone and benzil you used potassium hydroxide and absolute ethanol. The function of the potassium hydroxide in this reaction was to: a. qualitatively remove water b. act as a basic stoichiometric reagent c. act as an acidic catalyst d. act an acidic stoichiometric reagent e. act as a base catalyst By definition, a kinetic product ________, while a thermodynamic product _________. a. forms most quickly; forms less quickly b. is the most stable product; is also the most stable product c. forms most quickly; is the most stable product d. is the most stable product; forms most quickly e. none of these Which reagent(s) may be used for the following reaction?
O O OH CH3CHCH2CH2CH2OH

_____ A 2.

_____ B 3.

_____ D 4.

_____ E 5.

_____ C 6.

_____ A 7.

CH3CCH2CH2COCH3

a. LiAlH4 only b. NaBH4 only c. Grignard reagents only

d. LiAlH4 or NaBH4 e. LiAlH4 or Grignard reagent

Chemistry 238

Exam Version A

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Chemistry 238 Fall 2010

Organic Chemistry Laboratory Final Exam Exam Version A

_____ B 8.

Which is the most likely compound to give 2,4-DNP test (bright yellow color), Tollens test (no silver mirror), Schiffs test (colorless), iodoform test (yellow precipitate)? a. c. e.

b.

d.

_____ C 9.

UV-Vis spectroscopy detects __________ of conjugated systems. a. vibrations b. nuclear transitions c. electronic transitions d. none of these e. all of these

_____ D 10. The purification procedure used to isolate simazine from the reaction mixture would best be described chemically as _____________. a. extraction d. precipitation b. recrystallization e. chromatography c. distillation _____ C 11. The strength of the peptide bond is due to: a. the stability of the amide bond in acidic media. b. the stability of the amide bond in basic media. c. resonance stabilization of the amide bond. d. mobility within a phospholipid bilayer. e. none of these _____ E 12. The nitration of methyl benzoate proceeds through which mechanism? a. SN1 b. SN2 c. E1 d. E2 e. Electrophilic Aromatic Substitution _____ D 13. The following ester is made by esterification of _________. a. 2-methyl propanoic acid and 2-methylbutanol b. 2-methyl propanoic acid and 3-methylbutanol c. 2-methyl butanoic acid and 2-methylpropanol d. 3-methyl butanoic acid and 2-methylpropanol e. 3-methyl butanoic acid and 2-methylbutanol
O

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

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Fall 2010

_____ E 15. The aldol reaction between dibenzyl ketone and benzil is synthetically useful because of which of the following? a. The two carbonyl compounds have similar reactivity. b. There is a large difference in the reactivity of the two compounds. c. They are two different carbonyl compounds which is a requirement for the reaction. d. The product crystallizes from solution and drives the reaction to completion. e. One of the compounds has no -hydrogens. _____ E 16. In the reduction of camphor with NaBH4, two products were obtained. These two compounds may be separated by GC because they are: a. prochiral d. sterically hindered b. enantiomers e. diastereomers c. cyclic compounds _____ E 17. You are trying to carry out the acid-catalyzed esterification of benzoic acid with ethanol. Which of the following would not lead to a higher yield of the ester? a. excess ethanol b. react benzoic acid with thionyl chloride first c. excess benzoic acid d. removal of water by distillation e. removal of ethanol by distillation _____ B 18. The structure of the 2,4-DNP derivative of propanal is:

O
a. b.

CH3CH N

NH C

NH2

CH3CH2CH N

NH O 2N
O

NO2

c.

CH3CH2CH O CH3CH2

CH

C NHNH2

d. e.

