Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Spring 2011

Choose the most correct answer: (4 points each) _____ 1. A To prepare 4-methyl-3-hexanol from a Grignard reaction, you need to use which starting materials? a. 2-bromobutane and propanal b. 2-bromopentane and acetaldehyde c. methyl bromide and 2-pentanone d. 2-bromopentane and propanal e. 1-bromopropane and 2-butanone In the UV-VIS spectra, if the max for CH2=CHCH=CH2 is 300nm, what would you expect the max for CH2=CH2 to be: a. > 300 nm c. = 300 nm e. none of these b. < 300 nm d. 150 nm The ceric nitrate test is used to detect the presence of ________ a. alcohols c. amides b. carboxylic acids d. aldehydes e. amino acids

_____ 2. B

_____ 3. A

_____ 4. B

H 3C CH 3 In the reaction of sodium borohydride with camphor, a. the endo alcohol is the main product because steric hindrance limits the exo approach of the borohydride. b. the exo alcohol is the main product because steric hindrance limits the exo approach of the borohydride. CH 3 O c. ring opening occurs due to the steric influence of the methyl groups. d. the exo alcohol is the main product because steric hindrance limits the endo approach of the borohydride. e. the camphor is reduced to an alkane

_____ 5. B

What type of mechanism is observed for the following reaction?

Cl N Cl N N Cl Cl

N NH2 HN N

N NH3 Cl NH

a. b. c. d. e. _____ 6. C

electrophilic aromatic substitution nucleophilic aromatic substitution E2 elimination SN2 substitution SN1 substitution

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

Chemistry 238

Exam Version A

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Chemistry 238 Spring 2011

Organic Chemistry Laboratory Final Exam Exam Version A

_____ 7. C

An intermediate in the Fischer esterification of benzoic acid and methanol is:

O C
O

O C O

H CH3

a.

d.

H CH3

O
e.

b.

C O

C O CH3

O
c.

H CH3

C O OH

_____ 8. C

Complete hydrolysis of aspartame gives: a. water, alanine and glutamic acid b. water, glutamic acid and phenylalanine c. methanol, aspartic acid and phenylalanine d. methanol, alanine and lysine e. all of these 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

_____ 9. C

_____ 10. Which pair of compounds would react to give one major product through an aldol D condensation reaction upon the slow addition of the two compounds to a basic solution? a. b. c.
O CH3CH2C H O CH3CH2C CH3 O CH3CH2C H + + + CH3CH2OCH3 O CH3C H O CH3C H

d.

e.

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Spring 2011

_____ 11. Which of the following compounds can be reduced by sodium borohydride? D

a. b. c.

CH3CO2H CH3CO2CH3

d. e.

CH3C CH3
CH3CH2OH

O CH3C NH2
5 1 4 3 2

_____ 12. For the following allylic cation, the positive charge will be distributed E on _______. a. only on C1 d. only on C3 b. on C2 and C3 e. on C1 and C3 c. on C3 and C5

_____ 13. A carbonyl compound gave a positive silver mirror test with Tollens' reagent. It also gave a B yellow precipitate in the iodoform test. The compound is most likely: a. 2-propanone d. benzaldehyde b. acetaldehyde e. cyclohexanone c. phenyl acetaldehyde _____ 14. When benzylamine is treated with an excess of methyl iodide, product is: E a.
CH2NH2

d.

CH2NHCH3

b.

CH2NC(CH3)2

e.

+ _ CH2N(CH3)3I

c.

CH2N(I)2

_____ 15. Amides can be prepared by reacting an amine with A a. an acid chloride b. a carboxylic acid c. an aldehyde

d. a bromohydrin e. an alcohol

_____ 16. In order to determine whether the desired product type was produced in the Grignard B Reaction, you obtained an IR spectrum. The main peak looked for 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

Chemistry 238

Exam Version A

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Chemistry 238 Spring 2011

Organic Chemistry Laboratory Final Exam Exam Version A

_____ 17. In the Eschweiler-Clarke reaction, a primary amine reacts with formaldehyde to give an B imine. This imine is then reduced by ______ to give a secondary amine. a. proton transfer from HCO2H b. hydride transfer from HCO2 c. evolution of CO2 d. benzylamine e. an immonium ion _____ 18. A compound forms a 2,4-dinitrophenylhydrazine derivative, gives a positive iodoform test C and a negative result for both the Tollens' and Schiff's tests. This compound is most likely:
O

a. b. c.

CH3CH2CCH(CH3)2 O CH3CH O CH3CH2CCH3

d. e.

OH

_____ 19. Only one major product is observed in the nitration of methyl benzoate. This is due to: C a. the increased reactivity of the meta position compared to benzene b. strong steric effects at the para position c. the relatively low reactivity of the ortho and para positions d. the activating influence of the methyl ester group e. the low temperature at which the reaction is conducted _____ 20. The ester, butyl 2-methylbutanoate, is made by reaction of ________ in the presence of an D acid catalyst. O C a. OH + OH b.
HO O C + OH OH

c.

C OH

OH

d.

