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Stereochemistry
Note,thetermstereogeniccenterisusedanalogouslytochiralcenter.
1.Thespatialorientationoftheatomsofamoleculeiscalleditswhat?
A)constitution B)configuration C)handedness D)composition
2.Anobjectthathasnoelementofsymmetryiscalledwhat?
A)tetrahedral B)achiral C)symmetric D)asymmetric
3Stereoisomersdifferfromeachotherinwhatrespect?
A)composition.
B)constitution
C)configuration
D)sterichindrance
4Whichofthefollowingmustbetrueforanopticallyactivecompound?
A)themolecularconfigurationisachiral
B)themolecularconfigurationischiral
C)thecompoundisaracemicmixtureofenantiomers
D)themolecularconfigurationmusthavetwoormorestereogeniccenters
5Enantiomersare?
A)stereoisomershavingnonidenticalmirrorimageconfigurations
B)stereoisomersthatdonothavenonidenticalmirrorimageconfigurations
C)stereoisomershavingamirrorplaneofsymmetry
D)achiralstereoisomers
6WhichconformationofcyclohexanehasaC3axisofsymmetry?
A)boat
B)twistboat
C)chair
D)envelope
7Thefollowingcompoundhashowmanystereogeniccenters?

A)0
B)1
C)2
D)3
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8Hydration,byoxymercuation,of3methyl1butenegives3methyl2butanol.
Whatistheobservedrotationofthisproduct,usinga20%solutioninethanolina1dmpolarimetercell?.
Assumethespecificroatationofthepure(S)enantiomertobe+16
A)+3.2
B)3.2
C)180(+or)
D)0
9Whichofthefollowingis(R)3hexanol?

10WhichtwoFischerformulasrepresentapairofenantiomers?

A)I&II
B)III&IV
C)I&IV
D)II&III
11ConsidertheFischerprojectionformulafor(S)2chlorobutane
Whichofthefollowingchangesdoesnotconvertthisstructuretothe(R)enantiomer?
A)rotation180intheplaneofthepaper(orscreen)
B)flippingthestructureover(a180rotationoutoftheplane)
C)exchangingthetwoverticalsubstituents(i.e.topandbottom)
D)exchangingthetwohorizontalsubstituents(i.e.rightandleft)
12Whichofthefollowingrepresents(E)3,6dichloro6methyl3heptene?

13DesignatetheCIPpriorityorderofthefollowingC5H11groups.(Lowest<Highestpriorityorder)
ICH3(CH2)4II(CH3)3CCH2IIIC3H7CH(CH3)IV(CH3)2CHCH2CH2
A)I<II<III<IV
B)IV<III<II<I
C)I<IV<II<III
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D)III<II<IV<I
14Whichofthefollowingcompoundshastwostereogeniccenters(asymmetriccarbons)?

15Whichofthefollowingcompoundsis(S)4chloro1methylcyclohexene?

16Whichtwoofthefollowingcompoundsrepresentsapairofenantiomers?

A)I&II
B)II&III
C)III&IV
D)II&IV
17Whichofthefollowingisproperlyclassifiedasamesocompound?

18WhenHOBraddsto4methylcyclopentene,howmanynewstereogeniccentersareformed?
A)1
B)2
C)3
D)4
19Whichofthefollowingisomericdienesischiral?
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A)2,3pentadiene
B)3methyl1,2butadiene
C)2methyl1,3butadiene
D)none,allareachiral
20Whichtwoofthefollowingcompoundsarediastereomers?

I&II
II&IV
III&IV
I&III
21Twoequivalentsofbromineaddtooneequivalentof1,7octadiene.
Howmanystereoisomerictetrabromideswillbeformed?
A)1
B)2
C)3
D)4
22TwoequivalentsofOsO4hydroxylateoneequivalentof1,5cyclooctadiene.
Howmanystereoisomericcyclooctane1,2,5,6tetraolswillbeformed?
A)1
B)2
C)3
D)4
23Theopticallyactivebromohydrin(1R,2R)2bromocyclohexanolreactswithbasetoproducecyclohexene
oxide(C6H10O).
Whichofthefollowingstatementsistrue?
A)aracemicproductisformed
B)theobservedopticalrotationchangessign
C)theobservedopticalrotationdoesnotchangesign
D)theproductisachiral
24Whichofthefollowingsugarshastheconfiguration(2S,3R,4R)?

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25Howmanystereogeniccarboncentersarethereinmorphine,structureshownbelow?

A)4
B)5
C)6
D)7

26Pure(S)2butanolhasaspecificrotationof+13.52degrees.
Youhavemadeandpurifiedasamplethathasacalculatedspecificrotationof+6.76degrees.
Whatcanyouconcludeaboutthissample?
A)thesamplehascompletelyracemized
B)50%thesamplehasrearrangedintoamesoisomer
C)50%ofthesamplehasracemized
D)75%ofthesamplehasracemized
27Howmanystereoisomersof(CH3)2CHCH=CHCH2CH(OH)CH2Brarepossible?
A)2
B)3
C)4
D)5
28Iftwoisomershavebeenclassifiedcorrectlyasepimers,theymayalsobecalled...?
A)diastereomers
B)enantiomers
C)tautomers
D)conformers
29
Thedrawingontherightshowsthatcis1,2dichlorocyclohexane
ischiral.
Effortstoresolvethiscompoundfail.Why?

A)thecisandtransisomersrapidlyinterconvert.
B)thecompoundisactuallyamesostructure.
C)thechairconformersrapidlyinterconvertproducingaracemicmixture.
D)methodsforresolvingalkylchloridesarenotavailable.
30Whichofthefollowingstatementsmustbetruefortwopurechiralisomers?
A)theymustbeenantiomers
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B)theymustbediastereomers
C)theymustbestereoisomers
D)theymustbeopticallyactive
31Whichtwoofthefollowingcompoundsareidentical?

