chemistry 130, final exam
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Chemistry 130, Final Exam Instructor: Bergdahl
Spring 2019
Name:___________________________________________________ Be prepared to show ID upon request.
**Any use of any electronic devices is prohibited during the test** **
Be prepared to show ID upon request. My student I.D. (red I.D.) number is: Good Luck!!
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)
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)
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