1. Absorption of what type electromagnetic radiation ...web.mnstate.edu/jasperse/Chem360/Practice...

1. Absorption of what type electromagnetic radiation results in transitions among allowed vibrational motions?.

A. X-raysB. radio wavesC. microwavesD. ultraviolet lightE. infrared light

2. Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-2-heptene.

A. H2SO4, heat B. 1. Br2, h

2. NaOH

C. 1. Br2, h

2. NEt3

D. 1. H2O, H+

2. H2SO4,

heat

3. Addition of Br2 to (Z)-3-hexene produces ____________________.

A. a meso dibromideB. a mixture of enantiomeric dibromides which is optically activeC. a mixture of enantiomeric dibromides which is optically inactiveD. (Z)-3,4-dibromo-3-hexeneE. (E)-3,4-dibromo-3-hexene

4. Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

A. nonpolar; no dipoleB. polar; δ+ at carbon and δ- at chlorineC. polar; δ- at carbon and δ+ at chlorineD. ionicE. none of the above

5. An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is:

A. benzoic acidB. 2,2-dimethylpropanoic acidC. propanoic acidD. 4-oxocyclohexanecarboxylic acidE. 2-methylbutanoic acid

6. Choose the correct hybridization for the atom indicated in the molecule below.

HH

CH 3

C

CH 3

C C

A. sp

B. sp2

C. sp3

D. none of the above

7. Classify the reaction below as an oxidation, a reduction, or neither.

(CH3)2CHCH2OH ----------> (CH3)2CHCHO

A. oxidation B. reduction C. neither

8. How does the activation energy for the abstraction of a deuterium atom compare to the activation energy for the abstraction of a hydrogen atom?

A. The activation energy for the abstraction of a deuterium atom is higher.

B. The activation energy for the abstraction of a hydrogen atom is higher.

C. The activation energies fro abstraction are identical since H and D are isotopes.

D. There is no activation energy for abstraction of either a hydrogen or a deuterium atom.

E. Not enough information to decide.

9. The reaction of LDA with acetophenone produces:

A. an enol.B. an enolate.C. an ylide.D. alkylation.E. halogenation.

10. Which of the following is a secondary alkyl halide?

A. methyl bromideB. ethyl iodideC. t-butyl iodideD. isopropyl bromideE. isobutyl chloride

11. The correct priority of functional groups in IUPAC nomenclature is:

A. ester > amide > ketone > acid.B. ketone > acid > ester > amide.C. acid > ester > amide > ketone.D. amide > acid > ester > ketone.E. amide > ester > acid > ketone.

12. Which of the following choices represent(s)a pair of resonance structures?

A.

CH

OH

C

O

HCH3CH 2 , CH3CH

B.

CH3 CH OCH 3 CH3CH OCH3

+ :: ,

+

:

C.

H

C C N

H

:C C

H

N:

H

:

:- , -

D. Both a and cE. Both b and c

13. Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) __________ mechanism.

A. SN1

B. SN2

C. E1D. E2E. ring opening

14. 1-Methylcyclopentanol is classified as _____________________.

A. a primary alcohol B. a secondary alcoholC. a tertiary alcohol D. none of the above

15. An ylide is a molecule that can be described as a:

A. carbanion bound to a negatively charged heteroatom.B. carbocation bound to a negatively charged heteroatom.C. carbocation bound to a carbanion.D. carbocation bound to a diazonium ion.E. carbanion bound to a positively charged heteroatom.

16. Rank the free radicals (I-III) shown below in order of decreasing stability (ie, from most stable to least stable).

⋅ CH2CH2CH(CH3)2 I CH3CH2˙ C (CH3)2 II

CH3˙ C HCH(CH3)2 III

A. I > III > IIB. II > III > IC. I > II > IIID. II > I > IIIE. III > II > I

17. Secondary amines react with the nitrosonium ion to generate:

A. diazonium saltsB. N-nitrosoaminesC. oximesD. iminesE. none of the above

18. The aldol condensation is:

A. an irreversible reaction.B. an equilibrium reaction.C. a tautomerization.D. an isomerization.E. a type of esterification.

