CHM 2211 Organic Chemistry II

KEY

Final Exam Review Questions

Examples of the types of questions you can expect to see on the final

1.

The IUPAC name for the formula CH3CH2CH2CHOHCH=CH2 is 1. 2. 5. 5-hexene-3-ol 1-hexene-5-ol allyl n-butyl ether 2. 4. 1-hexene-3-ol n-propyl ally alcohol

2.

What is the order of reactivity toward SN2 displacement in the following series? A.
CH3

B.
CH3 CH2 CH2 CH2 Cl

C.
Cl CH3 CH2 CH CH3

CH3 CH2 C CH3 Cl

1. 3. 5. 3.

A>B>C B>A>C C>A>B

2. 4.

A>C>B B>C>A

The principal organic product formed in the reaction below is

CH2 =CH(CH2 )8 COOH + HBr peroxide

1. 3. 5. 4.

CH3CHBr(CH2)8COOH CH2=CH(CH2)8COBr none of these

CH3 CH3 C CH2 OH CH3

2. 4.

CH2BrCH2(CH2)8COOH CH2=CH(CH2)7CHBrCOOH

Treatment of

with HCl gives

1. CH3 CH2 CH2 CH2 CH2 Cl

2.

CH3 CH3 CH2 CH CH2 Cl

CH3

3.

CH3 CH2 C CH3 Cl

4.

CH3 CH3 CH CH3

5.

CH3 CH3 CH CH2 CH2 Cl

5.

A compound which is insoluble in cold, concentrated sulfuric acid is 1. 3. 5. n-hexane 2-hexyne benzyl alcohol 2. 4. 1-hexene ethyl acetate

6.

Which reagent would convert cyclohexene into a cis-glycol? 1. 2. 3. 4. 5. sodium tert-butoxide in chloroform hydrogen peroxide and aqueous acetic acetic acid ozone and moist zinc dust periodic acid cold dilute potassium permanganate

7.

Which statement is correct for an SN1 reaction at a chiral carbon atom? 1. 2. 3. 4. 5. the product will be optically active, but have the opposite configuration the reaction will involve racemation a carbanion is formed as an intermediate the rate of the reaction is a function of the concentration of the nucleophile the attacking group will be a strong electrophile

8.

Which does NOT involve a carbocation? 1. 2. 3. 4. (CH3)3CCl + AgNO3 (CH3)3COH + HCl (CH3)3CH + Cl2 + uv light CH3CH=CHCH2OH + H3O+

9.

The reagent which would distinguish between 1-hexyne and 1-hexene is 1. 3. 5. Ag(NH3)2+ Br2 in CCl4 NaOH 2. 4. KMnO4 H2SO4

10.

In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH2CH2OCH3 in addition to 1,2-dibromoethane because 1. 2. 3. 4. 5. the methyl alcohol solvates the bromine. the ion formed initially may react with Br1- or CH3OH. this is a free radical reaction. the reaction follows Markovnikovs rule. of none of these reasons.

11.

The important minor product from the reaction of sodium cyanide with 2-iodopentane in anhydrous acetone is 1. 3. 5. 1-pentene pentane 4,5-dimethyloctane 2. 4. 2-pentene 2-pentanol

12.

The monochloroisomer that predominates in the mixture resulting from the free radical chlorination of CH3CH2CH2CH=CH2 is 1. 3. 5. ClCH2CH2CH2CH=CH2 CH3CH2CHClCH=CH2 CH3CH2CH2CH=CHCl 2. 4. CH3CHClCH2CH=CH2 CH3CH2CH2CCl=CH2

13.

When a solid organic compound is recrystallized, the cold filtrate from the cooled mixture is 1. 3. 5. saturated with the compound. 2. entirely free of the compound. 4. supersaturated with the compound. an unsaturated solution of the compound. pure solvent.

14.

Sodium iodide in anhydrous acetone reacts most rapidly with 1. 4. CH3CH2CH2Br CH2=CHBr 2. 5. (CH3)3CBr
CH3 Br

3.

Br

CH3 CH CH3

15. CH3CH=CHCH2OH reacts with HBr to give which two bromobutenes? 1. 2. 3. 4. 5. CH3CH=CHCH2Br CH3CH=CHCH2Br + CH3CH=CBrCH3

+ CH3CHBrCH=CH2

CH2=CHCH2CH2Br + CH2=CHBrCH=CH2 CH2=CBrCH2CH3 BrCH2CH=CHCH3 + CH2=CHCH2CH2Br + BrCH2CH2CH=CH2

16.

