10/16/2015 Stereoisomerism

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SKILLBUILDER REVIEW
5.1IDENTIFYINGCISTRANSSTEREOISOMERISM

STEP1Identifyandnameallfourgroups STEP2Lookfortwoidenticalgroupsondifferentvinylicpositionsandassignthe
attachedtothe bond. configurationascisortrans.

TryProblems5.1,5.2,5.3,5.35

5.2LOCATINGCHIRALITYCENTERS

STEP1Ignoresp2andsphybridized STEP2IgnoreCH2andCH3 STEP3Identifyanycarbonatomsbearingfourdifferent

centers. groups. groups.

TryProblems5.4,5.5,5.6,5.34b,5.48

5.3DRAWINGANENANTIOMER

Eitherplacethemirrorbehindthe orplacethemirroronthesideofthe orplacethemirrorbelowthe

compound compound compound.

TryProblems5.7,5.8,5.33,5.34a,5.38af,il

5.4ASSIGNINGCONFIGURATION

STEP1Identifythefour STEP2Iftwo(ormore)atomsare STEP3Redraw STEP4Rotate STEP5Identifydirectionof

atomsattachedtothe identical,makealistofsubstituentsand thechirality moleculesothat 123sequence:clockwise
chiralitycenterand lookforthefirstpointofdifference. center,showing thefourth isR,andcounterclockwise
prioritizebyatomic onlythe priorityisona isS.
number. priorities. dash.

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10/16/2015 Stereoisomerism
TryProblems5.8,5.9,5.10,5.32,5.39ag,i,5.45

5.5CALCULATINGSPECIFICROTATION

EXAMPLECalculatethespecificrotationgiventhe STEP1Usethefollowingequation: STEP2Pluginthegivenvalues:

followinginformation:
sucrosedissolvedin ofwater

TryProblems5.12,5.13,5.14,5.15,5.16,5.44,5.50c,5.52

5.6CALCULATING%ee

EXAMPLEGiventhefollowinginformation,calculate STEP1Usethefollowingequation: STEP2Pluginthegiven

theenantiomericexcess: values:
Thespecificrotationofopticallypure
adrenalineis .Amixtureof(R)and(S)
adrenalinewasfoundtohaveaspecificrotation
of .Calculatethe%eeofthemixture.

TryProblems5.17,5.18,5.19,5.20,5.40,5.50a,b

5.7DETERMININGTHESTEREOISOMERICRELATIONSHIPBETWEENTWOCOMPOUNDS

STEP1Comparethe STEP2Ifallchiralitycentershaveoppositeconfiguration,thecompoundsareenantiomers.Ifonly
configurationofeachchirality someofthechiralitycentershaveoppositeconfiguration,thenthecompoundsarediastereomers.
center.

TryProblems5.21,5.22,5.36aj,l,5.41c,5.49a,c,ej

5.8IDENTIFYINGMESOCOMPOUNDS

Drawallpossiblestereoisomersandthenlookforaplaneofsymmetryinanyofthedrawings.Thepresenceofa
planeofsymmetryindicatesamesocompound.

TryProblems5.26,5.27,5.28,5.375.46,5.47,5.51,5.53a,b,d,fh

5.9ASSIGNINGCONFIGURATIONFROMAFISCHERPROJECTION

EXAMPLEAssignthe STEP1Chooseonehorizontallineand STEP2Prioritize. STEP3Rotateso STEP4Assign

configurationofthis drawitasawedge.Chooseonevertical thatthefourth configuration.
chiralitycenter. lineanddrawitasadash. priorityisona
dash.

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10/16/2015 Stereoisomerism

TryProblems5.29,5.30,5.31,5.39h,5.41a,b,5.43c,5.53c,e,5.54,5.55,5.56

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