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OrganicChemistry
INSTRUCTION:Selectthecorrectanswerforeachofthefollowing
sections.Markonlyoneanswerforeachitembyshadingthebox
correspondingtotheletterofyourchoiceontheanswersheet
provided.STRICTLYNOERASURESALLOWED.Usepencilno.1only.

1. Inthenucleophilicaromaticsubstitutionreactionofnitrobenzene,
whichofthefollowingdoesnotapply?
a. Itisatwostepbimoleculardisplacement
b. Electronwithdrawinggroupsincreasetherateof
reaction
c. Thetypeofhalidedoesnotaffectthereactionrate
d. Alargeisotopiceffectisobserved

2. ThedehydrationofalcoholinvolvesE1eliminationwiththe
formationofacarbonium(orcarbocation)ion.Thisoccursin:
a. Basicmedium
b. Stronglybasicmedium
c. Acidicmedium
d. pHisnotimportant

3. Forthechemicaltransformationofbenzamidetoaniline,the
reagents(s)neededis/are:
a. KMnO4
b. NaOH+Br2
c. NaNO2+H2SO4
d. Noneofthegivenanswers

4. Whydoelectronwithdrawingsubstitutentssuchasthehalogens
increasetheacidityofaceticacid?
a. Thehalogensstabilizethecarboxylateion
b. Thehalogensintensifythenegativechargeonthe
carboxylateion
c. Thehalogensdestabilizethecarboxylateion
d. Noneofthegivenanswers
PreparedbyJEPaa/forBSChemGraduate2006

5. Whichofthefollowingcompoundsformsthemoststable
carbocation?
a. Nitrobenzene
b. Aniline
c. Toluene
d. Benzaldehyde

6. Thepropersequenceofeventstoconvertbenzenetombromo
nitrobenzeis:
a. Simultaneousbrominationandnitration
b. Brominationfollowedbynitration
c. NitrationfollowedbyFriedelCraftsalkylationand
bromination
d. Nitrationfollowedbybromination

7. Thenitrationofbenzenedoesnotexhibitasignificantisotope
effectbecause:
a. ACHbondisbrokenattheratedeterminingstep
b. K1>K2
c. NoCHisbrokenattheratedeterminingstep
d. Noneofthegivenanswers

8. Whichofthefollowinggivesapositiveiodoformtest?
a. 3pentanone
b. Methanol
c. Ethanol
d. tertbutylalcohol

9. Whatwouldbetheproduct(s)ofthereactionofethylbromide
andsodiumtertbutoxide?
a. 2methylpropaneandethanol
b. 2methylpropeneandethanol
c. Ethyltertbutylether
d. Noneofthegivenanswers

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10. Predicttheorderofreactivitytowardsalkalinehydrolysisof(most
reactivefirst):
I.methylacetate,II.methylformate,III.methylpropionate
a. II>I>III
b. II>III>I
c. I>II>III
d. III>I>II

11. Thehydrolysisofethylbenzoatelabeledwith18O(CO18O)yields
thefollowing:
a. Phenollabeledwith18O
b. Ethanollabeledwith18O
c. Aceticacidlabeledwith18O
d. Benzoicacidlabeledwith18O

12. Nylon66isformedfromadipicacidandhexamethylenediamine
by:
a. Cationchainreactionpolymerization
b. Freeradicalchainreactionpolymerization
c. Stepreactionpolymerization
d. Anionchainreactionpolymerization
e. Noneofthese

13. ThereactivityoftheC=Ogroupinpropanalisprimarilydueto:
a. Abilityofoxygentoacquireelectrons
b. Inductiveeffectofneighboringgroups
c. PolarityoftheC=Ogroup
d. Noneofthese

14. Glycogenconsistsofmonomericunitsof:
a. Mannose
b. Galactose
c. Fructose
d. Sucrose
e. Glucose
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15. Whichcompounddoesnotcontainacarbonylgroup?
a. Ester
b. Ketone
c. Ether
d. Carboxylicacid

16. IntheClaisencondensationofCH3COOC2H5andO14C2H5ion,the
C14labelwillbedetectedinwhichproduct?
a. Ethylacetoacetate
b. Ethylacetate
c. Carbondioxide
d. Ethanol
e. Noneofthese

17. Whichofthefollowingcandisrupthydrophobicbondsin
proteins?
a. Dichloroaceticacid
b. Sodiumlaurylsulfate
c. Mercaptoethanol
d. Dioxane
e. Nocorrectanswer

18. AKjeldahlnitrogenanalysisof4.27mgofnitrobenzenerequired
5.35mLof0.0150NHCltoneutralizetheammoniaproduced.
Calculatethe%nitrogeninthecompound.
a. 26%
b. 1.3%
c. 13%
d. 2.6%
e. Noneofthegivenanswers