C OCH2CH2CH3

O O2N C CH2CH3 NO2

_____ A 19. If a sunscreen has an SPF rating of 5, then everyone wearing it could certainly a. stay in the sun 5 times longer than they could without sunscreen b. be totally protected from UVA c. stay in the sun for 5 hours without tanning d. be totally protected from UVB e. stay in the sun for 5 hours without burning

Chemistry 238

Exam Version A

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Chemistry 238 Fall 2010

Organic Chemistry Laboratory Final Exam Exam Version A

_____ C 20. Chromatographic separations require that compounds partition differently between a mobile phase and a stationary phase. Which combination of mobile and stationary phases were used for chromatographic separations in this lab course? 1. mobile gas, stationary liquid 3. mobile liquid, stationary liquid 2. mobile gas, stationary solid a. 2 only b. 1, 2, 3 and 4 4. mobile liquid, stationary solid c. 1 and 4 e. 1 and 3 d. 1 only

_____ D 21. What is formed when an excess of a methylating reagent, such as methyl iodide or dimethyl sulfate, reacts with a primary amine? a. an imine b. a secondary amine c. a tertiary amine d. a quaternary ammonium salt e. none of these _____ E 22. Nitration of methyl benzoate results in meta-orientation because: a. neighboring group effect b. ortho and para are activated c. meta is activated d. meta is deactivated e. ortho and para are strongly deactivated _____ B 23. What is the name of ester prepared from butyl alcohol and propanoic acid? a. propyl butanoate d. ethyl acetate b. butyl propanoate e. none of the above c. butyl propyl ether _____ E 24. Which of the following could not be used as a solvent in a Grignard reaction?

O
a.

b. CH3OCH2CH2OCH3 c. CH3CH2OCH2CH3 d.

e. CH3OCH2OCH2CH2OH

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Fall 2010

_____ A 25. Which of the following compounds would be deprotonated most easily in an aldol condensation reaction with NaOH?

O
a.

O
d.

CH3 CCH2 CCH2 CH3

CHO
O O

O
b.

CCH2CH(CH2)3

e.

CH3 C

CH2CH3

c.

CH3

_____ E 26. Which of the following carbocations is most stable? a. quaternary c. isobutyl cation b. primary d. secondary _____ B 27. Which of the following cannot be derived from a carboxylic acid? a. b.

e. tertiary

CH3CH2CH2CH2CH2OH

OH O

c.

CH3CH2CN(CH3)2

O
d.

CCl

O
e.

CH3CH2CH2COCH2CH3
O O

_____ B 28. Identify which of the following compounds would give positive iodoform test. 1.
CH3CH2CH2-C-CH3

4.

CH3CH2-C-OCH2CH3

O
2.

O
5.

CH3CH2-C-CH2CH3 O C6H5-C-CH3

C6H5-C-CH3

3.

a. 1, 2 and 5 b. 1, 3 and 5

c. 2 and 4 d. 2 and 3

e. 2, 3 and 4

Chemistry 238

Exam Version A

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Chemistry 238 Fall 2010

Organic Chemistry Laboratory Final Exam Exam Version A

_____ A 29. Which ingredient in sunscreen provides a physical barrier (sun block) to the suns rays, reflecting both UVA and UVB rather than absorbing the energy? a. titanium dioxide (TiO2) d. oxybenzone b. Padimate O e. none of these c. avobenzone _____ D 30. Examine the following reaction:
Cl N Cl N N acetone Cl NH2 Simazine

If we want to convert 1 mole of triazine into simazine, what is the minimum number of moles of ethyl amine we need to use in the above reaction in order to get a maximum yield of simazine? a. 1 mole c. 3 moles e. none of these b. 2 moles d. 4 moles _____ C 31. Which of the following is an imine? a.

CH2NH2

d.

CH2

N(CH3)2
CH3

b.

CH2NHCH3 CH2 N CH2

e.

CH2

N CH2

c.

_____ D 32. Amide bonds may be broken by all of the following except: a. under basic conditions b. under acidic conditions c. enzymatically d. by reaction with dichloromethane e. with trypsin _____ D 33. When performing the nitration of methyl benzoate, methyl m-nitrobenzoate was formed. It is possible to introduce a second nitro group to form the dinitrated product. This was largely avoided because: a. the nitronium ion is not a strong enough electrophile. b. steric hindrance would not allow a second bulky NO2 to react with the ring. c. the reaction is carefully timed so that no dinitration is possible. d. the first NO2 group introduced has a strong deactivating effect so that the addition of a second group is more difficult. e. the nitration mixture that was used is weak and therefore highly selective.

