1stSemesterOChem

PracticeFinalExam(2011)
I.Nomenclature
1.Thecorrectnameforthecompoundshownbelowis:
a.cis3bromo2,4hexadiene.
B r
b.(2Z,3Z,4E)3bromo2,4hexadiene.
c.(2E,4E)3bromo2,4hexadiene.
C H 3
C H 3
d.(E,Z,E)3bromo2,4hexadiene.
e.(2Z,4E)3bromo2,4hexadiene.
Br

C H

2.Whatisthecorrectnamefor:
a.3methylbromopentane
b.3bromomethylcyclohexane
c.cisbromomethylcyclopentane
d.cis1bromo3methylcyclopentane
e.1bromo3methylcyclopentane

Cl

3.Choosethecorrectnamefor:
a.Z3chloro2pentene
b.Z2chloro1methylbutene
c.trans3chloro2pentene
d.E3chloro2pentene
e.noneoftheabove
4.Whichmoleculeisanamide?
a.CH3CH(NH2)CO2H
b.(CH3)2CHC(NH)CH3
d.CH3NHCOCH3
e.noneoftheseareamides

c.CH3NHCH2OOH

5.Whichmoleculeisacarboxylicacid?
a.CH3CH(NH2)CO2H
b.(CH3)2CHC(NH)OCH3
c.CH3NHCH2OOH
d.CH3NHCOCH3
e.noneofthesearecarboxylicacids
6.Whichmoleculewouldbemostsolubleinhexane?
a.CH3CH(NH2)CO2H
b.(CH3)2CHCN
d.CH3NHCOCH3
e.H2O

c.(CH3)2NCH2OH

7.Thenumberofdegreesofunsaturationin2pentyn1olis:
a.1 b.2 c.3
d.4
e.cannotbedetermined
8.HowmanytertiaryH'sin2bromo3methylcyclohexanone(shownbelow)?
a.0
CH 3
b.1
c.2
Br

d.4
e.12
II.Stereochemistry
9.Whatpropertydoestrans1,3dimethylcyclobutanehavethatmakesitsmirrorimage
superimposable?
a.limitedsolubilityinnonpolarsolvents.
b.alowboilingpoint.
c.aplaneofsymmetry.
d.transrelationshipofsubstituents.
e.afourmemberring.
10.WhichofthefollowingcompoundshasanRconfiguration?

a.

c.

D
Ph
CH3

b.

Br
F
CH3

d.

OH

Cl
I

H
Ph

e.noneoftheabove
11.Whichmoleculehasthemostthermodynamicallyacidichydrogen?
a.

H O

c . P h C H (C H 3)C O C H

Ph

b.

C H 3C H (P h )C O O H

d.

O
Ph

e . n o a c i d i c H 's i n t h e s e m o l e c u l e s

12.Considertheproductsexpectedfromthereactionshown.Whichofthefollowing
statementsistrue?
a.Only2productswillbeformed.
CH3
b.Onlyonestereoisomerwillbeformed.
c.Aracemicmixtureofonealcoholisformed.
H+
d.Theproductswillberacemic.
D
H2 O

e.Theproductwillbeaketone.
13.Whichisapairofconformers?
a.
B r

B r

B r

b.
B r

Br
c.

B r

B r
d.

B r

III.ReactionsandMechanisms
14. WhichisthecorrectFischerprojectionfor(R)2bromobutane?
CH

a.

CH

B r

H 3C

H
H

b.

C H

B r

H
CH

c.

Br

C H

C H

d.
3

15.What'sthebestwaytocarryoutthereactionshown?
O H

a.
b.
c.
d.
e.

AddTsClandthenH2SO4andheat.
AddBr2inNaOHandthendehydrohalogenate.
AddKOHandheat.
AddH2SO4andheat.
Can'tbedonewithmodernorganicchemistry.

C H

B r
H

e . n o n e o f th e s e

16.Whatistheproduct(A)formedinthesequenceshownbelow?
N aN H 2
N a
C H 3I
1 ) O sO
C H 3O C H 2C C H
N H 3
2 ) H 2O
N H 3
a.

