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1. Absorption of what type electromagnetic radiation results in transitions among allowed vibrational motions?. A. B. C. D. E. 2. X-rays radio waves microwaves ultraviolet light infrared light 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. B. C. D. E. a meso dibromide a mixture of enantiomeric dibromides which is optically active a mixture of enantiomeric dibromides which is optically inactive (Z)-3,4-dibromo-3-hexene (E)-3,4-dibromo-3-hexene Page 1 4. Which of the following best describes the carbon-chlorine bond of an alkyl chloride? A. B. C. D. E. 5. nonpolar; no dipole polar; δ+ at carbon and δ- at chlorine polar; δ- at carbon and δ+ at chlorine ionic none of the above An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is: A. B. C. D. E. 6. benzoic acid 2,2-dimethylpropanoic acid propanoic acid 4-oxocyclohexanecarboxylic acid 2-methylbutanoic acid Choose the correct hybridization for the atom indicated in the molecule below. CH 3 C C C H H CH 3 A. sp B. sp2 sp3 C. D. none of the above Page 2 7. Classify the reaction below as an oxidation, a reduction, or neither. (CH3)2CHCH2OH A. 8. oxidation B. (CH3)2CHCHO reduction C. neither 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. B. C. D. E. 9. ----------> The activation energy for the abstraction of a deuterium atom is higher. The activation energy for the abstraction of a hydrogen atom is higher. The activation energies fro abstraction are identical since H and D are isotopes. There is no activation energy for abstraction of either a hydrogen or a deuterium atom. Not enough information to decide. The reaction of LDA with acetophenone produces: A. B. C. D. E. an enol. an enolate. an ylide. alkylation. halogenation. Page 3 Which of the following is a secondary alkyl halide? A. B. C. D. E. 11. The correct priority of functional groups in IUPAC nomenclature is: A. B. C. D. E. 12. methyl bromide ethyl iodide t-butyl iodide isopropyl bromide isobutyl chloride ester > amide > ketone > acid. ketone > acid > ester > amide. acid > ester > amide > ketone. amide > acid > ester > ketone. amide > ester > acid > ketone. Which of the following choices represent(s)a pair of resonance structures? A. O CH 3 CH 2 B. C H , CH 3CH CH : , CH3CH + OCH 3 : OCH 3 : + CH 3 CH OH C. H H : C C N : 10. H D. E. , - :C C H Both a and c Both b and c Page 4 N: 13. 14. Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) __________ mechanism. A. SN1 B. SN2 C. D. E. E1 E2 ring opening 1-Methylcyclopentanol is classified as _____________________. A. C. 15. a primary alcohol a tertiary alcohol B. D. a secondary alcohol none of the above An ylide is a molecule that can be described as a: A. B. C. D. E. carbanion bound to a carbocation bound to carbocation bound to carbocation bound to carbanion bound to a negatively charged heteroatom. a negatively charged heteroatom. a carbanion. a diazonium ion. positively charged heteroatom. Page 5 16. Rank the free radicals (I-III) shown below in order of decreasing stability (ie, from most stable to least stable). ⋅ CH2CH 2CH(CH3)2 CH3CH2˙ C(CH3)2 CH3˙ CHCH(CH3)2 A. B. C. D. E. 17. II III I > III > II II > III > I I > II > III II > I > III III > II > I Secondary amines react with the nitrosonium ion to generate: A. B. C. D. E. 18. I diazonium salts N-nitrosoamines oximes imines none of the above The aldol condensation is: A. B. C. D. E. an irreversible reaction. an equilibrium reaction. a tautomerization. an isomerization. a type of esterification. Page 6 19. The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce an amide is: A. B. C. an acid-base reaction nucleophilic attack on the carbonyl carbon loss of H2O D. loss of CO2 loss of N2 E. 20. Which compound would be expected to show intense IR absorption at 1640 cm-1? A. C. 21. 1-hexene CH3CH2CH2OH B. D. 2-methylheptane CH3CH2COCH3 Which compound would be expected to show intense IR absorption at 3363, 3185, 1660 cm-1? A. CH3CH2CH2OH B. (CH3)2CHNH2 C. CH3CH2CONH2 D. 1-butene Page 7 22. When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is: A. B. C. D. E. 23. chiral achiral racemic optically active none of the above Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? CH3 Cl A. B. C. 24. E Z neither E nor Z How many distinct nodal planes which are perpendicular to the molecular plane are present in the π 5* orbital of benzene? A. 0 B. 1 C. 2 Page 8 D. 4 E. 5 25. In trans-4-hepten-2-yne the shortest carbon-carbon bond is between carbons ________________________. A. 26. B. 3 and 4 C. 4 and 5 D. 5 and 6 E. 6 and 7 Using Saytzeff's rule, choose the most stable alkene among the following. A. B. C. D. 27. 