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Fall 2010

_____ D 34. Which of the following is the LEAST volatile? a. methyl alcohol c. methyl formate b. ethyl acetate d. methyl salicylate

e. ethyl pentanoate

_____ C 35. What would be the expected final product from the reaction of a ketone with a methyl Grignard reagent, followed by hydrolysis? a. primary alcohol d. ester b. secondary alcohol e. none of these c. tertiary alcohol _____ B 36. What are the products of the following reaction?
HBr

?
Br

Br
Br

Br

I. a. I and II b. I and III

II. c. I and IV d. II and III

III.

IV. e. II and IV

_____ C 37. In the sodium borohydride reduction of camphor, isoborneol is the major product owing to: a. solvent effects b. electronic effects c. steric effects d. isotope effects e. none of these, borneol is the major product _____ A 38. 9.0 g of benzoic acid (MW = 122) reacts with 18 g of methanol (MW = 32) in the presence of an acid to give 7.0 g of methyl benzoate (MW = 136). What is the percent yield? a. 69.8 % c. 51.6 % e. 86.7 % b. 45.7 % d. 77.8 % _____ E 39. Which of the following is a suitable reagent that will quickly distinguish between pentanal and 3-pentanone? c. NH2OH e. Ag(NH3)2+ OH a. Na metal d. 2,4-DNP b. Br2/CCl4 _____ C 40. How are triazine herbicides prepared? a. electrophilic aromatic substitution b. SN2 c. nucleophilic aromatic substitution d. dehydrohalogenation e. SN1 _____ D 41. A Schiff base (imine) was an intermediate in the synthesis of which of the following? a. tetraphenylcyclopentadienone d. N,N-dimethylbenzylamine b. methyl m-nitrobenzoate e. methyl benzoate c. simazine

Chemistry 238

Exam Version A

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Chemistry 238 Fall 2010

Organic Chemistry Laboratory Final Exam Exam Version A

_____ A 42. 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 _____ A 43. During the nitration of methyl benzoate experiment your TLC plate was spotted with the crude product, the mother liquor, and the recrystallized product. When observing the plate under the UV lamp, how many spots would you expect to see for the recrystallized product. a. 1 c. 3 e. 5 b. 2 d. 4 _____ A 44. The reaction of C6H5MgBr with water produces: c. C6H5Br a. C6H6 b. C6H5OH d. diphenyl

e. all of these

_____ B 45. Which of the following compounds can undergo an aldol reaction with itself? O O d. H C a. C H NO2
H O C C
H

b.

e.

O HO C

c.

O C

_____ B 46. 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?
CH
CH H2 C
CH3 CH 2 CH

CHCH 3 CH2
CH CH 2

CH 2CH 3 CH

H2 C

C H2 C CH2

CH 2CH 3

CH H2 C CH

CHCH 3

a. 5 b. 4

c. 3 d. 2

e. 1

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Fall 2010

_____ B 47. When you reduce NH2CH2COCH=CHCO2CH3 with NaBH4/EtOH, the resulting compound would be:

a.

H2NCH2C CH2 CH
OH H2NCH2CH
OH

CHCH2OH
CHCO2CH3

b. c.

CH2 CH

H2NCH2CH2 CH2 CH
H2NCH2CH CH2 CH OH H2NCH2CH CH2 CH

CHCH2OH
CHCH2OH CHCH2OCH3

d.

e.

_____ A 48. Which of the following carbonyl compounds is most reactive toward nucleophilic acyl substitution? a. alkyl acid chlorides b. esters c. aromatic acid chlorides d. amides e. carboxylic acids _____ C 49. What is the absorbance at 310 nm of a solution of 0.00250 g of Oxybenzone, MW=228.2 g/mol, in 5.0 mL of isopropyl alcohol. The molar extinction coefficient (at 310 nm) of Oxybenzone is 575 and the cuvette has a path length of 1.00 cm. H3CO a. 0.00126 b. 0.287 c. 1.26 d. 1.37 e. 287.5

O C OH oxybenzone

_____ E 50. Triazine herbicides act by: a. inhibiting chlorophyll synthesis resulting in disruption of photosynthesis b. oxidation of cell membrane liquids c. disrupting cell division of roots d. inhibiting the enzymes of lipid biosynthesis e. blocking electron transport to plastoquinone in the photosynthesis process

Chemistry 238

Exam Version A

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