19. 2OHbutanereactswithHClinthepresenceofzincchlorideand
understrongheat.Thefinalproductofthereaction:
a. Hasaretentionofconfiguration
b. Isracemic

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c. Hasinversionofconfiguration
d. Noneofthechoices

20. ApolypeptidechainistreatedwithLiAlH4,thenhydrolyzed,2
amino1propanolseparatesout.TheCterminalaminoacidof
thepolypeptideis:
a. Alanine
b. Lysine
c. Praline
d. Noneofthegivenanswers

21. Catalyticcrackingofoildirectlyyields:
a. Alkenes
b. Antiknockcompounds
c. Gasoline
d. Allofthese

22. WhichofthefollowingcompoundsisthemostreactivebySN1
mechanism?
a. Isopropylchloride
b. nbutylchloride
c. npropylchloride
d. tertbutylchloride

23. Whichofthefollowingaremanmadepolymers?
a. Silk
b. Plastics
c. Lignin
d. Naturalrubber
e. Allarecorrectanswers

24. WhenCH3CO18OHwasmadetoreactwithmethanol,themethyl
acetatewasfoundtocontainonlyordinaryO.Whichbondswere
broken?
a. COHofacidandCOHofalcohol
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b. COHofacidandCOHofalcohol
c. COHofacidandCOHofalcohol
d. Noneofthese

25. Whatcarboxylicacidispreparedfrompbromotoluenebyfree
radicalhalogenationfollowedbynitrilesynthesis?
a. pbromophthalicacid
b. pbromobenzoicacid
c. pbromophenylaceticacid
d. Noneofthese

26. Intheconversionofacetylchloridetoacetamide,whatwouldbe
theeffectofelectronwithdrawingsubstitutentsonthe
tetrahedralintermediate?
a. Theystabilizethepartialchargeonoxygen
b. Theacylcompoundundergoesnucleophilicaddition
c. Theydestabilizethepartialchargeonoxygen
d. Noneofthegivenanswers

27. Whatisthesubstrateoftrypsin?
a. Coconutoil
b. Starch
c. Noneofthegivenanswers
d. Protein

28. Howmanyisomericdisubstitutionproductsaretheoretically
possibleuponthebrominationofbenzene?
a. 2
b. 4
c. 3
d. 6
e. Noneofthechoices

29. CleavageofisopropylphenyletherbyHBryields:
a. BenzeneandisopropylBr

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b. isopropylBrandphenol
c. bromobenzeneandisopropanol
d. noneofthesechoices

30. Themajorproductofdehydrohalogenationof5Cl2hepteneis:
a. 2,4heptadiene
b. Propanoicacidandbutenoicacid
c. 2,5heptadiene
d. Noneofthegivenchoices

31. Considerthechlorinationofmethaneinthepresenceoflight.
Oxygenactsasaninhibitorbecauseitbreaksthechainreaction
by:
a. Reactingwithmethane
b. Reactingwithchlorineatom
c. ReactingwithCl2
d. Noneofthegivenanswers

32. Oxidationofhexanolbyacidicdichromateyields:
a. Hexanal
b. 2hexanone
c. Hexanoicacid
d. Noneofthegivenanswers

33. Predictthemajorproductofdehydrationof3OH3,4
dimethylhexane:
a. 3,4dimethyl2hexene
b. 2,4dimethyl1hexene
c. 3,4dimethyl1hexene
d. 3,4dimethyl3hexene

34. TheIRspectrumofthechairformofcyclohexanediffersfromthat
oftheboatforminthefollowingaspect(s):
a. CHstretchingbandsareonsamewavenumber
PreparedbyJEPaa/forBSChemGraduate2006

b. CHstretchingbandfortheboatformisathigher
wavenumber
c. CHstretchingbandforchairformisathigher
wavenumber
d. Noneofthegivenanswers

35. Enantiomersofmethylethylbutylaminearedifficulttoisolate
becauseof:
a. Conformation
b. Rotation
c. Inversion
d. Noneofthese

36. Asolutionofbromineincarbontetrachloridebecomescolorless
inthepresenceofethene.Theproductformedis:
a. Bromoethane
b. 1,2dibromoethane
c. 1,1,2,2tetrabromoethane
d. Noneofthese

37. 2OHbutanereactswithHClinthepresenceofzincchlorideand
understrongheat.Whatisthereactionmechanisminvolvedin
thisreaction?
a. E2
b. SN2
c. E1
d. SN1

