Chemistry 130, Final Exam Instructor: Bergdahl

Spring 2019

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PartA.1‐50Questions.Eachcorrectis3points.(Part1max150points)1)Themajorproductofthebelowreactionwillbe

2)Themajorproductofthebelowreactionwillbe

3)Theproductofthereactionbelowis

A)

B)

C)

D)

OH

OH

OH H2SO4/H2O

A)

B)

C)

D)

HCl

HO

no reaction

Cl

A)

B)

C)

D)

O

NaSMe

OH

MeS

OH

MeS

SMe

HO

SMe

HO

4)EpoxidesaregoodelectrophilesbecauseA)RO‐isagoodleavinggroupB)EpoxideopeningafternucleophilicattachrelievesalotofringstrainC)Theyarenotgoodelectrophiles.D)Therearenostericsbecauseofthesmall3memberedring5)AnalkaloidisA)AnopioidfromnatureB)AcomplexmoleculefoundinnaturewithabunchofheteroatomsinitC)AbasicmoleculefoundinnaturewithnitrogenatomsinthestructureD)Aneutralmoleculefoundinnaturewithoxygenatomsinthestructure6)Whichofthebelowcompoundsis2,4‐dimethylaniline

7)Whichofthemoleculesbelowis(R)‐1‐phenyl‐1‐propanamine

8)Whichcompoundwillhavethehighestboilingpoint.A)C2H6B)CH3NH2C)CH3OHD)CH3OCH3

9)Whichcompoundisthebetterbase.A)C2H6B)CH3NH2C)CH3OHD)CH3OCH3

A)

B)

C)

D)

NH2

NH2

OH

O

A)

B)

C)

NH2

NH2

NH2

D)

NH2

10)Whyarealcoholsworsebasesthanamines?A)Becausenitrogenismoreelectronegative,thelonepairofelectronsismoreeasilysharedB)Becausenitrogenislesselectronegative,thepositivechargeintheconjugateacidismorestablewithaminesC)Actually,alcoholsarealwaysstrongerbasesthanamines.11)TheKeqforthebelowreactionis

A)1B)greaterthan1C)lessthan112)Whichofthefollowingaminesisthestrongestbase?

13)Why?A)ResonancestabilizesthelonepairofelectronsonthebasicnitrogenB)ElectronegativityC)ResonancedestabilizesthelonepairofelectronsonthebasicnitrogenD)Theinductiveeffect14)Theoxygeninahydroxylgroupis_____hybridizedandhasbondanglesof____A)sp,180B)sp3,120C)sp2,120D)sp3,109.5

15)WhichmoleculebelowisR‐2‐pentanol

NH2

O

OH

NH3

O

O

N NH

NH2NH2 NH2

A) B)C)

A)

B)

C)

D)

OH

OH

OH

O

16)WhatistheelectronconfigurationofaneutralNitrogenatom?A)1s22s22p5B)1s22s22p3C)1s22s22p4D)1s22s22p217)Molecule_______isenoltaoutomerandtheKeqofthisreactionis____

A)A,greaterthan1B)B,greaterthan1C)A,lessthan1D)B,lessthan118)Thenameofthefollowingmoleculeis

A)2‐methylbutanoicacidB)3‐methylbutanoicacidC)2‐methylpropanoicacidD)isovalericacid19)3‐methylbenzoicacidis

20)Whichcarbonreferstothealphacarbon?

21)WhichAcidisthemostacidic

22)Thecarboninacarbonylgroupis_____hybridizedandhasapartial____A)sp,positivechargeB)sp2,positivechargeC)sp2,negativechargeD)sp3,positivecharge

23)whichmoleculebelowispentanal

24)aldehydesaregenerally_________polarthanketonesA)LessB)MoreC)similarly25)Alcoholshave_________boilingpointsthancomparablysizedaldehydes/ketonesA)HigherB)Lower

26)Predictthemajorproductfromthebelowreaction

27)Whichofthefollowingaminesisprimaryaliphatic

28)Theproductofthereactionbelowis

29)alcoholsare_______acidicthanthiolsA)moreB)Less

NH3

A)

B)

C)

NH2

NH2

NH2

D)

NH2

Br

A B C D

N

NMe N

H

O

OH

H2NOH

O

NH3

A)

B)

C)

D)

O

HCl

OH

Cl

OH

Cl

Cl

HO

Cl

HO

30)Thecompoundsbeloware

A)ConstitutionalIsomersB)EnantiomersC)DiastereomersD)GeometricIsomersE)thesamemolecule31)Thecompoundsbeloware

A)ConstitutionalIsomersB)EnantiomersC)DiastereomersD)GeometricIsomersE)thesamemolecule32)EnantiomersareA)SuperposablemirrorimagesB)Non‐superposablemirrorimagesC)Moleculesthathavethesameconnectivitybutadifferentorientationofatomsin3‐dimensionalspaceD)Moleculesthathavethesamemolecularformulabutadifferentconnectivity.33)Howmanypossiblestereoisomersdoesthecompoundbelowhave?