2 and 3 1-hexene (E)-2-hexene (Z)-2-hexene They are all of equal stability according to Saytzeff's rule. Which of the following describes a Rosenmund reduction? A. B. hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst reaction of a primary alcohol with Na2Cr2O7 C. D. reaction of a ketone with ozone treatment of an aldehyde with Sia2BH E. none of the above Page 9 28. Which of the following statements correctly describes the contribution of ∆S° to ∆G°? A. B. C. D. E. 29. ∆G° at low ∆G° at high ∆G° in exothermic ∆G° in endothermic contribution to The hydrolysis of esters in base is called: A. B. C. D. E. 30. The entropy term makes a greater contribution to temperatures. The entropy term makes a greater contribution to temperatures. The entropy term makes a greater contribution to reactions. The entropy term makes a greater contribution to reactions. The entropy term always makes a more significant ∆G° than does the enthalpy term. the Fischer esterification. the Hunsdiecker reaction. the Dieckmann condensation. transesterification. saponification. 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. B. C. D. propanoic acid phenylacetic acid acetic acid (CH3)3CCO2H E. CH3(CH2)14CO2H Page 10 31. In the mass spectrum of isobutylbenzene, the base peak occurs at m/z: A. 32. 33. 134 B. 133 C. 119 D. 105 E. 91 Which compound will show an intense peak in the mass spectrum at m/z 58? A. CH3COCH2CH2CH3 B. (CH3)2CHCOCH3 C. CH3CH2COCH2CH3 D. (CH3)3CCHO E. (CH3)3CCOCH3 What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed α-bromination of a ketone? A. B. C. D. E. an enolate a Grignard reagent an acetylide a carbocation an enol Page 11 34. 35. The conjugate acid of ammonia, NH3, is: A. NH2- B. NH2OH C. NH4+ D. none of the above What is the product when cyclopentene is treated with Br2/H2O? A. C. 36. cis-2-bromocyclopentanol cis-1,2-dibromocyclopentane B. D. trans-2-bromocyclopentanol trans-1,2-dibromocyclopentane The Hunsdiecker reaction converts silver n-butanoate into: A. B. C. D. E. 1-bromobutane 1-bromopropane 2-bromobutane 2-bromopropane ethyl bromide Page 12 37. Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)? I. II. III. IV. V. A. B. C. D. E. 38. II and IV III and V I, IV, and V I only III, IV, and V An _______ molecular ion peak usually indicates the presence of an odd number of nitrogen atoms in the molecule. A. 39. Rate = k[base] Rate = k[base][RX] Rate = k[RX] The reactions occur in two distinct steps. Rearrangements are sometimes seen. even B. odd C. intense D. avsent Which functional groups below indicate the presence of two atoms connected by a triple bond? A. B. C. D. E. F. ether alkyne nitrile alkene both b and c none of the above Page 13 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. B. C. D. 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. C. E. 42. the peaks at m/z 103 and m/z 104 have equivalent intensities the peak at m/z 103 has an intensity which is 4 times that of the m/z 104 peak the peak at m/z 103 has an intensity which is 1/4 the intensity of the peak at m/z 104 none of the above 1-chloropentane 3-chloropentane 1-chloro-3-methylbutane B. D. 2-chloropentane 1-chloro-2-methylbutane When (R)-2-butanol is treated with TsCl in pyridine, the product formed is: A. B. C. D. E. an achial compound. a mixture of diastereomers. a racemic mixture. a single enantiomer. none of the above. Page 14 43. What is the approximate chemical shift of an alkynyl carbon in 13C NMR spectroscopy? A. 44. B. 30 ppm C. 70 ppm D. 120 ppm E. 200 ppm How many distinct p orbitals exist in the second electron shell, where n=2? A. 45. 