OH

OH OH

e.

+
OH

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Spring 2011

_____ 21. What is the product of the following reaction? D

O (CH3)2CH C CH3 + CH3CH2CH2MgBr ether H2O, H+

OH
a.

(CH3)2CH C CH(CH3)2 CH3

O

b.

(CH3)2CH

CH2CH2CH3

OH
c.

(CH3)2CH C CH2CH2CH3 CH2CH2CH3

OH

d.

(CH3)2CH C CH2CH2CH3 CH3

OH
e.

(CH3)2CH C CH2CH2CH3 CH(CH3)2

_____ 22. Which is the best solvent choice for TLC of a three compound mixture of A, B, and C? D Rf of A Rf of B Rf of C a. 10% ethyl acetate 0.12 0.07 0.01 90% hexane b. 20% ethyl acetate 0.34 0.29 0.05 80% hexane c. 30% ethyl acetate 0.53 0.45 0.10 70% hexane d. 40% ethyl acetate 0.72 0.61 0.25 60% hexane e. 50% ethyl acetate 1.0 0.8 0.7 50% hexane _____ 23. When the observed product ratio is controlled by the relative stabilities of the products and E not the relative energies of the transition states leading to the two products, this type of product ratio control is known as a. nucleophilic d. dynamic b. kinetic e. thermodynamic c. electric

Chemistry 238

Exam Version A

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Chemistry 238 Spring 2011

Organic Chemistry Laboratory Final Exam Exam Version A

_____ 24. Which of the following reagents would you use to prepare an intermediate for the synthesis E of benzamide? a. benzene and benzylamine (C6H5CH2NH2) b. benzene and ammonia (NH3) c. benzoic acid and benzyl chloride (C6H5CH2Cl) d. benzoyl chloride (C6H5COCl) and methanol (CH3OH) e. benzoic acid and thionyl chloride (SOCl2) _____ 25. Proteins are made of strings of amino acids joined by peptide bonds. What is another term A for a peptide bond? a. amide bond b. ester bond c. ether bond d. amine bond e. hydrazine bond _____ 26. Arrange the following in order of decreasing reactivity towards the reaction with nitronium A ion. (most reactive to least reactive) a. benzene > methyl benzoate > methyl m-nitrobenzoate b. methyl benzoate > methyl m-nitrobenzoate > benzene c. methyl m-nitrobenzoate > methyl benzoate > benzene d. benzene > methyl m-nitrobenzoate > methyl benzoate e. methyl m-nitrobenzoate > benzene > methyl benzoate _____ 27. At what reaction conditions would the cyanuric chloride yield the product shown below? A

Cl N Cl N N Cl

NH N NH2 HN N NH N

+ n

a. b. c. d. e.

70E C, excess ethylamine 25E C, excess cyanuric chloride 0E C, excess ethylamine 90E C, excess cyanuric chloride 25E C, excess ethylamine

_____ 28. A student spills concentrated sulfuric acid on their hand, what should the student do? B a. go find the TA and let them know what happened b. go to the sink and begin running water over the affected area c. drive themselves to the hospital for the appropriate treatment d. do nothing, sulfuric acid is not harmful e. pour a solution of sodium hydroxide on the hand to neutralize the acid

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Spring 2011

_____ 29. Which test result is considered positive when it produces a wine-purple solution? B a. the Tollens test b. the Schiffs reagent c. the 2,4-DNP test d. the iodoform test e. the preparation of a semicarbazone _____ 30. In the Aldol Condensation lab you performed a computer analysis on the TPCP molecule. B One of the questions asked why the molecule is not completely planar. What prevents this molecule from being planar? a. it is not aromatic b. steric interactions between the phenyl groups c. conjugation is maximized with phenyl groups perpendicular to 5-membered ring. d. attraction between systems of aromatic rings e. 5-membered ring is puckered. _____ 31. Which structure below might reasonably have a fruity odor? C
CO2H

a.
CH3O

b. c.

CH3CH2CH2OCH2CH2CH3 O CH3 CHCH2CH2OCCH3 CH3 CH2OH

d. e.
HCO2H

_____ 32. Why was a sonicator used to start the Grignard reaction? C a. To give kinetic energy to the molecules b. To force the molecules to come together c. To shake off the oxide from the magnesium turnings d. To remove oxygen from the solution e. To heat up the solution _____ 33. Which of the following statements is/are false? D 1. The Eschweiler-Clarke reaction can be used to prepare tertiary amines from primary and secondary amines. 2. Tertiary amines can be produced in good yield by alkylating a primary amine with an alkyl halide. 3. An imine is formed as an intermediate in the Eschweiler-Clarke reaction. 4. Alkylation of secondary amines using excess alkyl halide results in the formation of a quaternary ammonium salt. a. 1 and 3 c. 4 only e. none of these b. 2 and 4 d. 2 only