H O H
O
H O H

b.

H O H
O

+ e n a n tio m e r
H O H

c.

H O H
O

+ e n a n tio m e r
H O H

d.

H O H
O

H O H
e.I'veforgottentoomuchorganicchemistrytobeabletoanswer.
17.Whatreagentswouldyouusetocarryoutthefollowingtransformation:

H O
O

a.

H 2S O

b.

O H

N aO H

c.
O H

18.Whichisthebestwaytomake:
C O 2C H

C O 2C H

O N a
O H

e . c a n 't b e d o n e

d.
heat

O H

a.

KMnO 4

2 eq. CH3I

CH3OH
b.

CH 2 I2

O3

Zn

CH 2 Cl2

c.
CO 2CH3

heat

H2
Pd

CH3 O2 C

d.

AlCl3

KMnO 4

CH 3Cl
e.

AlCl3

KMnO4

CH 3Cl

Li
NH3

19.Thebestwaytomakethecompoundshownbelowfromcyclopenteneis:
O H

O H
a.B2H6thenH2O2,NaOH
b.2equivalentsofacidandwater
c.hotKMnO4
d.OsO4thenwater
e.peracidfollowedbyaqueousacid
20.Whichofthefollowingmonomersgivesthepolymershownbelow?

a.

c.

b.

e . c a n 't b e d o n e

d.

21.Whichstructureisanintermediatebromoniumion?
OCH3
Br
c.

b.

a.

Ph

Br
O

FeBr2
Br

d.

e.
Br

22.WhichisthecorrectorderofthefollowingcompoundsADaccordingtobase
strength(i.e.strongestbasefirst)?

OLi

PhLi
A

CH3 CH2 ONa

B

a.C>B>A>D b.C>A>B>D

c.A>C>D>B d.A>D>B>C

23.Determinethemajorproductfromthereactionshown.

Ph

1 eq.
HCl
ether
heat

NaNH2
D
e.D>A>B>C

C l

a.

c.

b.
Ph

Ph

Ph
Cl

Cl
Cl
d.

e . n o n e o f th e a b o v e
Ph

24.Themajorproductforthereactionshownbelowis:

OH

NaH

CH 3I

THF
a.3penten2olb.2butenec.methanold.1methoxy2butenee.2pentene
25.Whichofthefollowingisaterminationstepforaradicalreaction?
a.R+O2
c.R+OOH
b.RH+O2

d.R +alkene
e.noneoftheabove
26.HowmanysignalswilltheprotonNMRof1,1dichlorocyclopentanehave?
a.1
b.2
c.3
d.4
e.5
27.Analkenewillreactwithelectrophiles.Amonosubstitutedalkenewillbe
a.moreacidicthanatrisubstitutedalkene.
b.lessnucleophilicthanatetrasubstitutedalkene.
c.lessnucleophilicthanaterminalalkyne.
d.moreacidicthanaterminalalkyne.
e.noneoftheabove.
28.Predictthemajorfinalproductforthefollowingreaction:
O H
c a t. H

heat

29.Whichofthecarbocationsismorestableandwhy?

a.A,becauseofhyperconjugation.
b.B,becauseithaslessbranching.
c.C,becauseresonanceismorestabilizingthanhyperconjugation.
d.A,becauseBandCaresecondarycarbocationsandoxygeniselectronegative.
e.Theyareallthesamestability.
30.AlkylhalidescanundergoeliminationbytheE1ortheE2mechanism.Whichofthe
followingstatementsistrueaboutthenatureofthealkylhalideintheseelimination
reactions?
a.Bothreactionpathsfollowtherate:1RX>2RX>3RX
b.E1follows3RX>2RX>1RXandE2follows1RX>2RX>3RX
c.E1follows1RX>2RX>3RXandE2follows3RX>2RX>1RX
d.Bothreactionpathsfollowtherate:3RX>2RX>1RX
e.Noneoftheabove.