38. Ozonolysisof2methyl1,3butadieneyields:
a. Aldehydeandacids
b. Acids
c. Aldehydes
d. Noneofthechoices

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39. Givetheproductofesterificationbetweenbenzoicacidand
ethanol.
a. Ethylbenzoate
b. Ethylbenzaldehyde
c. Benzylacetate
d. Noneofthegivenanswers

40. TheBataanNuclearPowerPlantisbeingproposedforconversion
toacombinedcyclepowerplantusingnaturalgasasfuel.Natural
gasconsistsof:
a. Butane
b. Methane
c. Ethane
d. Noneofthese

41. TheIRspectrumofadilutesolutionofethanolshowsanOH
stretchingbandat3640cm1.Thisbandbecomesbroaderand
shiftsto3350cm1astheethanolconcentrationisincrease.
Explainthisshift.
a. HbondingtothesecondoxygenstrengthenstheOH
bond
b. Theenergyofvibrationisincreasedastheethanol
concentrationisincreased
c. HbondingtothesecondoxygenweakenstheOHbond
d. Noneofthegivenanswers

42. TertiaryalcoholsreactwithHXviaSN2mechanism.Thefeature(s)
ofthisreactionis(are):
a. Itisacidcatalyzed
b. Rearrangementispossible
c. Acarboniumionisformed
d. Allofthegivenanswers

PreparedbyJEPaa/forBSChemGraduate2006

43. Inthehalogenationofalkanesatordinarytemperature,therate
ofabstractionofHfollowsthesequence3o>2o>1o.An
explanationforthistrendis:
a. Freeradicalfrom1oHismoststable
b. Energyofactivationislowestin3oH
c. Theprobabilityofcollisionisgreatestbetweenhalogen
atomand3oH
d. Thecollisionfrequencyisgreatestbetweenthe
halogenatomandalkanewith3oH

44. Citereason(s)whyquarternaryammoniumsalts(A)withfour
differentgroupsattachedtonitrogenhavebeenfoundtoexistas
configurationalenantiomerswhileenantiomersofsimpleamines
(B),alsowithfourdifferentgroupsattachedtothenitrogen,have
notbeenisolated.
a. Ahassp3orbitals
b. PositivechargeonquarternaryN
c. UnsharedpairofelectronsonN
d. RapidinversionaboutNinB
e. Noneofthegivenanswers

45. Whichofthefollowingcompoundsisthemostacidic?
a. Methylamine
b. Methane
c. Methylfluoride
d. Methylalcohol

46. Arrangethefollowinginorderofbasicity(mostbasicfirst):
I,methylfluoride;II,methylchloride;III,methylbromide;
IV,methyliodide.
a. I>II>III>IV
b. IV>III>II>I
c. I>III>II>IV
d. Noneofthegivenanswers

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47. Thecarbonatomsofacetylenecontainthefollowinghybrid
orbitals:
a. sp3
b. sp2
c. s
d. sp

48. Indehalogenationofalkyhalides,theorderofreactivityis3o>
2o>1o.Thismaybedueto:
a. GreaternumberofHavailableforattackbybase
b. Lowerenergyofactivation
c. Morestabletransitionstate
d. Allofthese

49. Whichofthefollowingexistsasapairofconformational
diastereomers?
a. trans1,3cyclohexanediol
b. cis1,2cyclohexanediol
c. trans1,2cyclohexanediol
d. cis1,3cyclohexanediol

50. Arrangethefollowingaliphaticacidsinorderofincreasingacidity:
I,formicacid;II,aceticacid;III,propionicacid;IV,chloroacetic
acid:
a. III,II,I,IV
b. I,II,III,IV
c. IV,III,II,I
d. IV,I,II,III
e. Nocorrectanswer

51. Givethereactionproductoftertpentylalcoholwithalkaline
KMnO4.
a. 3methyl2butanone
b. 3methyl1butanal
c. 3mehyl1butanoicacid
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d. Noreaction

52. WhichofthefollowinghalidesisthemostreactivebySN1
mechanism?
a. Benzylchloride
b. tertbutylchloride
c. Chloroethane
d. 2chloro2propane

53. WhichofthefollowingcompoundsisthemostreactivetowardsI2
bytheSN2reaction?
a. Ethylbromide
b. Isobutylbromide
c. tertbutylbromide
d. Methylbromide
e. Isopropylbromide

54. GivetheproductofthereactionofpropanalwithNaCNfollowed
byhydrolysiswithacid.
a. 2OH2methylpropanoicacid
b. Propanoicacid
c. 2OHbutanoicacid
d. Noneofthese

