Chemistry231FinalExam Name___________________________________

November17,2009

MULTIPLECHOICE.Choosetheonealternativethatbestcompletesthestatementoranswersthequestion. 1) Allylicandbenzyliccarbocationsaregreatlystabilizedby: A) hyperconjugation B) inductiveeffects C) resonance D) nucleophilicity 2) Threeofthefivereactionsthatfree-radicalsundergoare: A) substitution B) disproportionation atomabstraction fragmentation displacement atomabstraction C) propagation combination termination D) termination eliminaation addition 1)

2)

3) Anucleophileis: A) aprotondonor B) anelectronpairacceptor C) aLewisbase D) aBronstedbase E) aLewisacid 4) RankthefollowingmoleculesinorderofincreasingrelativerateofS N1solvolysiswithmethanol andheat(slowesttofastestreacting).

3)

4)

A) 2<3<4<5<1 B) 3<2<4<5<1 C) 1<2<5<4<3 D) 2<3<4<1<5 E) 5<4<3<2<1 5) ALewisAcidisa: A) protondonor B) protonacceptor C) electronpairacceptor D) anelectrophile E) bothCandD 1 5)

6) Howmanydistinctdichlorinationproductscanresultwhenisobutaneissubjectedtofreeradical chlorination? A) 1 B) 2 C) 3 D) 4 E) 6 7) Towhichconformationofbutanewouldthepositionmarkedwithanastetiskinthefollowing energydiagramcorrespond?

6)

7)

A) anti B) eclipsed,HandCH3 C) gaucheD) eclipsed,CH3andCH3 E) gauche+ 8) When3-iodo-3-ethylpentaneistreatedwithsodiummethoxideinmethanol,themajororganic productisan__________thatisgeneratedthroughan__________mechanism. A) alkene,E2 B) ether,SN1 C) alkene,E1 D) ether,SN2 E) ether,E1 9) WhichofthefollowingalkylhalidesismostlikelytoundergorearrangementinanS N1reaction? A) 3-bromopentane B) 1-bromo-4-methylcyclohexane C) bromocyclohexane D) 2-chloro-3,3-dimethylpentane E) 3-chloropentane 8)

9)

10) Whichofthefollowinglineorbitalenergydiagramsdescribestheorbitallocationofvalence electronsinansp3 hybridizedcarbonatom(considerthatSPisagenericnotationthatcould referenceeithersp,sp2 orsp3hybridorbitals)? A)

10)

B)

C)

D)

E)

11) Theorderofrelativestabilityofcarbocationsis: A) 1 o>2o>3 o>methyl C) 3 o>2o>1o>methyl

11) B) methyl>3o>2o>1o D) 1 o>3 o>2 o>methyl 12)

12) Rankthefreeradicals(I-III)shownbelowinorderofdecreasing stability(i.e.,frommoststableto leaststable).

A) II>I>III

B) I>II>III

C) II> III> I

D) III> II> I

E) I>III> II

13) Predictthetwomostlikelymechanismsforthereactionof2-iodohexanewithsodiumethoxide. A) E1andSN1 B) E2andSN1 C) SN2andSN1 D) SN2andE2 E) E1andE2 14) Inthefirstpropagationstepofthefreeradicalchlorinationofmethane,whichofthefollowing occurs? A) AcarbonradicalreactswithCl2 B) Cl2 dissociates C) Twochlorineradicalscombine D) Acarbonradicalreactswithachlorineradical E) Achlorineradicalabstractsahydrogen 15) Whichofthecompoundsbelowundergoessolvolysisinaqueousethanolmostrapidly? A) isopropylchloride B) 3-chloropentane C) cyclohexylbromide D) methyliodide E) 3-iodo-3-methylpentane 16) Whichofthefollowingtermscomesclosesttodescribinganelectrophile? A) Lewisbase B) nucleophile C) nonpolar D) anion E) Lewisacid 17) Whichofthemoleculesshownbelowisbicyclo[4.2.0]octane

13)

14)

15)

16)

17)

A)

B)

C)

D)

