Organic Chemistry Board Exam Questions
Organic Chemistry Board Exam Questions
Organic Chemistry Board Exam Questions
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
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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
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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
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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
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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