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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