A)I&II
B)II&IV
C)III&IV
D)I&III
32
Thestructuralformulaontherightisthatofcamphor.
Whichofthefollowingstatementsiscorrect?
A)Thiscompoundhastwostereogeniccentersandexistsasapairofenantiomers.
B)Thiscompoundisachiral.
C)Thiscompoundhasthreestereogeniccentersandexistsasapairofenantiomersandamesoisomer.
D)Thiscompounddoesnothaveanenantiomer
33Whichofthefollowingstatementsistrueforapairofdiastereomers?
A)theywillhaveidenticalphysiologicalproperties.
B)theywillhavespecificrotationsofoppositesign.
C)theywillhaveidenticalchemicalproperties(e.g.reactivity)
D)theywillhavedifferentphysicalproperties.
34Whichofthefollowingdescriptivetermswouldneverbeappliedtoapairofstereoisomers?
A)enantiomers
B)tautomers
C)diastereomers
D)epimers
35Whatkindofreagentwouldbeneededtoresolvearacemicamine,suchas2aminobutane?
A)thepureopticallyactiveaminetoserveasatemplateforcrystallization.
B)anachiralcarboxylicacidtogivearacemicmixtureofaminesalts.
C)anenantiomericallypurechiralcarboxylicacidtogiveadiastereomericmixtureofaminesalts.
D)aracemicchiralcarboxylicacidtogiveacompletemixtureofisomericaminesalts.
36Whatcommonsymmetryelementsifanyarefoundinthestablechairconformeroftrans1,4
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dichlorocyclohexane?
A)asinglemirrorplaneandaC2rotationalaxis.
B)aC3rotationalaxisbutnomirrorplane.
C)twoorthogonalmirrorplanesandaC2rotationalaxis.
D)asingleC2rotationalaxisbutnomirrorplane.
37Whatcommonsymmetryelementsifanyarefoundinthestablechairconformeroftrans1,2
dichlorocyclohexane?
A)asinglemirrorplaneandaC2rotationalaxis.
B)asinglemirrorplaneandaC3rotationalaxis.
C)twoorthogonalmirrorplanesandaC2rotationalaxis.
D)asingleC2rotationalaxisbutnomirrorplane.
38Reactionof3methyl1,4cycloheptadienewithexcessperbenzoicacid(C6H5CO3H)formsadiepoxide
product.
Howmanystereoisomers,countingenantiomers,areexpectedfromthisreaction?
A)4(twopairsofenantiomers)
B)4(twomesocompoundsandapairofenantiomers)
C)5(twopairsofenantiomersandamesocompound)
D)6(twopairsofenantiomersandtwomesocompounds)
39Theantimalarialalkaloidquinine,C20H24N2O2,isopticallyactive.
Anethanolsolutionof8gquininein100mLdisplaysarotationof13.6ina1dmpolarimetertube.
Whatisthespecificrotationofquinine?
A)85
B)170
C)43
D)26
40AC7H14OopticallyactivealcoholisoxidizedbyJones'reagenttoanopticallyinactive(achiral)ketone.
Whichofthefollowingcompoundsmeetsthesefacts?

41Whichofthefollowingcompoundshasaprochiralmethylenegroup(i.e.thehydrogenatomsare
diastereotopic)?
A)propane,CH3CH2CH3
B)cyclopropane,(CH2)3
C)2methylpropene,CH2=C(CH3)2
D)ethanol,CH3CH2OH
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42Thethermalelectrocyclicclosureof(2E,4Z,6E)2,4,6octatrienegiveswhichofthefollowing?
A)cis5,6dimethyl1,3cyclohexadiene
B)trans5,6dimethyl1,3cyclohexadiene
C)cis3,6dimethyl1,4cyclohexadiene
D)cis3,6dimethyl1,4cyclohexadiene
43TheCoperearrangement,[3,3]sigmatropicshift,ofmeso3,4dimethyl1,5hexadienegiveswhichofthe
following?
A)1,7octadiene
B)(2Z,6Z)2,6octadiene
C)(2E,6Z)2,6octadiene
D)(2E,6E)2,6octadiene
44WhichistheexpectedproductfromthefollowingDielsAlderreaction?

45Whichofthefollowingstructuresrepresentsachiralcompound?

46WhichofthefollowingcompoundshasaSconfiguration?

47Howshouldthefollowingstructureofpolypropylenebeclassified?

A)isotactic
B)syndiotactic
C)atactic
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D)headtohead
48WhichofthefollowingC8H16isomersisthermodynamicallymoststable?

49Whichofthefollowingstatementsisnotanessentialfeatureofanopticallyactivecompound?
A)themoleculesofanopticallyactivecompoundwillbedissymetricorasymmetric.
B)themoleculesofanopticallyactivemoleculemusthaveatleastonestereogenicsite.
C)anopticallyactivecompound'smolecularconfigurationwillnotbeidenticalwithitsmirrorimage.
D)anopticallyactivecompoundwillhaveatleastonestereoisomer.
50Whichofthefollowingstatementsisnotcorrect?
A)apairofenantiomericcompoundswillhavethesamemeltingpoint.
B)apairofenantiomericcompoundswillhavethesamesolubilityinethanol.
C)apairofenantiomericcompoundswillhaveexactlythesamefunctionalgroups.
D)apairofenantiomericcompoundswillhaveidenticalopticalrotations.
51Whichofthestructuresontheright,ifany,representssyndiotacticpolyacrylonitrile?

52Examinethecompoundontheright.
Howmanystereoisomershavingthisconstitutionarepossible?

A2

B4

C6

D8

53Whichofthefollowingis(2R,3S)2,3pentanediol?

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