What is the possible number of stereoisomers having the structure below?

OH OH

CH3 CH CH2 CH CH3

1. 2. 3. 4. 5.

two optically active and one meso None optically active four optically active two optically active and two meso one optically active and one meso

17. The addition of Br2 to trans-2-butene giving meso-2,3-dibromobutane can be explained by a mechanism involving 1. 3. 5. 18. a free radical. 2. a carbocation. a cyclic bromonium ion. 4. a carbanion. simultaneous attack by to bromine atoms.

Which metal catalyzed reaction would release the greatest amount of heat per CH2 unit? 1. 2. 3. 4. 5. cyclopropane + H2 propane cyclobutane + H2 cyclopentane + H2 cyclohexane + H2 cyclododecane + H2 butane pentane hexane dodecane

19. What is the IUPAC name for the compound shown below?
CH3 CH3

CH3 CH CH C CH3

1. 2. 3. 4. 5. 20.

2,3-dimethyl-4-pentene 1,1-dimethyl-2-isopropylethene 2,3-dimethyl-2-pentene All of the above None of the above

Which dimethylcyclobutane has two optically forms? 1. 3. 5. trans-1,2trans-1,31,12. 4. cis-1,2cis-1,3-

21.

The C-C-N angle in acetonitrile, CH3CN is 1. 4. 45 120 2. 5. 60 180 3. 109.28

22.

Which is NOT characteristic of a free radical chain reaction? 1. 2. 3. 4. 5. It produces a mole of product for a mole of free radical initiated. It gives the product derived from the most stable free radical. It may be initiated by peroxides. It may be initiated by high heat. It may be initiated by ultraviolet light.

23.

A reaction at a chiral carbon of an optically pure isomer which takes place exclusively by an SN2 reaction, and in which priorities do not change, proceeds with 1. 2. 3. 4. 5. inversion and no racemization. inversion and some racemization. inversion and complete racemization. retention of configuration and some racemization. retention of configuration and no racemization.

24. Which would yield 2-methyl-2-pentene when refluxed with zinc dust in alcohol? 1.
Br CH3

2.

Br

CH3

CH3 CH2 CH C CH3 Br

CH3 CH2 CH CH CH3

3.

CH3 CH3 CH2 CH2 C CH2 Br Br

4.

Br CH3 CH3 CH2 C CH CH3 Br

5.

Br

Br

CH3

CH3 CH CH CH CH3

25.

Which anion is the weakest base? 1. 3. C2H5O1CH3COO12. 5. NO31OH13. CN1-

26.

Which compound would be the major product when (CH3)2CHCHBrCH2CH3 is treated with alcoholic KOH? 1. 3. 5. (CH3)2CHCH2CHOHCH3 (CH3)2COCH2CH2CH3 (CH3)2C=CHCH2CH3 2. 4. (CH3)2CHCHOHCH2CH3 (CH3)2CHCH=CH3

27. If tert-butyl bromide and sodium amide (NaNH2) react, the product formed is 1. 2. 3. 4. 5. 28. tert-butylamine. (amines are R-NH2) tert-butylammonium bromide. a mixture of butylamines. isobutylene. (2-methylpropene) none of these.

In the reaction below, the product would be

CH3 CH CH CH3 + H2 O H3 O+ OH CH3 CH2 CH CH3

1. 2. 3. 4. 5. 29.

a mixture of diastereomers. opticaly active. unresolvable. a racemate. a meso compound.

The rate of an SN2 reaction run in a polar aprotic solvent relative to the same reaction in a polar protic solvent would be 1. 2. 3. 4. 5. the same. slower. faster. unpredictable. unimolecular.

30.

Which of the amines listed below would have the lowest boiling point? 1. 3. 5. CH3CH2CH2NH2 (CH3)3N (CH3)2CHNH2 2. 4. CH3CH2NHCH3 (CH3)3CNH2

31.

Racemic 2,3-dibromobutane can be made by adding bromine to 1. 3. cis-2-butene. 1,3-butadiene. 2. 4. 1-butene. trans-2-butene.

32.

Which species represents the electrophile in aromatic substitution? 1. :NO22. NO2+ 3. NO2 4. NO35. SO3H+

33.

Which could NOT be prepared directly from 4-bromobenzene-diazonium ion? 1. 3. 5. Phe-Br 4-Br-Phe-F 4-Br-Phe-COCH3 2. 4. 4-Br-Phe-Br 4-Br-Phe-CN

34.

