Why don't identical twins have identical fingerprints? Done by Nechaeva Nastya.
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Chemistry233Chapter5ProblemSet
1) Foreachofthefollowingpairsofcompounds,determinewhethertheyareidentical,
constitutionalisomers,orstereoisomers.Ifstereoisomers–specifywhethertheyareenantiomersordiastereomers.
2) Foreachcompoundbelow,identifyallchirality(asymmetric)centerswithanasterisk(*).
O O
O
O
OH OH
OH OH
Cl
H3CH3C Cl
Cl
OH
ClO
OH
Br
OHBr
CH3
rois identicaltroisstereoisomers
diastocomers
stereoisomers stereoisomerenantiomersdiastveomers
stereoisomers identicaldiastocomers
cistranscis stereoisomersstereoisomers
trans diastocomersdiastocomers
Answer Key
Chem.233–Chapter5ProblemSet
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3) Drawtheenantiomerofeachcompoundbelow.
4) AssignanR/Sconfigurationtoeachchiralcenterinthecompoundsbelow.
OHCl
Cl F
OH
CHOOHHOHHHHOOHH
CH2OH
CH3
F OHH Br
H
H
OH
Cl Cl
HO OH
OHOO
O
NH2
O ClOO Cl
ClCl
HD
Neitherdrawthemirrorimage or invert AI chiralCentos
HICB ftp
siHgh I HOT Brl to l sBH
I CHOI Ho H
OH I HO Hi I H HI l Ho H
I CHOH
i EM i inhere I justinverted 1 Y
chiralCentos 1all
iiOH 1 IfCleary 1 RTto i LI s
I
4I y
3 I 4wilt 41 Ez 3 3 2
Trick lookslikeBbut 4 group is pointingout so it is actually
Deuterium D 34J 2 3isnhis.gg its fake T.fr guy
2 3y l i z
Looks s butmy Looks s but 4 isis out soit'sreally out so it'sreallyrr
Chem.233–Chapter5ProblemSet
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5) ConverteachcompoundbelowtoaFischerProjectionusingthetemplatesprovided.Then,identifyeachchiralcenterwithanasterisk(*)anddrawtheenantiomer.
6) Identifyallasymmetriccentersinthemoleculesbelowandclassifythemoleculeaschiral,achiralormeso-achiral.
7) GiveanIUPACnameforeachofthecompoundsbelow.MakesuretoincludeR/Sdesignations.
OH
Cl
NH2
OHHH
Br
CH3
CH2CH3
HO
Cl
OH
Cl
OH
OH
ClOH
OH
OH
OH
Cl Cl
Br
CH3
Br HCH3
ClH
i cry OtherAcceptable answers for 1ststructureH Clb ClbI Ho H H 1017 cl OH 11 4
Cl Cl1 H OH
Clb i ab H Br
g Bri.tn rsr as t1 CHEB CHEB CHEB
Clb ClbI Clbab Ho H HO HH OHH i f i.ge Htkn eBH Nlt kN Hi
ab i NK Hi ab
ft11
chiral chiral achiral achiralHpo joµ Chiral
achiral meso1I II I
I1 achiral chiralachiral meso achiral meso achiral meso
Chiral achiral achiral chiral
1bromo 4s G ftp.Br
sty s r.fi BrLy4 3 z e z H 3 2R 3 G3 isopropyl I
IR 3R l bromo 3 isopropylcyclohexane 2h35 Z bromo 3Chlorobutane
Chem.233–Chapter5ProblemSet
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8) Indicatetherelationshipbetweeneachofthecompoundpairsbelow.Aretheyenantiomers,diastereomers,constitutionalisomers,oridenticalcompounds?
Cl
OH
F
OH
H
H
BrBr
F
H
HF
H
H
Br
H
Br
F
H
F
Br Br
Cl
Cl
Cl
Cl
CH3ClHClH
CH3
CH3ClHHCl
CH3
CH3OHHHCl
CH3 CH3
H OHCl H
CH3
OHH3C
CH3
OH
Cl Cl Cl Cl
OH OH
Rr6 2 R r z 3 4 s
s 3 2 4 i s4 I 3
IR zR 1,2dimethylcyclohexane R zChlorobutane ZR3s 2 fluoro3 methylpestaseorZR
Fault30Mts 8 6 I
z y s 6 7 s IRi s R 4 2103 R
25 SR 2 fluoro S isopropyloctane IR 2R l butyl1,2dimethylcyclohexane
diastereomers
T TOH enantiomers 4 OH
Thesearetwoidentical different
conformations identical
diastereomers
cis transdiastereomers
diastereomers
enantiomers
diastereomersenantiomers
Chem.233–Chapter5ProblemSet
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9) Labeleachofthefollowingaschiral,achiral,ormeso-achiral.
10) GivetherelationshipbetweenCompoundAandeachthesixcompoundsshownbelow.
11) AnswereachofthefollowingquestionsusingtheFischerprojectionsbelow.
a. Identifytheasymmetriccentersineach.
b. LabeltheR/Sconfigurationsateachasymmetriccenter.
c. Identifyapairofenantiomers_______________________
d. Identifyapairofdiastereomers_______________________
e. Whichifanyoftheabovecompoundsaremesocompounds?
BrBr CH3H CH3
H3C HCH3
CH3H Cl
H3C HCH3
CH3H ClH Cl
CH3
H
H
Br
ClClBr
CH3
HBrCH3
H CH3
CH3H OHH OH
CH3
CH3HO H
H OHCH3
CH3HO HHO H
CH3
OH
H3C OHH
H3CH
HH
OHHOCH3H3C
OH
HO CH3H
H3CH
OH
CH3HCH3
H OH
Compound A
CH2CH3
Br H
Br H
CH3
CH2CH3
Br H
H Br
CH3
CH2CH3
H Br
H Br
CH3
CH2CH3
H Br
Br H
CH3
A B C D
achiral meso achiralachiral Chiral
mustrotatearoundthesinglebondtoseesymmetryplane
fix Bru achiral
H H meso
chiral achiral meso chiralBritt DjBr
sR
constitutionalisomer identical diastocomer
achiral meso
r rr s
diastereomer identical identical
lusetrick1lookslike5 but 4 R J R s sisoutso t
horizontal
reallyE f out R R SS bydefinition
ofFischer
Aec BEDAers Bec AED CED
None