TRUE/FALSE.WriteTifthestatementistrueandFifthestatementisfalse. 18) Thebromideionisastrongerbasethatthefluorideion. MULTIPLECHOICE.Choosetheonealternativethatbestcompletesthestatementoranswersthequestion. 19) WhichofthefollowingalkylchlorideswillundergoS N2reactionmostreadily? A) 1-chloro-4-methylpentane B) 2-chloro-4-methylpentane C) 3-chloro-2-methylpentane D) 2-chloro-2-methylpentane E) 2-chloro-3-methylpentane 20) Inwhichofthefollowingmechanisms(S N1,SN2,E1,E2)arealkenesthemajorreactionproducts? A) SN1only B) E2only C) SN2only D) E1only E) bothE1andE2 21) Whichofthefollowingmechanisms(S N1,SN2,E1,E2)feature(s)acarbocationintermediate? A) SN2only B) E1only C) E2only D) SN1only E) bothSN1andE1 22) Whichofthefollowingstatementscorrectlydescribe(s)E1reactionsofalkylhalides(RX)? I. Rate=k[base] II. Rate=k[base][RX] III. Rate=k[RX] IV. Thereactionsoccurintwoormoredistinctsteps. V. Rearrangementsaresometimesseen. A) III,IV,andV B) I,IV,andV C) IIIandV D) Ionly E) IIandIV 23) Whichofthelabeledatomsinthefollowingstructurearesp 2 hybridized? 23) 19) 18)

20)

21)

22)

A) 2and4

B) 1and4

C) 2,3and4

D) 2and3

E) 2and5

TRUE/FALSE.WriteTifthestatementistrueandFifthestatementisfalse. 24) TheE1andE2reactionshaveacommonmechanisticintermediate. MULTIPLECHOICE.Choosetheonealternativethatbestcompletesthestatementoranswersthequestion. 25) Whichofthefollowingcompoundsisnot aconstitutionalisomerofacompoundwithanempirical formulaC3 H7 Oandaformulamassof118.164? A) 25) 24)

B)

C)

D)

E)

26) When(cis)-1-bromo-2methylcyclohexaneistreatedwithmethanolandheat,fourdifferent productsareformed-twobysubstitutionandtwobyelimination.

26)

Whichofthefollowingconditionswouldchangetheoutcomeofthisreactionbypromotingthe productionof3-methylhexeneasthemajorproduct?

A) tert-butoxide/tert-butylalcohol B) KOH,ethanolandheat C) methoxide/methanol D) water/acetoneandheat E) tert-butylalcoholandheat 27) Inaccordancewithvalenceshellelectronpairrepulsiontheory(VESPR),thegeometryofa moleculesurroundedbythreeelectrondomainsis anditshybridizationis . A) trigonalplanar,sp3 C) trigonalplanar,sp2 B) tetrahedral,sp 2 D) tetrahedral,sp 3 27)

TRUE/FALSE.WriteTifthestatementistrueandFifthestatementisfalse. 28) TheSN1andE1reactionshaveacommonmechanisticintermediate. MULTIPLECHOICE.Choosetheonealternativethatbestcompletesthestatementoranswersthequestion. 29) Predictthetwomostlikelymechanismswhichoccurwhen2-iodohexaneisheatedinethanol. A) SN2andE2 B) E1andSN1 C) E2andSN1 D) E1andE2 E) SN2andSN1 29) 28)

30) Whichofthestatementsbelowcorrectlydescribesthechairconformationsof trans-1,4-dimethylcyclohexane? A) Thelowerenergychairconformationcontainsoneaxialmethylgroupandoneequatorial methylgroup. B) Thehigherenergychairconformationcontainstwoaxialmethylgroups. C) Thehigherenergychairconformationcontainsoneaxialmethylgroupandoneequatorial methylgroup. D) Thetwochairconformationsareofequalenergy. E) Thelowerenergychairconformationcontainstwoaxialmethylgroups.

30)

AnswerKey Testname:CHEM231FINALEXAMVERSION1

1) C 2) B 3) C 4) D 5) E 6) C 7) B 8) A 9) D 10) E 11) C 12) E 13) D 14) E 15) E 16) E 17) C 18) FALSE 19) A 20) E 21) E 22) A 23) D 24) FALSE 25) A 26) A 27) C 28) FALSE 29) B 30) B