A good starting material for the preparation of 4-chlorobenzenesulfonic acid would be 1. 3. 5. benzenesulfonic acid chlorobenzene 1,4-dichlorobenzene 2. 4. 1,4-dinitrobenzene 4-chlorobenzioc acid

35.

Which represents an intermediate formed in the reaction of toluene and chlorine at elevated temperature in sunlight? 1.
H CH3 Cl

2.

H CH3 Cl

3.
CH2

4.
CH2

5.

H CH3 Cl

36. The reaction of benzyl chloride with sodium isopropoxide yields 1. 3. 5. 37. benzaldehyde and 2-chloropropane 2. 1,2-diphenylethane and acetone acetone and toluene 4. benzyl isopropyl ether isopropyl ether and the sodium salt of benzyl alcohol

An aromatic hydrocarbon yields a single mononitro derivative. The hydrocarbon is 1. 3. 5. ethylbenzene propylbenzene p-xylene 2. 4. o-xylene naphthalene

38. Which is the best way to prepare meta-bromoaniline? 1. Phe-NH2 2. Phe-H 3. 4. 5.

H2SO 4 Br2 H3O+

Br2

HNO3
Br2

Sn HCl
H3O+

(CH3CO)2O Phe-NO2

Phe-NO2
Phe-NO2

HNO3 H2SO4
H2SO 4

(NH4)2S
NaOH

NaNO2 HBr
NaBr fuse

CuBr
Sn HCl

Sn / HCl

39.

Which is the principal product when benzaldehyde is allowed to react with propionaldehyde in the presence of dilute aqueous sodium hydroxide at room temperature? 1.
OH O CH C O CH2CH3

2.

CH C CH3

CHO

O C CH2CH3

3.

4.

CH CH CH2 CHO

40.

Which does NOT represent a Diels-Alder type of reaction?

O
O

1.
+ O O O

2.
+ O

3. 5.

CH2=CHCH=CH2 + CH2=CHCOOH

4. CH3COCH3 + CH3CH=CHCHO

+ H2C

CH CHO

41.

Which statement about the aldol condensation is correct? 1. 2. 3. 4. A Lewis acid is commonly used as a catalyst. The initial step is probably the formation of a carbanion. A Lewis base is employed to induce carbocation formation. The carbon chain is lengthened through the elimination of 1 mole of water.

42.

Which is the strongest acid in water? 1. 3. 5. Phenol 4-aminophenol hydroquinone 2. 4. 3-nitrophenol 4-nitrophenol

43.

The most direct malonic ester synthesis of 3-phenylpropanoic acid would involve the use of 1. 3. 5. C6H5CH2CH2CH2Cl C6H5CH2Cl ClCH2COOH 2. 4. C6H5CH2CH2Cl C6H5Cl

44.

A compound gives a positive test with I2/NaOH and is extracted from benzene by saturated NaHSO3. It may be 1. 3. 5. CH3(CH2)4CHO CH3CH2COCH2CH3 CH3(CH2)3)CHOHCH3 2. 4. CH3(CH2)3COCH3 CH3(CH2)4CH2OH

45.

Which is an L-sugar that on oxidation gives an optically inactive dibasic acid (2 COOH groups)? 1.
H HO HO CHO OH H H CH2OH

2.
H HO H

CHO OH H OH CH2OH

3.
H H H

CHO OH OH OH CH2OH

4.
HO H HO

CHO H OH H CH2OH

5.
HO H H

CHO H OH OH CH2OH

46.

Select the final product from this sequence of reactions.

NaOH CCl3 H2O

H3O+

HNO3 H2SO 4

Sn HCl
COOH

HNO2

OH

HO

1.
CH2 N N

2.
N N OH

3.
NO 2

C O

4.

COOH

OH

5.

HOOC

OH

47.

In the reaction below, the product would be

OH CHO + HCN C H CN

1. 3. 5. 48.

a racemate. a meso compound. unresolvable.

2. 4.

optically active. a mixture of diastereomers.

A group which deactivates the benzene ring towards EAS but which directs the incoming group principally to the ortho and para positions is 1. 3. 5. -NH2 -NO2 -NHCOCH3 2. 4. -Cl -C2H5

49. What is true for the equilibrium reaction

O CH3 C OH
1. 2. 3. 4. 5.