19. The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce an amide is:

A. an acid-base reactionB. nucleophilic attack on the carbonyl carbonC. loss of H2O

D. loss of CO2E. loss of N2

20. Which compound would be expected to show intense IR absorption at 1640 cm-1?

A. 1-hexene B. 2-methylheptaneC. CH3CH2CH2OH D. CH3CH2COCH3

21. Which compound would be expected to show intense IR absorption at 3363, 3185,

1660 cm-1?

A. CH3CH2CH2OH B. (CH3)2CHNH2C. CH3CH2CONH2 D. 1-butene

22. When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

A. chiralB. achiralC. racemicD. optically activeE. none of the above

23. Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

Cl

CH3

A. EB. ZC. neither E nor Z

24. How many distinct nodal planes which are perpendicular to the molecular plane

are present in the π5* orbital of benzene?

A. 0 B. 1 C. 2 D. 4 E. 5

25. In trans-4-hepten-2-yne the shortest carbon-carbon bond is between carbons ________________________.

A. 2 and 3 B. 3 and 4 C. 4 and 5 D. 5 and 6 E. 6 and 7

26. Using Saytzeff's rule, choose the most stable alkene among the following.

A. 1-hexeneB. (E)-2-hexeneC. (Z)-2-hexeneD. They are all of equal stability according to Saytzeff's rule.

27. Which of the following describes a Rosenmund reduction?

A. hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned

catalystB. reaction of a primary alcohol with Na2Cr2O7C. reaction of a ketone with ozoneD. treatment of an aldehyde with Sia2BH

E. none of the above

28. Which of the following statements correctly describes the contribution of ∆S° to ∆G°?

A. The entropy term makes a greater contribution to ∆G° at low temperatures.

B. The entropy term makes a greater contribution to ∆G° at high temperatures.

C. The entropy term makes a greater contribution to ∆G° in exothermic reactions.

D. The entropy term makes a greater contribution to ∆G° in endothermic reactions.

E. The entropy term always makes a more significant contribution to ∆G° than does the enthalpy term.

29. The hydrolysis of esters in base is called:

A. the Fischer esterification.B. the Hunsdiecker reaction.C. the Dieckmann condensation.D. transesterification.E. saponification.

30. An acid which could not be prepared by the reaction of an organic halide with cyanide ion followed by acid hydrolysis of the nitrile is:

A. propanoic acidB. phenylacetic acidC. acetic acidD. (CH3)3CCO2H

E. CH3(CH2)14CO2H

31. In the mass spectrum of isobutylbenzene, the base peak occurs at m/z:

A. 134 B. 133 C. 119 D. 105 E. 91

32. Which compound will show an intense peak in the mass spectrum at m/z 58?

A. CH3COCH2CH2CH3B. (CH3)2CHCOCH3C. CH3CH2COCH2CH3D. (CH3)3CCHO

E. (CH3)3CCOCH3

33. What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed α-bromination of a ketone?

A. an enolateB. a Grignard reagentC. an acetylideD. a carbocationE. an enol

34. The conjugate acid of ammonia, NH3, is:

A. NH2- B. NH2OH

C. NH4+ D. none of the above

35. What is the product when cyclopentene is treated with Br2/H2O?

A. cis-2-bromocyclopentanol B. trans-2-bromocyclopentanolC. cis-1,2-dibromocyclopentane D. trans-1,2-dibromocyclopentane

36. The Hunsdiecker reaction converts silver n-butanoate into:

A. 1-bromobutaneB. 1-bromopropaneC. 2-bromobutaneD. 2-bromopropaneE. ethyl bromide

37. Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?

I. Rate = k[base]II. Rate = k[base][RX]III. Rate = k[RX]IV. The reactions occur in two distinct steps.V. Rearrangements are sometimes seen.

