Organic Chemistry

More documents

Recommendations

Info

Organic Chemistry - Ch 11 543 Daley & DaleyHOOCHOH 2 CCHNH2HH 2 NCCOOHCH 2 OHNatural serineSynthetic serineSome groups bonded to a stereocenter carbon are long chains.To determine whether the stereocenter is (R) or (S), continuesearching along these chains away from the stereocenter to the firstdifference between similar chains. Give the chains their prioritynumbers according to this difference.Solved Exercise 11.1Determine whether the following molecule has any stereogenic centers. Markall asymmetric carbon atoms and determine whether they have an (R) or (S)configuration.ClHCH 3OHSolutionThis molecule has three stereogenic carbon atoms. The carbon bearing the —OH group, the one bearing the —Cl and the one bearing the —CHClCH 3group. These three are starred in the following structure.Cl**HCH 3*OHThe carbon atom bearing the —CHClCH 3 has an (R) configuration.www.ochem4free.com 5 July 2005
Organic Chemistry - Ch 11 544 Daley & DaleyHClHRCH 3OHYou need to rotate the bond between the six-membered ring and the carbonbearing the —Cl group. Doing so helps to see that the atom has an (R)configuration.HClHCH 3HCH 3RClHOHOHThe carbon bearing the —OH group also has an (R) configuration. Flippingthe molecule 180 o helps to more clearly see the configuration of this carbonatom.ClH 3 CHRHO H(R,R,R)-3-(1-Chloroethyl)cyclohexanolExercise 11.3For each of the following examples, identify any stereogenic carbonatoms, and then determine whether they have (R) or (S)configurations.a)b)H 3 CHCOHCH 2 CH 3CH 3 CH 2BrCCH 3Hwww.ochem4free.com 5 July 2005
Page 1 and 2: Richard F. Daley and Sally J. Daley
Page 3 and 4: Organic Chemistry - Ch 11 532 Daley
Page 38: Organic Chemistry - Ch 11 567 Daley

Organic Chemistry

Create successful ePaper yourself

Delete template?

Save as template?