O CH3 OH cat. CH3 C O CH2 CH3 + H2O

The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of the ester at equilibrium. Removal of water will increase the amount of ester at equilibrium. Addition of CH3COOCH3 will cause the formation of equal an equal number of moles of water. Application of pressure increases the amount of ester at equilibrium. Changing the catalyst will affect the position of the equilibrium.

50. Which reagent would bring about this transformation?

RCOOH
1. 3. 5. Sn and HCl H2 and Pt Na and alcohol

RCH 2OH
2. 4. Zn and HCl LiAlH4 and ether

51. The reaction between carbon dioxide and a Grignard reagent will yield 1. 3. 5. an alkane. an alcohol. a carboxylic acid. 2. 4. an alkylmagnesium halide. magnesium carbonate.

52. Which is a practical method for the preparation of iodobenzene? 1. 2. 3. 4. 5. iodine + benzene + iron iodine + benzene + UV light potassium iodide + chlorobenzene sodium hypoiodite + benzamide potassium iodide + benzenediazonium ion

53. Which reaction sequence would be best to prepare 3-chloroaniline from benzene? 1. 3. 5. chlorination, nitration, reduction 2. nitration, chlorination, reduction nitration, reduction, chlorination 4. nitration, chlorination nitration, reduction, acetylation, chlorination, hydrolysis

54. The catalyst used in the halogenation of benzene is 1. 3. 5. a proton donor. a Lewis base a proton acceptor 2. 4. an electron donor. a Lewis acid

55. The reaction of Br2/FeBr3 with benzene to form bromobenzene is know as 1. 3. 5. free radical substitution electrophilic substitution elimination 2. 4. nucleophilic substitution ionic addition

56. Which reagent will lengthen the carbon chain by two carbons in one step when reacted with an organolithium reagent? 1. 3. 5. acetic acid iodomethane ethanol 2. 4. formaldehyde ethylene oxide

57. Which aromatic compound behaves most like benzoic acid when it undergoes reaction with concentrated nitric acid and sulfuric acid? 1. 3. 5. Phenol Phenyl methyl ketone Toluene 2. 4. Chlorobenzene Benzene

58. An explanation of the addition of sodium bisulfite to heptanal and 2-heptanone but not to 3heptanone is 1. 3. 5. steric inhibition of resonance. 2. steric hinderance. steric inhibition of solvation. 4. differences in resonance effects. the lower dipole moment of 3-heptanone.

59. Which will undergo a Friedel-Crafts alkylation reaction?

CH3 CH3 CH2 OH C O OH

NO 2 A B C D

1. 3. 5.

a, b, c b and d c and d

2. 4.

a and c a and b

60. The reaction of diethylmalonate with sodium ethoxide produces ethanol and a 1. 3. 5. free radical molecular species carboxylate ion 2. 4. carbocation carbanion

61. The principal product of the reaction between methyl butanoate and 2 moles of CH3MgBr after hydrolysis is 1. 3. 5. C3H7COCH3 C3H7CHOHCH3 C3H7CH2OH 2. 4. C3H7C(OH)(CH3)2 C3H7COCH(CH3)2

62. Which reaction sequence would be best to prepare 1,4-diaminobenzene from benzene 1. 2. 3. 4. 5. nitration, sulfonation, nitration, hydrolysis, reduction nitration, reduction, nitration, reduction nitration, reduction, acetylation, nitration, reduction nitration, reduction, acetylation, nitration, hydrolysis, reduction nitration, reduction
Cl

63. The correct name for

is

Cl

1. 3. 5.

7,9-dichloronaphthalene 2,4- dichloronaphthalene 6,8- dichloronaphthalene

2. 4.

3,5- dichloronaphthalene 1,3- dichloronaphthalene

64. Which of the following would react most rapidly with sodium ethoxide to produce an ether? 1. 3. 5. chlorobenzene p-nitrochlorobenzene m-chlorotoluene 2. 4.
p-nitrotoluene m-(chloromethyl)-toluene

65. Select the final product from this sequence of reactions.

Acetoacetic ester
O H3C C CH3 C COOC 2H5

NaOEt

CH3I

NaOEt

CH3CH2CH2Br

1.

2.
H3C

CH3 C CH2COOC 2H5

CH2CH2CH3

CH2CH2CH3

3.

H3C

CH2COOC 2H5

4.
CH3CO

CH3 C CH3 CH2COOC 2H5

CH2CH2CH3

5.

CH3 CH3CO C CH3 CH2CH2CH3