Chemistry 238

Exam Version A

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Chemistry 238 Spring 2011

Organic Chemistry Laboratory Final Exam Exam Version A

_____ 34. You start the nitration reaction with 6.8 g of methyl benzoate and an excess of other needed D reagents. If you obtain 7.2 g of the expected nitration product, your yield is a. 85 % c. 75 % e. 70 % b. 90 % d. 80 % _____ 35. In comparison to LiAlH4, sodium borohydride is a ______ reducing agent that is capable of D reducing ______. a. milder; amides and carboxylic acids b. more powerful; aldehydes, carboxylic acids, esters and amides c. more powerful; esters, ketones and amides d. milder, aldehydes and ketones e. a and d _____ 36. TLC is a technique easily used for E a. the qualitative monitoring of reactions b. the quantitative monitoring of reactions c. purification of large amounts of an impure compound d. evaluation of the purity of a starting material e. a and d _____ 37. Which statement is NOT correct about THF? E a. Its flammable b. Always handle it under the hood c. Dont contact your skin d. Its a good solvent e. Its not soluble in water _____ 38. Triazine herbicides work by mimicking _______, which is a small molecule involved in E photosynthesis. a. oxidosqualene b. simazine c. chlorophyll d. benzoquinone e. plastoquinone _____ 39. In the aldol condensation of dibenzyl ketone and benzil to form TPCP, __________ first A loses hydrogen to form the enolate. a. dibenzyl ketone b. TPCP c. benzil d. KOH e. ethanol _____ 40. The absorbance of a compound with a concentration 7.5 mM at 330 nm is 1.5. If the path A length was 1 cm, what is the extinction coefficient of the compound at 330 nm? a. 200 M-1 cm-1 b. 20,000 M-1 cm-1 c. 20 M-1 cm-1 d. 2000 M-1 cm-1 e. 2 M-1 cm-1

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Exam Version A

Chemistry 238

Organic Chemistry Laboratory Final Exam Exam Version A

Chemistry 238 Spring 2011

_____ 41. Aspartame, a non-nutritive sweetener, can be written as: B d. H-Arg-Phe-OCH3 a. H-Asp-Glu-OCH3 b. H-Asp-Phe-OCH3 e. H-Thr-His-OCH3 c. H-Val-Asp-OCH2CH3 _____ 42. An unknown compound gives a heavy, yellow-orange precipitate on mixing with 2,4-DNP. C 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.

CH3CH2CH2OH
1

O CH3CH2CH2CH
2

O
c.

H 3C
3

C CH2CH(CH3)2
4 2

O
d. e.

H 3C C H
3 2
1

O CH3CH2
3

C
2

7 4

_____ 43. The hydrolysis of esters can be done by both acid or base catalysis, however esterification of C carboxylic acids can only be done by acid catalysis. Why is this? a. We cannot make a strong enough base to perform the reaction. b. Base will ruin the product produced. c. The carboxylic acid will be deprotonated by the base and will leave an unreactive carboxylate anion. d. The reaction can be catalyzed by base. e. none of these _____ 44. In the addition of the HBr to butadiene, which product is the product of thermodynamic D control? a. 1,4-dibromo-2-butane d. 1-bromo-2-butene b. 3-bromo-1-butene e. 1,2-dibromo-3-butene c. 1-bromo-3-butene _____ 45. In the esterification of benzoic acid with methanol, which of the following statements is true? D 1. The excess methanol increases the yield of the ester. 2. The H2SO4 catalyzes the reaction. e. 1, 2 and 3 3. Adding H2O will increase the yield of the ester. a. 1 only c. 2 and 3 b. 1 and 3 d. 1 and 2

Chemistry 238

Exam Version A

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Chemistry 238 Spring 2011

Organic Chemistry Laboratory Final Exam Exam Version A

_____ 46. In the Borohydride reduction of a ketone experiment, two product alcohols were obtained in E different ratios. Select the correct option for A, B, and C in the scheme below.
H3 C CH 3 NaBH4 EtOH, Heat O A OH H 3C H H3 C CH 3 B

H H 3C OH CH 3

H3 C

H 3C

a. b. c. d. e.

A: Borneol A: Camphor A: Isoborneol A: Camphor A: Camphor

B: Camphor/endo B: Borneol/exo B: Isoborneol/exo B: Isoborneol/endo B: Borneol/endo

C: Isoborneol/exo C: Isoborneol/endo C: Camphor/endo C: Borneol/exo C: Isoborneol/exo

_____ 47. Which of the following statements is false about Grignard Reaction? E 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. _____ 48. Avobenzone and oxybenzone are sunscreen ingredients that both protect against ____ rays. E a. UVB c. UVC e. UVA and UVB b. UVA d. UVA and UVC _____ 49. The electrophile for nitration of an aromatic compound is: A c. NO a. NO2+ b. NO3 d. NO2 e. NO+

_____ 50. In the preparation of simazine experiment you used or produced several compounds. Which A of the following statements about them is false? a. Simazine is more soluble in water than ethylamine. b. Cyanuric chloride is already dissolved in acetone prior to use in the experiment. c. Cyanuric chloride is a solid. d. Simazine is non-toxic to humans. e. Ethylamine and cyanuric chloride are irritants.

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Exam Version A

Chemistry 238