55. Arrangethefollowinginorderofincreasingreactivitytowardsa
hydroxylgroupviaSN2mechanism:I,1bromopentane;II,1
bromo2methylpentane;III,1bromo2,2dimethylpentane;IV,
1bromo3methylpentane;V,2bromopentane
a. III,II,IV,V,I
b. I,II,V,III,IV
c. I,V,IV,II,III
d. III,II,V,IV,I
e. Noneofthese

56. AdditionofHBrtopropyleneinthepresenceofperoxidesyields:

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a. Equalamountsofisopropylbromideandnpropyl
bromide
b. npropylbromide
c. Isopropylbromide
d. Noneofthegivenanswers

57. Whatchemicaltestswilldistinguish3chloropropenefromn
propylchloride?I,Br2inCCl4;II,KMnO4;III,CrO3;IV,H2SO4
a. I,II,IV
b. I,II,III
c. I,II,III,IV
d. I,III
e. Noneofthegivenanswers

58. Inthereactionof1naphtholwithphenyldiazochloride,the
phenyldiazoniumionwillbindtowhichcarbonatomofthe
naphthalenemoiety?
a. C7
b. C2
c. C5
d. C4
e. C8

59. Whatistheshapeofamethylradical?
a. Trigonal
b. Orthogonal
c. Pyramidal
d. Noneofthegivenchoices

60. Whatistheshapeofanethylenemolecule?
a. Linear
b. Trigonal
c. Tetrahedral
d. Pyramidal

PreparedbyJEPaa/forBSChemGraduate2006

61. Thealdolcondensationreactionoftwomolesofacetaldehyde
withabasecatalystyields:
a. 2OHbutanone
b. 3OHbutanal
c. 3OHbutanone
d. 2OHbutanal

62. Theisoelectricpointofserumalbuminis4.9.AtpH=7.0,which
ofthefollowingstatementswouldbetrue?
I,theproteinmovestothecathode
II,theproteinmovestotheanode
III,majorityofitsionizinggroupsarebasic
IV,majorityofitsionizinggroupsareacidic
a. I,IV
b. II,III
c. I,III
d. II,IV
e. Noneofthegivenanswers

63. Acidcatalyzedhydrolysisofethyleneoxideyields:
a. Ethyleneglycol
b. Ethanol
c. Carbondioxide
d. Noneofthese

64. Whatwouldbetheproductsofmildalkalinehydrolysisof1oleyl
2palmitoyl3laurylglycerol?
a. Glycerol,sodiumlinoleate,sodiumpalmitate,sodium
laurate
b. Glycerol,sodiumoleate,sodiumpalmitate,sodium
laurate
c. Glycerol,oleicacid,palmiticacid,lauricacid
d. Glycerol,linoleicacid,palmiticacid,lauricacid
e. Noneofthegivenanswers

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65. CompoundZformsaclearsolutionwithbenzenesulfonylchloride,
fromwhichaninsolublematerialseparatesoutuponacidification.
CompoundZis:
a. Ethylamine
b. Methylethylamine
c. Trimethylamine
d. Noneofthegivenanswers

66. BrominationofisobuteneunderUVlightat127oCyields:
a. EqualamountsoftertbutylBrandisobutylBr
b. Isobutylbromideastheprimaryproduct
c. Tertbutylbromideastheprimaryproduct
d. Noreaction

67. Hydrolysisoflauropalmitinyields:
a. Lauricacid,palmiticacidandglycerol
b. Onemoleculeeachoflauricacid,palmiticacid,and
glycerol
c. Lauricacidandpalmiticacid
d. Noneofthegivenanswers

68. Arrangethefollowingalcoholsinorderofreactivityinthe
esterificationofaceticacid(mostreactivefirst):
a. Methanol>npropyl=secbutyl>tertpentylalcohol
b. Methanol>npropyl>secbutyl>tertpentylalcohol
c. Tertpentylalcohol>secbutyl>npropyl>methyl
alcohol
d. Methanol=npropyl>secbutyl>tertpentylalcohol
e. Noneofthegivenanswers

69. Thebasicityofanilineisincreasedby:
a. COOH,halidegroups
b. Amino,methoxy,halidegroups
c. Amino,methyl,halidegroups
d. Noneofthese
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70. Arrangethefollowinginincreasingorderofdelocalizationof
electronsbyhyperconjugation(compoundswithgreatest
delocalizationofelectronsfirst):
a. tbutyl>isopropyl>ethyl>methyl
b. tbutyl>isopropyl>ethyl=methyl
c. methyl>ethyl>isopropyl>tbutyl
d. tbutyl=isopropyl>ethyl>methyl
e. Noneofthegivenanswers