A. II and IVB. III and VC. I, IV, and VD. I onlyE. III, IV, and V

38. An _______ molecular ion peak usually indicates the presence of an odd number of nitrogen atoms in the molecule.

A. even B. odd C. intense D. avsent

39. Which functional groups below indicate the presence of two atoms connected by a triple bond?

A. etherB. alkyneC. nitrileD. alkeneE. both b and cF. none of the above

40. The two most abundant isotopes of boron are 10B and 11B, with 11B being about 4 times more abundant. In the mass spectrum of trimethylborate [(CH3O)3B],

____________________________________.

A. the peaks at m/z 103 and m/z 104 have equivalent intensitiesB. the peak at m/z 103 has an intensity which is 4 times that of the

m/z 104 peakC. the peak at m/z 103 has an intensity which is 1/4 the intensity of

the peak at m/z 104D. none of the above

41. Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?

A. 1-chloropentane B. 2-chloropentaneC. 3-chloropentane D. 1-chloro-2-methylbutaneE. 1-chloro-3-methylbutane

42. When (R)-2-butanol is treated with TsCl in pyridine, the product formed is:

A. an achial compound.B. a mixture of diastereomers.C. a racemic mixture.D. a single enantiomer.E. none of the above.

43. What is the approximate chemical shift of an alkynyl carbon in 13C NMR spectroscopy?

A. 10 ppm B. 30 ppm C. 70 ppm D. 120 ppm E. 200 ppm

44. How many distinct p orbitals exist in the second electron shell, where n=2?

A. 0 B. 1 C. 2 D. 3 E. 4

45. Which of the following additions to alkenes occur(s) specifically in a syn fashion?

A. dihydroxylation using OsO4, H2O2B. addition of H2C. hydroborationD. addition of HclE. both a and bF. a, b, and cG. none of the above

46. In the boat conformation of cyclohexane, the "flagpole" are located:

A. on the same carbon.B. on adjacent carbons.C. on C-1 and C-3.D. on C-1 and C-4.E. none of the above

47. Methylamine reacts with acetophenone to yield the:

A. iminium salt.B. imine.C. acetal.D. amideE. enamine.

48. The protons marked Ha and Hb in the molecule below are _____________.

Hb Ha

CH3CH2 OH

A. chemically equivalentB. enantitopicC. diastereotopicD. endotopicE. none of the above

49. Which of the following amines can be resolved into enantiomers?

A. trimethylamineB. 3-pentanamineC. 2-pentanamineD. dimethylammonium chlorideE. 4-(dimethylamino)pyridine

50. Which of the following best describes DDT?

A. a chlorocarbon used to decaffeinate coffee beansB. a polybrominated organic compound used as a herbicideC. a Freon used as a foaming agentD. a mixed alkyl halide used as an anestheticE. a polychlorinated organic compound used as an insecticide

51. In nucleophilic acyl substitution,:

A. protonation of the the carbonyl is followed immediately by loss of the leaving group.

B. loss of the leaving group is followed by rearrangement of the carbocation.

C. addition to the carbonyl by a nucleophile is followed by loss of the leaving group.

D. ester hydrolysis is followed by deprotonation.E. an SN2 reaction occurs.

52. An ether solution of PhCO2H (A), PhNH2 (B), and PhCH3 (C) is extracted with

aqueous NaOH. The ether layer will contain what compound(s) after the extraction?

A. A + BB. A + CC. B + CD. A + B + CE. A only

53. The reaction of PhMgBr with CH3COCH2CH3 gives:

A. an achiral productB. a mixture of diastereomers.C. the racemate of a chiral product.D. a single enantiomer.

54. The nitration of anisole:

A. proceeds more rapidly than the nitration of benzene and yields predominantly the meta product.

B. proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products.

C. proceeds more slowly than the nitration of benzene and yields predominantly the meta product.

D. proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products.

E. proceeds at the same rate as the nitration of benzene and yields predominantly the meta product.

55. The relationship between ketones and their corresponding enols is one of:

A. isomers.B. stereoisomers.C. enantiomers.D. diastereomers.E. tautomers.

56. Which of the following could result from the dehydration of an aldol?

A. 4-methyl-3-penten-2-oneB. 4-methyl-4-penten-2-oneC. 4-methyl-5-hexen-2-oneD. 4-methyl-4-hexen-2-oneE. 3-methyl-4-penten-2-one