10 ppm 0 B. 1 C. 2 D. 3 E. 4 Which of the following additions to alkenes occur(s) specifically in a syn fashion? A. B. dihydroxylation using OsO4, H2O2 addition of H2 C. D. E. F. G. hydroboration addition of Hcl both a and b a, b, and c none of the above Page 15 46. In the boat conformation of cyclohexane, the "flagpole" are located: A. B. C. D. E. 47. on the same carbon. on adjacent carbons. on C-1 and C-3. on C-1 and C-4. none of the above Methylamine reacts with acetophenone to yield the: A. B. C. D. E. 48. iminium salt. imine. acetal. amide enamine. The protons marked Ha and Hb in the molecule below are _____________. Hb Ha CH3CH2 OH A. B. C. D. E. chemically equivalent enantitopic diastereotopic endotopic none of the above Page 16 49. Which of the following amines can be resolved into enantiomers? A. B. C. D. E. 50. Which of the following best describes DDT? A. B. C. D. E. 51. trimethylamine 3-pentanamine 2-pentanamine dimethylammonium chloride 4-(dimethylamino)pyridine a a a a a chlorocarbon used to decaffeinate coffee beans polybrominated organic compound used as a herbicide Freon used as a foaming agent mixed alkyl halide used as an anesthetic polychlorinated organic compound used as an insecticide In nucleophilic acyl substitution,: A. B. C. D. E. protonation of the the carbonyl is followed immediately by loss of the leaving group. loss of the leaving group is followed by rearrangement of the carbocation. addition to the carbonyl by a nucleophile is followed by loss of the leaving group. ester hydrolysis is followed by deprotonation. an SN2 reaction occurs. Page 17 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. B. C. D. E. 53. + B + C + C + B + C only The reaction of PhMgBr with CH3COCH2CH3 gives: A. B. C. D. 54. A A B A A an achiral product a mixture of diastereomers. the racemate of a chiral product. a single enantiomer. The nitration of anisole: A. B. C. D. E. proceeds more rapidly than the nitration of benzene and yields predominantly the meta product. proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products. proceeds more slowly than the nitration of benzene and yields predominantly the meta product. proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products. proceeds at the same rate as the nitration of benzene and yields predominantly the meta product. Page 18 55. The relationship between ketones and their corresponding enols is one of: A. B. C. D. E. 56. isomers. stereoisomers. enantiomers. diastereomers. tautomers. Which of the following could result from the dehydration of an aldol? A. B. C. D. E. 57. 4-methyl-3-penten-2-one 4-methyl-4-penten-2-one 4-methyl-5-hexen-2-one 4-methyl-4-hexen-2-one 3-methyl-4-penten-2-one Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? CH3 CH 3 C C H A. Br E B. Z C. Page 19 neither E nor Z 58. Which of the following molecules is chiral? A. B. C. D. E. 59. Which of the following compounds has the most signals in the noise-decoupled 13C NMR spectrum? A. B. C. D. E. 60. 2,3-pentadiene 1,2-pentadiene 2-methyl-2,3-pentadiene 2-chloro-4-methyl-2,3-pentadiene none of the above molecules is chiral o-dibromobenzene m-dibromobenzene p-dibromobenzene 1,3,5-tribromobenzene 1,2,3,4-tetrabromobenzene In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a: A. B. C. D. E. 1,2-fashion. 1,3-fashion. 1,4-fashion. 1,5-fashion. Diels-Alder reaction. Page 20 61. If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain? A. n B. n+2 n-2 C. D. E. F. 62. 2n+2 2n-2 Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane? A. B. C. D. E. 63. 2n sodium sodium sodium sodium both a (R)-2-butoxide + iodoethane (S)-2-butoxide + iodoethane ethoxide + (R)-2-iodobutane ethoxide + (S)-2-iodobutane and d would work equally well Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways? A. SN1 B. SN2 C. D. E. E1 E2 none of the above Page 21 64. 65. Which of the following is not a possible termination step in the free radical chlorination of methane? A. ·CH3 + Cl2 -------> CH3Cl + B. ·CH3 + Cl· -------> CH3Cl C. ·CH3 + ·CH3 -------> CH3CH3 D. ·CH3 + wall -------> CH3-wall E. Cl· + wall -------> Cl-wall Cl· Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? OCH 3 OH Br A. B. C. 66. E Z neither E nor Z Which of the following species is the least nucleophilic? A. (CH3)3CO- B. H2O C. (CH3)3N D. BF3 E. CN- Page 22 67. What type of orbital do the lone pair electrons on oxygen occupy in ethanol? A. 68. C. p D. sp E. sp2 F. sp3 Which of the halogens below undergoes free radical halogenation with ethane most rapidly? A. 69. B. fluorine B. chlorine C. iodine D. bromine E. pyridine In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because: A. B. C. D. E. it donates electron density to the ring by induction and destabilizes the meta sigma complex. it donates electron density to the ring by resonance and stabilizes the ortho, para sigma complex. it donates electron density to the ring by induction and stabilizes the ortho, para sigma complex. it donates electron density to the ring by resonance and destabilizes the meta sigma complex. it withdraws electron density from the ring by induction and destabilizes the meta sigma complex. Page 23 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. B. C. D. E. 71. Which of the following is not a fused-ring heterocycle? A. B. C. D. E. 72. 