71. Whichoftheindicatedbondshasthelowestbonddissociation
energy(D)?
a. C6H5H
b. C6H5CH2CH3
c. C6H5CH3
d. C6H5CH2H
e. AllhaveequalD

72. Aproductdevelopmentmanagerwantsalowmolecularweight
polystyreneproduct.Giventhechaintransferconstantsof
severalchaintransferagents,whichofthesewouldbethemost
effectivetouse?
a. Benzene;0.02
b. Ethylbenzene;0.70
c. Toluene;0.20
d. Isopropylbenzene;1.00

73. ThefollowingcompoundsareusedasLewisacidcatalystsin
organicreactionsexcept:
a. BF3
b. AlCl3
c. CH3MgBr
d. SnCl4

74. Thetotalnumberofpossiblestructurescorrespondingtothe
formulaC4H9Iis:

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a. 7
b. 5
c. 4
d. 6
e. Noneofthese

75. Byendgroupanalysis,thehydrolysisofonemoleculeof
completelymethylatedamylasegivesriseto:
a. EqualnumberoftetraOmethylDglucoseandtriO
methylDglucose
b. OnemoleculeoftetraOmethylDglucose
c. OnemoleculeoftriOmethylDglucose
d. Noneofthegivenanswers

76. Arrangethefollowinginorderofincreasingboilingpoint(lowest
boilingpointfirst):
I,butanal;II,butylalcohol;III,butanoicacid;IV,ethylether
a. I,IV,II,III
b. IV,II,I,III
c. IV,I,II,III
d. Noneofthegivenanswers

77. Theeaseofabstractionofhydrogenatomsfromalkylhalides
followsthetrend:tertiaryH>secondaryH>primaryH.This
maybedueto:
a. ChangeintheRsubstituents
b. LengthoftheRsubstituents
c. Differencesinactivationenergies
d. Noneofthegivenanswers

78. Examinethestructureofthefollowingpolymerandidentifythe
monomericunit:(CH2CCl2CH2CCl2)n
a. 1,1dichloroethene
b. Styrene
c. Vinylchloride
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d. Noneofthegivenanswers

79. Whatisthemonomercomprisingtheplexiglass?
a. Ethyleneglycol
b. Acrylonitrile
c. Methylmethacrylate
d. Adipicacid
e. Vinylacetate

80. Inthedehydrogenationof1pentene,platinum:
a. Lowerstheenergyofactivation
b. Changesthenetenergychangeofreaction
c. Shiftsthepositionofequilibrium
d. Allofthese

81. Alcoholscanbeproducedbyreactingalkeneswith
hydroxymercurialcompoundsbyoxymercurationdemercuration
reaction.2methyl1buteneyields:
a. 2methyl2butanol
b. 2methyl1butanol
c. Amixtureof2methyl2butanoland2methyl1
butanol
d. Noneofthegivenanswers

82. AsubstituentRwhichwithdrawselectronsfromthecarbocation
hasthefollowingeffect:
a. Itdestabilizesthecation
b. Itstabilizesthecation
c. Itmakesthecationstructuretetrahedral
d. Noneofthegivenanswers

83. Thistestwillshowwhetheranamineisprimary,secondary,or
tertiary:
a. Periodictest
b. Sangerstest

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c. Lucastest
d. Benedictstest
e. Hinsbergstest

84. Whichaminoacidprovideskinksinthestructureofproteins?
a. Cysteine
b. Cystine
c. Histidine
d. Proline

85. Thehydrolysisofonemoleofmannosegives:
a. 2molesglucose
b. 1moleglucose+1molegalactose
c. 2molesGalactose
d. 1molefructose+1moleglucose
e. Noneofthese

86. HClhasahigherbonddissociationenergythan:
a. HBr
b. H2
c. HF
d. HOH

87. Thecarboxylateanioncontainssigmabondsthatutilize:
a. sp3orbitals
b. porbitals
c. sporbitals
d. sp2orbitals
e. dorbitals

88. C6H12belongstoaseriesofhydrocarbonsknownas:
a. Arenas
b. Alkanes
c. Alkenes
d. Alkynes
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e. Nocorrectanswers

89. Whichofthefollowingconvertsacetaldehydetoaceticacid?
a. Sodiumborohydride
b. Hydrogen/Ni
c. Potassiumpermanganate
d. Lithiumborohydride
e. Nametal

90. Whatisthemajorproduct(s)ofdehydrationof
(CH3)2C(OH)CH2CH3?
a. CH2=CHCH3
b. CH2=C(CH3)CH2CH3
c. (CH3)2C=CHCH3
d. (CH3)2CHCH=CH2
e. Noneofthegivenanswers

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