CH3

C C

CH3

H Br

A. E B. Z C. neither E nor Z

58. Which of the following molecules is chiral?

A. 2,3-pentadieneB. 1,2-pentadieneC. 2-methyl-2,3-pentadieneD. 2-chloro-4-methyl-2,3-pentadieneE. none of the above molecules is chiral

59. Which of the following compounds has the most signals in the noise-decoupled 13C NMR spectrum?

A. o-dibromobenzeneB. m-dibromobenzeneC. p-dibromobenzeneD. 1,3,5-tribromobenzeneE. 1,2,3,4-tetrabromobenzene

60. In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a:

A. 1,2-fashion.B. 1,3-fashion.C. 1,4-fashion.D. 1,5-fashion.E. Diels-Alder reaction.

61. If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?

A. n

B. n+2

C. n-2

D. 2n

E. 2n+2

F. 2n-2

62. Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?

A. sodium (R)-2-butoxide + iodoethaneB. sodium (S)-2-butoxide + iodoethaneC. sodium ethoxide + (R)-2-iodobutaneD. sodium ethoxide + (S)-2-iodobutaneE. both a and d would work equally well

63. Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

A. SN1

B. SN2

C. E1D. E2E. none of the above

64. Which of the following is not a possible termination step in the free radical chlorination of methane?

A. ·CH3 + Cl2 -------> CH3Cl + Cl·

B. ·CH3 + Cl· -------> CH3Cl

C. ·CH3 + ·CH3 -------> CH3CH3D. ·CH3 + wall -------> CH3-wall

E. Cl· + wall -------> Cl-wall


OH

OCH3

Br

A. EB. ZC. neither E nor Z

66. Which of the following species is the least nucleophilic?

A. (CH3)3CO-

B. H2O

C. (CH3)3N

D. BF3

E. CN-

67. What type of orbital do the lone pair electrons on oxygen occupy in ethanol?

A. B. C. p D. sp E. sp2 F. sp3

68. Which of the halogens below undergoes free radical halogenation with ethane most rapidly?

A. fluorine B. chlorine C. iodine D. bromine E. pyridine

69. In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because:

A. it donates electron density to the ring by induction and destabilizes the meta sigma complex.

B. it donates electron density to the ring by resonance and stabilizes the ortho, para sigma complex.

C. it donates electron density to the ring by induction and stabilizes the ortho, para sigma complex.

D. it donates electron density to the ring by resonance and destabilizes the meta sigma complex.

E. it withdraws electron density from the ring by induction and destabilizes the meta sigma complex.

70. How many nodes, other than the node coincident with the molecular plane, are found in the highest energy π MO of 1,3-butadiene?

A. 0B. 1C. 2D. 3E. none of the above

71. Which of the following is not a fused-ring heterocycle?

A. purineB. pyrimidineC. benzofuranD. indoleE. quinoline

72. Which of the following is a secondary amine?

A. cyclohexylamineB. 3-pentanamineC. methylamineD. N,N-dimethylanilineE. N-ethyl-1-propanamine

73. Which of the following statements is/are true?

A. Two equivalents of Grignard reagent react with acid chlorides to yield tertiary alcohols after hydrolysis.

B. LiAlH4 reacts with acid chlorides to yield secondary alcohols after

hydrolysis.C. DIBAH reacts with acid chlorides to yield primary alcohols after

hydrolysis.D. Both a and b.E. Both b and c.

74. What descriptive term is applied to the type of diene represented by 1,5-octadiene?

A. conjugated dieneB. cumulated dieneC. isolated dieneD. alkynyl dieneE. none of the above

75. The chemical shifts for protons α to a carbonyl group:

A. are similar for all acid derivatives.B. are farthest downfield for carboxylic acids.C. are farther downfield than those α to a nitrile.D. fall between δ 3.1 and δ 4.2.E. fall between δ 1.3 and δ 1.8.