0 1 2 3 none of the above purine pyrimidine benzofuran indole quinoline Which of the following is a secondary amine? A. B. C. D. E. cyclohexylamine 3-pentanamine methylamine N,N-dimethylaniline N-ethyl-1-propanamine Page 24 73. Which of the following statements is/are true? A. B. C. D. E. 74. hydrolysis. DIBAH reacts with acid chlorides to yield primary alcohols after hydrolysis. Both a and b. Both b and c. What descriptive term is applied to the type of diene represented by 1,5-octadiene? A. B. C. D. E. 75. Two equivalents of Grignard reagent react with acid chlorides to yield tertiary alcohols after hydrolysis. LiAlH4 reacts with acid chlorides to yield secondary alcohols after conjugated diene cumulated diene isolated diene alkynyl diene none of the above The chemical shifts for protons α to a carbonyl group: A. B. C. D. E. are similar for all acid derivatives. are farthest downfield for carboxylic acids. are farther downfield than those α to a nitrile. fall between δ 3.1 and δ 4.2. fall between δ 1.3 and δ 1.8. Page 25 76. The strongest dichlorobutanoic acid is: A. B. C. D. E. 77. acid acid acid acid acid Which of the functional groups below contain a hydroxyl group as a part of their structure? A. B. C. D. E. F. G. 78. 2,2-dichlorobutanoic 2,3-dichlorobutanoic 3,3-dichlorobutanoic 3,4-dichlorobutanoic 4,4-dichlorobutanoic aldehyde alcohol carboxylic acid amine a, b, and c only b and c only all of the above In the carbon NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring? A. B. C. D. E. -10.0-0.0 ppm 40.0-60.0 ppm 80.0-100.0 ppm 120.0-150.0 ppm 200.0-220.0 ppm Page 26 79. Choose the correct hybridization for the atom indicated in the molecule below. CH3CH2CH2CH3 A. sp B. sp2 sp3 C. D. 80. none of the above Which compound would show a larger than usual M+2 peak? A. CH3CH2CN B. CH3CH2SCH3 C. Page 27 CH3CH2CO2H D. CH3(CH2)2CH3 Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1 Chapter/ Question 11-54 7-62 8-50 6-1 20-50 2-26 10-1 4-41 22-60 6-13 21-52 1-16 13-32 9-14 22-32 4-45 19-45 22-23 20-30 11-49 11-19 6-33 7-57 16-6 14-14 7-32 18-32 4-16 21-18 20-49 16-53 18-14 22-12 1-26 8-62 20-38 6-49 11-43 2-53 11-50 7-53 10-26 14-18 1-5 8-60 3-54 22-20 12-13 19-12 6-12 21-9 (-,b,-) (-,e,-) (-,a,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,c,-) (-,a,-) (-,a,-) (-,a,-) (-,b,-) (-,b,-) (-,a,-) (-,a,-) (-,a,-) (-,b,-) (-,b,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,a,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,b,-) (-,b,-) (-,b,-) (-,c,-) (-,b,-) (-,a,-) (-,a,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,a,-) (-,a,-) (-,e,-) (-,a,-) (-,c,-) (-,b,-) (-,b,-) (-,b,-) Test Question 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 Correct Answer E B C B D B A A B D C E B C E B B B A A C B C C A B A B E D E A E C B B E B E C C D C D F D B B C E C Page 1 Answer Sheet for Test “TestFinal-360-1996-PracMicroo”, 9/1/1 Chapter/ Question 20-53 10-46 17-10 22-4 22-25 7-20 15-6 16-52 22-44 3-3 13-20 7-54 4-7 7-56 6-20 9-4 4-43 17-8 15-13 16-60 19-11 21-27 15-8 21-7 20-47 2-59 16-50 2-20 11-17 (-,a,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,b,-) (-,b,-) (-,a,-) (-,e,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,a,-) (-,b,-) (-,b,-) (-,a,-) (-,b,-) (-,a,-) (-,a,-) Test Question 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 Correct Answer C C B E A A A B C E A D A A D F A B D B E A C A A F D C B Page 2 Statistics for Test “TestFinal-360-1996-PracMicroo”. Total questions: 80 Key Word Total Difficulty Level Total Question Type Total None None a) Easy b) Mod c) Diff d) e) Mod f) Diff Free format True or False Multiple choice Matching 80 2 28 44 3 0 3 0 0 0 80 0