A)2B)6C)8D)12

34) Isinthe_____configurationA)SB)R

I

ClBr

35)Thestereocentersinthebelowmoleculeareinthe________configuration

A)S,SB)R,RC)R,SD)S.RE)noneoftheabovebecausemoleculeisnotchiral36)Whichofthecompoundsbelowwillhavethelowestboilingpoint

37)HowmanystepsarethereinthemechanismofaSN1nucleophilicdisplacementreaction?A)1B)2C)3D)438)Thereactionbelowisa______

A)SN1B)E1C)SN2D)E2

OH

OH

A)

B)

C)

D)

OH

OH

OH

O

OH

39)Thereactionbelowisa______

A)SN1B)E1C)SN2D)E240)Thereactionbelowisa______

A)SN1B)E1C)SN2D)E241)WhichofthebelowanionsisthebestleavinggroupA)I‐B)Br‐C)Cl‐D)F‐42)WhichofthefollowingstepsistheratedeterminingstepofanSN1reactionis

43)Pleasepredictthemajorproductformthebelowreaction

BrO

Br

SS

44)Themoststablecarbocationbelowis

45)Predicttheproductofthebelowreaction

46)Predicttheproductofthebelowreaction

47)Whichofthebelowalkeneswillhavethehighestboilingpoint?

48)Whichofthefollowinghydrocarbonsisleastacidic?

49)TheIntermediateinthereactionprofilebelowcorrespondsto_______

50)Predicttheproductofthebelowreaction

PartB.Shortanswerquestions,51‐60,eachproblemisworth8‐15points(total100points)Problem51.SelectthememberofeachpairthatshowsthegreaterrateofSN2reactionwithKIinacetone.(8p)(a)

(b)

(c)

(d)

Problem 52. Predictthepositionofequilibriumforeachacid‐basereaction;thatis,doeseachlieconsiderablytotheleft,doeseachlieconsiderablytotheright,oraretheconcentrationsevenlybalanced?(UselettersL,RorEabovetheequilibriumarrowsfora‐d)(8p)(a) CH3CH2OH+Na+OH−⇌CH3CH2O−Na++H2O

(b) CH3CH2SH+Na+OH−⇌CH3CH2S−Na++H2O

(c) CH3CH2OH+CH3CH2S−Na+⇌CH3CH2O−Na++CH3CH2SH

(d)

Problem53.Drawastructuralformulaforeachcompound(givenareIUPACnames).(9p)(a)3‐Aminopropene(b)(R)‐2‐pentanol(c)meso‐1,2‐Dibromocyclopentane

Problem54.Selectthememberofeachpairthatundergoesnucleophilicsubstitutioninaqueousethanolmorerapidly.(9p)(a)

(b)

(c)

Problem55.ProvideanIUPACorcommonnameforthemoleculesbelow(15p)(a)

(b)

(c)

(e)

(f)

Problem56.Epibatidine(below),acolorlessoilisolatedfromtheskinoftheEcuadorianpoisonfrogEpipedobatestricolor,hasseveraltimestheanalgesicpotencyofmorphine.Itisthefirstnonopioid(nonmorphine‐likeinstructure)analgesiceverisolatedfromanaturalsource.(8p)

(a) Whichofthetwonitrogenatomsofepibatidineisthemorebasic?

(b) Markallstereocentersinthismolecule.Problem57.Fromeachpairofcompounds,selectthestrongerbase.(12p)

Problem58.Procainewasoneofthefirstlocalanestheticsforinfiltrationandregionalanesthesia.ThehydrochloridesaltofprocaineismarketedasNovocaine®.(6p)

(a)Whichnitrogenatomofprocaineisthestrongerbase?

(b)DrawtheformulaofthesaltformedbytreatingprocainewithonemoleofHCl.

(c)Isprocainechiral?WouldasolutionofNovocaine®inwaterbeopticallyactiveoropticallyinactive?

Problem59.Classifyeachaminogroupasprimary,secondary,ortertiary

andasaliphaticoraromatic.(10p)

Problem60.WritetheIUPACnameforeachcompoundbelow.(15p)(a)

(b)

(c)

(d)

(e)

Grading: PartA____________/150points PartB_____________/100points Total______________/250points