76. The strongest dichlorobutanoic acid is:

A. 2,2-dichlorobutanoic acidB. 2,3-dichlorobutanoic acidC. 3,3-dichlorobutanoic acidD. 3,4-dichlorobutanoic acidE. 4,4-dichlorobutanoic acid

77. Which of the functional groups below contain a hydroxyl group as a part of their structure?

A. aldehydeB. alcoholC. carboxylic acidD. amineE. a, b, and c onlyF. b and c onlyG. all of the above

78. In the carbon NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring?

A. -10.0-0.0 ppmB. 40.0-60.0 ppmC. 80.0-100.0 ppmD. 120.0-150.0 ppmE. 200.0-220.0 ppm

79. Choose the correct hybridization for the atom indicated in the molecule below.

CH3CH2CH2CH3

A. sp

B. sp2

C. sp3

D. none of the above

80. Which compound would show a larger than usual M+2 peak?

A. CH3CH2CN B. CH3CH2SCH3 C. CH3CH2CO2H D. CH3(CH2)2CH3

Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1

Chapter/ Test CorrectQuestion Question Answer

11-54 (-,b,-) 1 E7-62 2 B8-50 (-,e,-) 3 C6-1 (-,a,-) 4 B20-50 (-,b,-) 5 D2-26 (-,b,-) 6 B10-1 (-,a,-) 7 A4-41 (-,b,-) 8 A22-60 (-,a,-) 9 B6-13 (-,b,-) 10 D21-52 (-,b,-) 11 C1-16 (-,c,-) 12 E13-32 (-,a,-) 13 B9-14 (-,a,-) 14 C22-32 (-,a,-) 15 E4-45 (-,b,-) 16 B19-45 (-,b,-) 17 B22-23 (-,a,-) 18 B20-30 (-,a,-) 19 A11-49 (-,a,-) 20 A11-19 (-,b,-) 21 C6-33 (-,b,-) 22 B7-57 (-,b,-) 23 C16-6 (-,b,-) 24 C14-14 (-,a,-) 25 A7-32 (-,b,-) 26 B18-32 (-,a,-) 27 A4-16 (-,b,-) 28 B21-18 (-,a,-) 29 E20-49 (-,b,-) 30 D16-53 (-,b,-) 31 E18-14 (-,b,-) 32 A22-12 (-,b,-) 33 E1-26 (-,b,-) 34 C8-62 35 B20-38 (-,c,-) 36 B6-49 (-,b,-) 37 E11-43 (-,a,-) 38 B2-53 (-,a,-) 39 E11-50 (-,b,-) 40 C7-53 (-,a,-) 41 C10-26 (-,b,-) 42 D14-18 (-,b,-) 43 C1-5 (-,a,-) 44 D8-60 (-,a,-) 45 F3-54 (-,e,-) 46 D22-20 (-,a,-) 47 B12-13 (-,c,-) 48 B19-12 (-,b,-) 49 C6-12 (-,b,-) 50 E21-9 (-,b,-) 51 C

Page 1

Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1

Chapter/ Test CorrectQuestion Question Answer

20-53 (-,a,-) 52 C10-46 (-,b,-) 53 C17-10 (-,b,-) 54 B22-4 (-,a,-) 55 E22-25 (-,b,-) 56 A7-20 (-,b,-) 57 A15-6 (-,b,-) 58 A16-52 (-,b,-) 59 B22-44 (-,a,-) 60 C3-3 (-,e,-) 61 E13-20 (-,b,-) 62 A7-54 (-,a,-) 63 D4-7 (-,b,-) 64 A7-56 (-,b,-) 65 A6-20 (-,b,-) 66 D9-4 (-,b,-) 67 F4-43 (-,a,-) 68 A17-8 (-,b,-) 69 B15-13 (-,b,-) 70 D16-60 (-,b,-) 71 B19-11 (-,a,-) 72 E21-27 (-,b,-) 73 A15-8 (-,a,-) 74 C21-7 (-,b,-) 75 A20-47 (-,b,-) 76 A2-59 (-,a,-) 77 F16-50 (-,b,-) 78 D2-20 (-,a,-) 79 C11-17 (-,a,-) 80 B

Page 2

Statistics for Test “TestFinal-360-1996-PracMicroo”. Total questions: 80

Key Word Total Difficulty Level Total Question Type Total

2None80None Free format 028a) Easy True or False 044b) Mod Multiple choice 803c) Diff Matching 00d) 3e) Mod 0f) Diff

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